2-Chlorobenzonitrile by Asch

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Synthesize Find similar

Rx-ID: 2157329 Find similar reactions

97%

With N-trifluoroacetylimidazole in tetrahydrofuran

3.5 h; Heating;

Keumi, Takashi; Yamamoto, Takayoshi; Saga, Hiroshi; Kitajima, Hidehiko

Bulletin of the Chemical Society of Japan, 1981 , vol. 54, # 5 p. 1579 - 1580 Title/Abstract Full Text Show Details

97%

With cerium(IV) oxide in o-xylene

T=160°C; 0.5 h; Dean-StarkInert atmosphere;

Rapeyko, Anastasia; Climent, Maria J.; Corma, Avelino; Concepción, Patricia; Iborra, Sara

ACS Catalysis, 2016 , vol. 6, # 7 p. 4564 - 4575 Title/Abstract Full Text View citing articles Show Details

96%

With phosphoric acid diethyl ester 2-phenylbenzimidazol1-yl ester; triethylamine in acetonitrile T=20°C; 0.416667 h;

Kokare, Nagnnath D.; Shinde, Devanand B.

Monatshefte fur Chemie, 2009 , vol. 140, # 2 p. 185 - 188 Title/Abstract Full Text View citing articles Show Details

95%

With thionyl chloride; sodium carbonate in dichloromethane

1.5 h; Heating;

Kazemi; Kiasat; Javeherian

Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2005 , vol. 44, # 9 p. 1954 - 1956 Title/Abstract Full Text View citing articles Show Details

95%

With copper diacetate; acetonitrile

1.5 h; Reflux; Hide Experimental Procedure

Ma, Xiao-Yun; He, Ying; Lu, Ting-Ting; Lu, Ming

Tetrahedron, 2013 , vol. 69, # 12 p. 2560 - 2564 Title/Abstract Full Text View citing articles Show Details

4.2.3. 2-Chlorobenzonitrile (Table 2, entry 2)

To a 25 mL round-bottom flask equipped with magnetic stirrer were added 2-chlorobenzaldehyde oxime (311 mg, 2 mmol), cupric acetate (Cu(OAc)2) 36 mg (0.2 mmol) and acetonitrile(5 mL). The mixture was heated to reflux for 1.5 h. After cooling to room temperature, the solution was directly evaporated to dryness and the residue was purified by column chromatography on silica gel (ethyl acetate/n-hexane=1:10) to give 2chlorobenzonitrile as a white solid (261 mg, 95percent). 1H NMR (500 MHz, CDCl3): δ 7.39 (m, 1H), 7.56 (m, 2H), 7.69 (m, 1H) Data are in good agreement with the literature.24 94%

With triphenylphosphine; 2,3-dicyano-5,6-dichloro-pbenzoquinone in dichloromethane

T=20°C;

Aghapour, Ghasem; Amirabadi, Marjan

Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2007 , vol. 46, # 4 p. 649 - 652 Title/Abstract Full Text View citing articles Show Details

94%

With 1,1,3,3-tetraphenyl-2-oxa-1,3-phoshpinobenzene bis(trifluoromethanesulfonate); triethylamine in dichloromethane

T=20°C; 0.333333 h;

Moussa, Ziad

Synthesis, 2012 , vol. 44, # 3 art. no. T105811SS, p. 460 - 468 Title/Abstract Full Text View citing articles Show Details

94%

With thionyl chloride; captisol® in water; acetone

T=80°C; Beckmann Rearrangement; 0.25 h;

Patil, Dipak; Dalal, Dipak

Synthetic Communications, 2013 , vol. 43, # 1 p. 118 - 128 Title/Abstract Full Text View citing articles Show Details

93%

With 1,8-diazabicyclo[5.4.0]undec-7-ene; ptoluenesulfonyl imidazole in N,N-dimethyl-formamide

0.25 h; Reflux;

Rad, Mohammad Navid Soltani; Khalafi-Nezhad, Ali; Behrouz, Somayeh; Amini, Zohreh; Behrouz, Marzieh

Synthetic Communications, 2010 , vol. 40, # 16 p. 2429 - 2440 Title/Abstract Full Text View citing articles Show Details

93%

With trifluoromethylsulfonic anhydride; triethylamine; triphenylphosphine in dichloromethane

T=0°C; 0.166667 h;

Moussa, Ziad; Ahmed, Saleh A.; ElDouhaibi, Ahmad S.; Al-Raqa, Shaya Y.

Tetrahedron Letters, 2010 , vol. 51, # 14 p. 1826 - 1831 Title/Abstract Full Text View citing articles Show Details

92%

With N-chloro-succinimide; triphenylphosphine in dichloromethane

T=20°C;

Iranpoor; Firouzabadi; Aghapour

Synthetic Communications, 2002 , vol. 32, # 16 p. 2535 - 2541 Title/Abstract Full Text View citing articles Show Details

91%

With TiCl3(OTf); 1-n-butyl-3-methylimidazolim bromide

2 h;

Noei, Jalil; Khosropour, Ahmad Reza; Mirjafari, Arsalan

Bulletin of the Korean Chemical Society, 2012 , vol. 33, # 6 p. 2102 - 2104 Title/Abstract Full Text View citing articles Show Details

91%

With TCBDA; triphenylphosphine in dichloromethane

T=20°C; Reagent/catalyst; Hide Experimental Procedure

Ghorbani-Vaghei, Ramin; Shiri, Lotfi; Ghorbani-Choghamarani, Arash

Chinese Chemical Letters, 2013 , vol. 24, # 12 p. 1123 - 1126 Title/Abstract Full Text View citing articles Show Details

1:2 Experimental 2.1 Typical procedure for the conversion of 4-nitrobenzaldehyde oxime to 4-nitrobenzonitrile with TCBDA and PPh3

To a mixture of PPh3 (0.315 g, 1.2 mmol) and TCBDA (0.12 g, 0.32 mmol) in dichloromethane (5 mL), 4-nitrobenzaldehyde oxime (0.166 g, 1 mmol) was added. The mixture was stirred at room temperature. The progress of the reaction was monitored by TLC. After completion of the reaction (Table 1), the solvent was evaporated. The crude products were purified by short-column chromatography (packed with silica gel, using nhexane/ethyl acetate (8:2) as eluent) to achieve the desired 4-nitrobenzonitrile with 0.14 g, 95percent yield. 90%

With acetyl chloride; zinc(II) oxide

0.25 h; Heating;

Sarvari, Mona Hosseini

Synthesis, 2005 , # 5 art. no. Z18204SS, p. 787 - 790 Title/Abstract Full Text View citing articles Show Details

90%

With 8-bromocaffeine; 1,8-diazabicyclo[5.4.0]undec-7ene in N,N-dimethyl-formamide

0.0305556 h; Microwave irradiation; chemoselective reaction;

Soltani Rad, Mohammad Navid; Behrouz, Somayeh; Nekoei, Abdo-Reza

Synlett, 2012 , vol. 23, # 8 p. 1191 - 1198 Title/Abstract Full Text View citing articles Show Details

90%

With acetonitrile

4 h; RefluxGreen chemistry;

Zarghani, Monireh; Akhlaghinia, Batool

Applied Organometallic Chemistry, 2015 , vol. 29, # 10 p. 683 - 689 Title/Abstract Full Text View citing articles Show Details

90%

With C H ClF N Os in acetonitrile

Francos, Javier; González-Liste, Pedro J.; Menéndez-Rodríguez, Lucía; Crochet, Pascale; Cadierno, Victorio; Borge, Javier; Antiñolo, Antonio; Fernández-Galán, Rafael; Carrillo-Hermosilla, Fernando

24 33

3 3

T=80°C; 1 h; Sealed tube;

European Journal of Inorganic Chemistry, 2016 , vol. 2016, # 3 p. 393 - 402 Title/Abstract Full Text View citing articles Show Details

89%

With C8H14N2O4S in dichloromethane

1 h; Reflux;

Rappai, John P.; Karthikeyan, Jayakumar; Prathapan, Sreedharan; Unnikrishnan, Perupparampil A.

Synthetic Communications, 2011 , vol. 41, # 17 p. 2601 - 2606 Title/Abstract Full Text View citing articles Show Details

89%

With acetic anhydride; potassium carbonate in dimethyl sulfoxide

T=50°C; 12 h; Hide Experimental Procedure

Song, Yaoping; Shen, Dongguo; Zhang, Qinghua; Chen, Bo; Xu, Guangyu

Tetrahedron Letters, 2014 , vol. 55, # 3 p. 639 - 641 Title/Abstract Full Text View citing articles Show Details

A general procedure for the preparation of nitrile from aldoxime using aceticanhydride as the dehydration agent

General procedure: K2CO3 (3 mmol) was added to a stirredmixture of aldoxime (1.5 mmol) and 6 mL DMSO, followed by Ac2O (3 mmol).The resulting mixture was stirred at 50 C for a specified period (Table 2). Afterthe reaction was completed, 30 mL water was added then extracted withCH2Cl2 (10 3 mL). The organic phase was washed with water (10 3 mL)then dried with anhydrous Na2SO4. The solvent was evaporated under vacuumto give the nitrile products. 86%

With MIL-100 (Fe)-NH4F in o-xylene

T=153 - 160°C; 2.5 h; Dean-StarkInert atmosphere;

Rapeyko, Anastasia; Climent, Maria J.; Corma, Avelino; Concepciõn, Patricia; Iborra, Sara

ChemSusChem, 2015 , vol. 8, # 19 p. 3270 - 3282 Title/Abstract Full Text View citing articles Show Details

85%

With 1,4-diaza-bicyclo[2.2.2]octane; thionyl chloride in dichloromethane

T=20°C; 1.16667 h;

Kazemi; Kiasat

Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2003 , vol. 42, # 6 p. 1540 - 1543 Title/Abstract Full Text View citing articles Show Details

85%

With poly(ethylene glycol)–bound sulfonyl chloride in dichloromethane

1.16667 h; Reflux; Hide Experimental Procedure

Zhang, Xiao-Lan; Liu, Xiao-Ling; Sang, Xiao-Yan; Sheng, Shou-Ri

Synthetic Communications, 2017 , vol. 47, # 3 p. 232 - 237 Title/Abstract Full Text View citing articles Show Details

General procedure for the preparation of nitriles

General procedure: PEG-SO2Cl (0.15 mmol, 326 mg) was added to a stirred solution of aldoxime (1.0 mmol) in freshly distilled dichloromethane (10 mL), and the reaction mixture stirred at reflux temperature for the given time in Table 2. After completion of the reaction (monitored by TLC), the solution was concentrated by rotary evaporation and diluted with slow addition of an excess of cold ether with vigorous stirring. The precipitate was filtered through a fritted funnel, washed with ether, and dried well to furnish the PEG-bound sulfonic acid in excellent yield and then converted into the PEG-SO2Cl for the recycling. The filtrate was concentrated in a rotary evaporator, and finally the crude product was purified by column chromatography eluted with 10–20percent ethyl acetate in hexane for their structure analysis. 84%

With Montmorillonite KSF in toluene

14 h; Heating;

Meshram

Synthesis, 1992 , # 10 p. 943 - 944 Title/Abstract Full Text View citing articles Show Details

84%

With Polyethylene glycol supported phosphorus chloride in dichloromethane

0.666667 h; RefluxMolecular sieve; Hide Experimental Procedure

Zhang, Xiao-Lan; Sheng, Shou-Ri; Wei, Mei-Hong; Liu, Xiao-Ling

Phosphorus, Sulfur and Silicon and the Related Elements, 2017 , vol. 192, # 5 p. 513 - 517 Title/Abstract Full Text View citing articles Show Details

Preparation of nitriles (4a–4r): General procedure

General procedure: To a stirred solution of aldoxime 3 (1.0 mmol) in CH2Cl2 (5 mL)was added PEG-OPCl2 (0.20 mmol, 220 mg) and molecularsieves 4 A (2 wt equiv to aldoxime), the reaction mixture stirred at reuxing temperature for the given time in Table 2. Aftercompletion of the reaction (TLC), diethyl ether (100 mL) wasadded to the reaction mixture with vigorous stirring and thencooled to 0 °C. The recovered white precipitate, along withmolecular sieves 4 A was collected by fltration, washed with cold diethyl ether (2 × 20 mL) for reuse. The combined fltratewas concentrated in a rotary evaporator, and the residue waspurifed by through a pad of silica gel column (10-20percent ethylacetate in hexane) to give pure product, which was characterized by comparison of its IR and 1H NMR spectra or meltingpoint with published13,14,16,18,26,28,30 values. The analytical datafor the obtained products 4a–4r are together with their 1H and13C NMR spectra are presented in the Supplemental Materials(Figures S1– S36). 80%

With aluminum oxide

0.05 h; microwave irradiation;

Lingaiah, Nagarapu; Narender, Ravirala

Synthetic Communications, 2002 , vol. 32, # 15 p. 2391 - 2394 Title/Abstract Full Text View citing articles Show Details

80%

With CTADC in dichloromethane

4 h; Heating;

Sahu, Sandhyamayee; Patel, Sabita; Mishra, Bijay K.

Synthetic Communications, 2005 , vol. 35, # 24 p. 3123 - 3126 Title/Abstract Full Text View citing articles Show Details

78%

With 1,2-bis(3-fluorophenyl)diselane; dihydrogen peroxide in acetonitrile

T=65°C; 24 h;

Yu, Lei; Li, Hongyan; Zhang, Xu; Ye, Jianqing; Liu, Jianping; Xu, Qing; Lautens, Mark

Organic Letters, 2014 , vol. 16, # 5 p. 1346 - 1349 Title/Abstract Full Text View citing articles Show Details

70%

With carbon disulfide; sodium hydroxide; tetra(nbutyl)ammonium hydrogensulfate in benzene

0.5 h; Ambient temperature;

Shinozaki, Hiraku; Imaizumi, Mari; Tajima, Moritaka

Chemistry Letters, 1983 , p. 929 - 932 Title/Abstract Full Text Show Details

70%

With iron(III) sulfate in benzene

Dehydration; 3.5 h; Heating;

Desai; Swami; Mahale

Synthetic Communications, 2000 , vol. 30, # 9 p. 1623 - 1625 Title/Abstract Full Text View citing articles Show Details

27%

With diethyl chlorophosphate in toluene

Beckmann rearrangement; 3 h; Heating;

Sardarian; Shahsavari-Fard; Shahsavari; Ebrahimi

Tetrahedron Letters, 2007 , vol. 48, # 14 p. 2639 - 2643 Title/Abstract Full Text View citing articles Show Details

With 2-(trifluoroacetyloxy)pyridine in tetrahydrofuran

Heating; Yield given;

Keumi, Takashi; Shimada, Masakazu; Morita, Toshio; Kitajima, Hidehiko

Bulletin of the Chemical Society of Japan, 1990 , vol. 63, # 8 p. 2252 - 2256 Title/Abstract Full Text Show Details

With 1-[(4-chlorosulfonyl)butyl]-3-methylimidazolium chlorosulfate in acetonitrile

T=100°C; 3 h;

Nakajima, Mizuki; Qiao, Kun; Kobayashi, Nobuhisa; Bao, Quanxi; Tomida, Daisuke; Yokoyama, Chiaki

Chemistry Letters, 2011 , vol. 40, # 4 p. 396 - 397 Title/Abstract Full Text View citing articles Show Details

With acetic anhydride

Reflux;

Li, Ziyuan; Ma, Ling; Xu, Jinyi; Kong, Lingyi; Wu, Xiaoming; Yao, Hequan

Chemical Communications, 2012 , vol. 48, # 31 p. 3763 - 3765 Title/Abstract Full Text View citing articles Show Details

With phosphorus pentoxide

2 h; Reflux;

Khan, Khalid Mohammed; Fatima, Itrat; Saad, Syed Muhammad; Taha, Muhammad; Voelter, Wolfgang

Tetrahedron Letters, 2016 , vol. 57, # 5 p. 523 - 524 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar 96%

With copper(II) oxide; hydroxylamine hydrochloride in neat (no solvent) 0.0208333 h; Microwave irradiationGreen chemistry; Mechanism; Reagent/catalyst; Hide Experimental Procedure

Synthesize Find similar

Rx-ID: 2408593 Find similar reactions

Anandakumar, Belladamadu Siddappa; Reddy, Muthukur Bhojegowd Madhusudana; Tharamani, Chikka Nagaiah; Pasha, Mohamed Afzal; Chandrappa, Gujjarahalli Thimmanna

Chinese Journal of Catalysis, 2013 , vol. 34, # 4 p. 704 - 710 Title/Abstract Full Text Show Details

2.3. General procedure

General procedure: A mixture of aldehyde (2 mmol), hydroxylamine hydrochloride (3 mmol), and copper oxide NPs (5 molpercent) was placed in a Pyrex cylindrical tube and then homogenized and irradiated at 250 W in a MILESTONE microwave reactor. After irradiation (1-2 min), the mixture was cooled to 25 °C and extracted with dichloromethane (5 ml x 2). The solvent was filtered under vacuum and the organic layer dried over fused calcium chloride. The crude product was then subjected to short-column silica gel chromatography using light petrol as an eluent to produce pure product. 95%

With PhNHCO2NH2*TsOH in toluene

Condensation; elimination; 0.5 h; Heating;

Coskun, Necdet; Arikan, Nevin

Tetrahedron, 1999 , vol. 55, # 40 p. 11943 - 11948 Title/Abstract Full Text View citing articles Show Details

94%

With hexamethylene bis(Nmethylimidazolium)bis(dichloroiodate); ammonia in water; acetonitrile

T=20°C; 0.833333 h; Hide Experimental Procedure

Hosseinzadeh, Rahman; Golchoubian, Hamid; Nouzarian, Mahboobe

Research on Chemical Intermediates, 2015 , vol. 41, # 7 p. 4713 - 4725 Title/Abstract Full Text View citing articles Show Details

General procedure for the conversion of aldehydes into nitriles with HMBMIBDCI and NH3(aq)

General procedure: The mixture of HMBMIBDCI (0.5 mmol, 322 mg) in CH3CN (5 ml) was added into a solution of p-chlorobenzaldehyde (0.5 mmol, 70 mg) in NH3(aq) (1.5 ml) and the resulting dark mixture was stirred for the specified time designated in Table 2 at room temperature. The progress of the reaction was followed by TLC and the dark heterogeneous solution gradually changed to a red solution. To the mixture was added CHCl3 (30 ml) and then the organic phase was washed with an aqueous solution of NaHSO3 (5percent, 20 ml). The organic layer was dried over MgSO4 and evaporated under reduced pressure. The crude material obtained was practically pure in most cases with no need for further purification. Otherwise, the crude products were purified by recrystallization or preparative TLC. All the nitrile products were identified by comparing melting point, 1H, and 13C NMR with those of authentic samples reported in the literature. 2-Chlorobenzonitrile (Table 2, entry 11). Mp 41–43 °C [Ref. [16] mp 42–44 °C]; 1H NMR (400 MHz, CDCl3): δ (ppm) = 7.70 (ddd, J = 7.6, 1.6, 0.4 Hz, 1 H), 7.60–7.53 (m, 2 H), 7.40 (ddd,J = 6.4, 1.6, 0.8 Hz, 1 H). 13C NMR (100 MHz, CDCl3): δ (ppm) = 136.92, 134.04, 133.87, 130.07, 127.14, 115.98, 113.45.

93%

With hydroxylamine hydrochloride; methanesulfonyl chloride in neat (no solvent) T=70°C; 1.5 h;

Khalafi-Nezhad, Ali; Mohammadi, Somayeh

RSC Advances, 2014 , vol. 4, # 27 p. 13782 - 13787 Title/Abstract Full Text View citing articles Show Details

93%

With ammonium acetate; phenyltrimethylammonium tribromide in acetonitrile

T=20°C; 64 h; Hide Experimental Procedure

Sayama, Shinsei

Heterocycles, 2016 , vol. 92, # 10 p. 1796 - 1802 Title/Abstract Full Text View citing articles Show Details

General procedure: to a solution of 2-pyridinecarbaldehyde 1 (54 mg, 0.5 mmol) and ammonium acetate (385mg, 5.0 mmol) in MeCN )6ml), was added trimethylphenylammonium tribromide (376 mg, 1.0 mmol) at room temperature. after stirring for 21 h at rt, the reaction mixture was treated with 0.5 M aq Na2S2O3(10 ml), 1.0 M NaHCO3 )15 ml) and extracted with EtOAc (60 mL). The organic layer was washed with 0.5 M Na2S2O3 and successively washed with saturated aq.NaCl, and dried over MgSO4. 92%

With hydroxylamine hydrochloride; toluene-4-sulfonic acid

0.00972222 h; Microwave irradiation;

Reddy, M. B. Madhusudana; Pasha

Synthetic Communications, 2010 , vol. 40, # 22 p. 3384 - 3389 Title/Abstract Full Text View citing articles Show Details

92%

With tert.-butylhydroperoxide; ammonium acetate; iodine; sodium carbonate in ethanol

T=50°C; 4.5 h; Green chemistry;

Fang, Chaojie; Li, Meichao; Hu, Xinquan; Mo, Weimin; Hu, Baoxiang; Sun, Nan; Jin, Liqun; Shen, Zhenlu

RSC Advances, 2017 , vol. 7, # 3 p. 1484 - 1489 Title/Abstract Full Text View citing articles Show Details

92%

With tert.-butylhydroperoxide; ammonium acetate; iodine; sodium carbonate in ethanol

T=50°C; 4.5 h; Hide Experimental Procedure

Zhejiang University of Technology; Shen Zhenlu; Li Meichao; Fang Chaojie; Mo Weimin

Patent: CN106748881 A, 2017 ; Location in patent: Paragraph 0034 ; Title/Abstract Full Text Show Details

17:Example 17: Preparation of o-chlorobenzonitrile (Formula (2-3))

To a 25 mL two-necked round bottom flask equipped with a thermometer and a magnetic stirrer was added 4 mmol of o-chlorobenzaldehyde (Formula (1-3), 6 mmol of NH4OAc, 4 mmol of Na2CO3, 4.4 mmol of TBHP, 0.1 mmol of an I2, 5 mL of absolute ethanol solvent, The reaction flask was then placed in an oil bath which was previously heated to 50 ° C and opened with a magnetic stirrer for 4.5 h. The reaction solution was added The sodium thiosulfate solution is stirred, then extracted with ether, the organic layer is separated, the solvent is distilled off under reduced pressure, and then subjected to column chromatography, The eluent was taken as the eluent with ethyl acetate / petroleum ether volume ratio of 1: 100 as the eluent, and the eluate containing the target compound was collected. To obtain o-chlorobenzonitrile, the separation yield of 92percent. 91%

With ammonium acetate; iodine

T=70°C; 0.5 h;

Ren, Yi-Ming; Zhu, Yi-Zhong; Cai, Chun

Journal of Chemical Research, 2008 , # 1 p. 18 - 19 Title/Abstract Full Text View citing articles Show Details

91%

Stage #1: With ammonia in water

T=20°C; 0.166667 h; Stage #2: With tetra-N-butylammonium tribromide in water

T=20°C; 4 h;

Zhu, Yi-Zhong; Cai, Chun

Monatshefte fur Chemie, 2010 , vol. 141, # 6 p. 637 - 639 Title/Abstract Full Text View citing articles Show Details

91%

With potassium hexafluorophosphate; 2,2,6,6Tetramethyl-1-piperidinyloxy free radical; oxygen; 1,1,1,3,3,3-hexamethyldisilazane; sodium nitrite in acetic acid; acetonitrile

T=30°C; 4 h; Sealed tube;

Fang, Chaojie; Li, Meichao; Hu, Xinquan; Mo, Weimin; Hu, Baoxiang; Sun, Nan; Jin, Liqun; Shen, Zhenlu

Advanced Synthesis and Catalysis, 2016 , vol. 358, # 7 p. 1157 - 1163 Title/Abstract Full Text View citing articles Show Details

91%

With ammonium hydroxide; dihydrogen peroxide

T=100°C; 4 h; Green chemistry;

Bhardwaj, Madhvi; Kour, Manmeet; Paul, Satya

RSC Advances, 2016 , vol. 6, # 101 p. 99604 - 99614 Title/Abstract Full Text View citing articles Show Details

90%

With potassium hydroxide; ammonium bicarbonate; (Bu4N)2S2O8; copper(I) formate; nikel(II) formate in acetonitrile

T=20°C; Condensation; Oxidation; 2 h;

Chen; Fu; Meng; Cheng; Lu

Synthesis, 2000 , # 11 p. 1519 - 1520 Title/Abstract Full Text View citing articles Show Details

90%

With aluminum oxide; hydroxylamine hydrochloride; methanesulfonyl chloride

T=100°C; 0.666667 h;

Sharghi, Hashem; Sarvari, Mona Hosseini

Tetrahedron, 2002 , vol. 58, # 52 p. 10323 - 10328 Title/Abstract Full Text View citing articles Show Details

90%

With hydroxylamine hydrochloride; zinc(II) chloride

Paesha; Nizam, Aatika

0.00777778 h; Microwave irradiationNeat (no solvent);

Synthetic Communications, 2010 , vol. 40, # 9 p. 1276 - 1279 Title/Abstract Full Text View citing articles Show Details

90%

With hydroxylamine hydrochloride; zinc(II) oxide

0.00972222 h; Microwave irradiationneat (no solvent);

Madhusudana Reddy; Pasha

Chinese Chemical Letters, 2010 , vol. 21, # 9 p. 1025 - 1028 Title/Abstract Full Text View citing articles Show Details

90%

With hydroxylamine hydrochloride; iron(II) sulfate in N,N-dimethyl-formamide

2.5 h; Reflux;

Patil, Dinanath D.; Wadhava, Gurumeet C.; Deshmukh, Arun K.

Asian Journal of Chemistry, 2012 , vol. 24, # 3 p. 1401 - 1402 Title/Abstract Full Text View citing articles Show Details

89%

Stage #1: With ammonium hydroxide; potassium iodide in tetrahydrofuran

T=20°C; 0.166667 h; Stage #2: With chloroamine-T in tetrahydrofuran

T=20°C; 4 h;

Zhu, Yi-Zhong; Zhang, Xi-Quan; Liu, Fei; Gu, Hong-Mei; Zhu, Hai-Liang

Synthetic Communications, 2013 , vol. 43, # 21 p. 2943 - 2948 Title/Abstract Full Text View citing articles Show Details

88%

With ammonia; sodium methylate; potassium iodide in methanol

T=5°C; electrooxidation;

Okimoto, Mitsuhiro; Chiba, Toshiro

Journal of Organic Chemistry, 1988 , vol. 53, # 1 p. 218 - 219 Title/Abstract Full Text View citing articles Show Details

88%

With Envirocat EPZGR; hydroxylamine hydrochloride; triethylamine

Reduction; 0.05 h; Irradiation;

Veverkova, Eva; Toma, Stefan

Synthetic Communications, 2000 , vol. 30, # 17 p. 3109 - 3114 Title/Abstract Full Text View citing articles Show Details

88%

With hydroxylamine hydrochloride; sodium acetate; acetonitrile; copper(II) oxide

10 h; Reflux; Hide Experimental Procedure

Ma, Xiaoyun; Ao, Jun; Chen, Zhengjian; Liu, Yi

Journal of Chemical Research, 2017 , vol. 41, # 8 p. 465 - 468 Title/Abstract Full Text Show Details

Synthesis of nitriles; general procedure

General procedure: An aldehyde (2 mmol), CuO (0.1 mmol), NH2OH·HCl (3 mmol),NaOAc (3 mmol) and acetonitrile (6 mL) were added to a 25 mL round bottom flask equipped with magnetic stirrer. The mixture was heated to reflux for 3–10 h. After cooling to r.t., acetonitrile was distilled off under reduced pressure. Water (15 mL) and ethyl acetate (30 mL) were added to the reaction mixture, and the organic layer was washed with saturated aqueous sodium bicarbonate (1 × 15 mL) and water(1 × 15 mL). The organic layer was dried with Na2SO4, evaporated and the residue was purified by column chromatography on silica gel (ethylacetate/n-hexane) to give the corresponding nitriles. All the nitriles are commercially available and were characterised by 1H NMR spectra,which are available in the ESI. 86%

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium perchlorate; acetic acid; lithium hexamethyldisilazane in acetonitrile

12 h; Electrochemical reaction; Hide Experimental Procedure

Chen, Qiguo; Fang, Chaojie; Shen, Zhenlu; Li, Meichao

Electrochemistry Communications, 2016 , vol. 64, p. 51 - 55 Title/Abstract Full Text View citing articles Show Details

General procedure: Preparative electrolysis experiments were performed using 263 APotentiostat/Galvanostat (Princeton Applied Research, USA). 0.1 MNaClO4–CH3CN solution (10 mL) containing aldehydes (1 mmol),TEMPO (0.1 mmol), HMDS (2.5mmol) and AcOH (2.5mmol) was electrolyzedwith stirring in an undivided cell (30 mL) equipped with twoplatinum sheets as anode (1.5 cm2) and cathode (3.0 cm2) respectivelyat a constant potential of 1.5 V vs Ag/Ag+ (0.1MAgNO3 in acetonitrile).The electrode separation was 1 cm. When the reaction was finished,10mL of saturatedNa2SO3 solution was added into the reactionmixtureand stirred for 15 min. Then the mixture was extracted with CH2Cl2(20 mL × 3). The organic layer was dried with anhydrous Na2SO4 andconcentrated in a rotary evaporator. The productswere obtained via purificationof column chromatography and their structures were confirmedby 1H NMR, 13C NMR and MS. NMR was performed on a BrukerAvance III spectrometer. GC-MS was performed on the Thermo TraceISQ instrument with TG 5MS capillary column. 84%

With 4-acetylamino-2,2,6,6-tetramethyl-1piperidinoxy; ammonium acetate; sodium perchlorate in acetonitrile

T=20°C; Electrolysis;

Yang, Xianjing; Fan, Zhongquan; Shen, Zhenlu; Li, Meichao

Electrochimica Acta, 2017 , vol. 226, p. 53 - 59 Title/Abstract Full Text View citing articles Show Details

82%

With boron trifluoride diethyl etherate; O-(2aminobenzoyl) hydroxylamine in ethanol

4 h; Heating;

Reddy, P.S.N.; Reddy, P.Pratar

Synthetic Communications, 1988 , vol. 18, # l6-17 p. 2179 - 2182 Title/Abstract Full Text Show Details

82%

With tert.-butylhydroperoxide; ammonium hydroxide; tetra-(n-butyl)ammonium iodide in water

T=80°C; 12 h; Catalytic behavior;

Wang, Liang; Shen, Chen; Wang, Hai-Ping; Zhou, Wei-You; Sun, Fu-An; He, Ming-Yang; Chen, Qun

Journal of Chemical Research, 2012 , vol. 36, # 8 p. 460 - 462 Title/Abstract Full Text View citing articles Show Details

80%

With hydroxylamine hydrochloride; iodine in dimethyl sulfoxide

T=20°C;

Gaikwad, Digambar D.; Renukdas, Sameer V.; Kendre, Babasaheb V.; Shisodia, Suresh U.; Borade, Ravikumar M.; Shinde, Praveen S.; Chaudhary, Sunil S.; Pawar, Rajendra P.

Synthetic Communications, 2007 , vol. 37, # 2 p. 257 - 259 Title/Abstract Full Text View citing articles Show Details

80%

With pyridine; hydroxylamine hydrochloride

Pasha; Nizam, Aatika

0.0111111 h; Microwave irradiationneat (no solvent);

Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2010 , vol. 49, # 8 p. 1127 - 1129 Title/Abstract Full Text View citing articles Show Details

78%

With oxygen; acetonitrile; copper(l) chloride in N,Ndimethyl acetamide

T=130°C; 24 h; Schlenk technique;

Liu, Lixin; Dong, Jianyu; Zhang, Yaxing; Zhou, Yongbo; Yin, Shuang-Feng

Organic and Biomolecular Chemistry, 2015 , vol. 13, # 39 p. 9948 - 9952 Title/Abstract Full Text View citing articles Show Details

70%

With phosphorus pentaoxide; phosphoric acid; hydroxylamine hydrochloride in acetic acid

0.25 h; Heating;

Ganboa, I.; Palomo, C.

Synthetic Communications, 1983 , vol. 13, # 12 p. 999 - 1006 Title/Abstract Full Text Show Details

70%

With pyridine; hydroxylamine hydrochloride; formamide in xylene

Condensation; 6 h; Heating;

Ali, Sayyed Iliyas; Nikalje, Milind D.; Dewkar, Gajanan K.; Paraskar, Abhimanyu S.; Jagtap; Sudalai

Journal of Chemical Research - Part S, 2000 , # 1 p. 30 - 31 Title/Abstract Full Text View citing articles Show Details

25%

With ammonia; aluminum oxide; copper

T=320°C;

Card, Roger J.; Schmitt, J. Lawrence

Journal of Organic Chemistry, 1981 , vol. 46, p. 754 - 757 Title/Abstract Full Text View citing articles Show Details

Multi-step reaction with 2 steps 1: NH2OH*HCl; ZnO / Heating 2: 90 percent / CH3COCl; ZnO / 0.25 h / Heating View Scheme

Sarvari, Mona Hosseini

Synthesis, 2005 , # 5 art. no. Z18204SS, p. 787 - 790 Title/Abstract Full Text View citing articles Show Details

Multi-step reaction with 2 steps 1: water; NH2Cl / 0 °C 2: 275 °C View Scheme

Hauser; Hauser

Journal of the American Chemical Society, 1930 , vol. 52, p. 2050,2052 Full Text View citing articles Show Details

Multi-step reaction with 2 steps 1: water; NH2Cl / 0 °C 2: 30 °C / Aufbewahren im Exsiccator ueber NaOH View Scheme

Hauser; Hauser; Gillaspie

Journal of the American Chemical Society, 1930 , vol. 52, p. 4158,4161 Full Text View citing articles Show Details

Multi-step reaction with 2 steps 1: hydroxylamine hydrochloride; sodium carbonate / methanol; water / Reflux 2: acetic anhydride / Reflux View Scheme

Li, Ziyuan; Ma, Ling; Xu, Jinyi; Kong, Lingyi; Wu, Xiaoming; Yao, Hequan

Chemical Communications, 2012 , vol. 48, # 31 p. 3763 - 3765 Title/Abstract Full Text View citing articles Show Details

Multi-step reaction with 2 steps 1: hydroxylamine hydrochloride; sodium acetate / water; methanol 2: acetic anhydride; potassium carbonate / dimethyl sulfoxide / 12 h / 50 °C View Scheme

Song, Yaoping; Shen, Dongguo; Zhang, Qinghua; Chen, Bo; Xu, Guangyu

Tetrahedron Letters, 2014 , vol. 55, # 3 p. 639 - 641 Title/Abstract Full Text View citing articles Show Details

Multi-step reaction with 3 steps 1: ammonia / water / 20 °C / |Green chemistry 2: iodine / water / 20 °C / |Green chemistry 3: ammonia / water / 20 °C / |Green chemistry View Scheme

Yadav, Arvind K.; Srivastava, Vishnu P.; Yadav, Lal Dhar S.

Synthetic Communications, 2014 , vol. 44, # 3 p. 408 - 416 Title/Abstract Full Text View citing articles Show Details

Multi-step reaction with 2 steps 1: hydroxylamine hydrochloride / N,N-dimethyl-formamide / 3 h / |Reflux 2: phosphorus pentoxide / 2 h / |Reflux View Scheme

Khan, Khalid Mohammed; Fatima, Itrat; Saad, Syed Muhammad; Taha, Muhammad; Voelter, Wolfgang

Tetrahedron Letters, 2016 , vol. 57, # 5 p. 523 - 524 Title/Abstract Full Text View citing articles Show Details

Multi-step reaction with 2 steps 1: hydroxylamine hydrochloride 2: poly(ethylene glycol)–bound sulfonyl chloride / dichloromethane / 1.17 h / |Reflux View Scheme

Zhang, Xiao-Lan; Liu, Xiao-Ling; Sang, Xiao-Yan; Sheng, Shou-Ri

Synthetic Communications, 2017 , vol. 47, # 3 p. 232 - 237 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 4207953 Find similar reactions

98%

With pyridine; Oxonereg;; 4-acetylamino-2,2,6,6tetramethyl-1-piperidinoxy; Pyridine hydrobromide in dichloromethane

T=20°C; 12 h; Green chemistry;

Lambert, Kyle M.; Bobbitt, James M.; Eldirany, Sherif A.; Kissane, Liam E.; Sheridan, Rose K.; Stempel, Zachary D.; Sternberg, Francis H.; Bailey, William F.

Chemistry - A European Journal, 2016 , vol. 22, # 15 p. 5156 - 5159 Title/Abstract Full Text View citing articles Show Details

90%

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; free radical; trichloroisocyanuric acid in dichloromethane

T=10°C; 2 h;

Chen, Fen-Er; Kuang, Yun-Yan; Dai, Hui-Fang; Lu, Liang; Huo, Ming

Synthesis, 2003 , # 17 p. 2629 - 2631 Title/Abstract Full Text View citing articles Show Details

90%

With pyridine; [Pip*(O)][BF4] in dichloromethane

T=20°C; 12 h; Inert atmosphere;

Lambert, Kyle M.; Bobbitt, James M.; Eldirany, Sherif A.; Wiberg, Kenneth B.; Bailey, William F.

Organic Letters, 2014 , vol. 16, # 24 p. 6484 - 6487 Title/Abstract Full Text View citing articles Show Details

87%

With ammonium hydroxide; iodine

T=60°C; 2 h;

Iida, Shinpei; Togo, Hideo

Tetrahedron, 2007 , vol. 63, # 34 p. 8274 - 8281 Title/Abstract Full Text View citing articles Show Details

87%

With ammonium hydroxide; iodine

T=60°C; 2 h;

Iida, Shinpei; Togo, Hideo

Synlett, 2006 , # 16 p. 2633 - 2635 Title/Abstract Full Text View citing articles Show Details

82%

With copper(l) iodide; oxygen in dichloromethane

T=20°C; P=760.051 Torr; 2 h; Sealed tube;

Xu, Boran; Hartigan, Elizabeth M.; Feula, Giancarlo; Huang, Zheng; Lumb, Jean-Philip; Arndtsen, Bruce A.

Angewandte Chemie - International Edition, 2016 , vol. 55, # 51 p. 15802 - 15806 Angew. Chem., 2016 , vol. 128, p. 16034 - 16038,5 Title/Abstract Full Text View citing articles Show Details

75%

With cis-[Os(VIII)O4(OH)2](2-); [Fe(CN)6](3); acetonitrile

T=20°C; 1.5 h;

Griffith; Suriaatmaja

Canadian Journal of Chemistry, 2001 , vol. 79, # 5-6 p. 598 - 606 Title/Abstract Full Text View citing articles Show Details

74%

With pyridine; tert.butylhydroperoxide; iodine; potassium carbonate in water

T=80°C; 0.1 h;

Zhang, Jintang; Wang, Zhentao; Wang, Ye; Wan, Changfeng; Zheng, Xiaoqi; Wang, Zhiyong

Green Chemistry, 2009 , vol. 11, # 12 p. 1973 - 1978 Title/Abstract Full Text View citing articles Show Details

72%

With ammonium hydroxide; 1,3-Diiodo-5,5-dimethyl-2,4imidazolidinedione

T=60°C; 3 h;

Iida, Shinpei; Togo, Hideo

Synlett, 2007 , # 3 p. 407 - 410 Title/Abstract Full Text View citing articles Show Details

70%

With potassium hydroxide; dipotassium peroxodisulfate; ruthenium trichloride in water

1 h;

Griffith, William P.; Reddy, Bharti; Shoair, Abdel G. F.; Suriaatmaja, Maria; White, Andrew J. P.; Williams, David J.

Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999), 1998 , # 7 p. 2819 - 2826 Title/Abstract Full Text Show Details

61.5%

With 5 active carbon-supported ruthenium; oxygen in toluene

T=150°C; P=3750.38 Torr; 4 h; Autoclave; Hide Experimental Procedure

Niu, Baoqiang; Lu, Fei; Zhang, Hong-Yu; Zhang, Yuecheng; Zhao, Jiquan

Chemistry Letters, 2017 , vol. 46, # 3 p. 330 - 333 Title/Abstract Full Text View citing articles Show Details

General procedure: In a typical process, into a 25 ml autoclave equipped with a magnetic stirrer were added 5percentRu/AC (0.03 mmol, 3 molpercent), benzylamine (1 mmol), 5 mL toluene at room temperature successively. After which the resulting reaction mixture was heated at 150 °C for 4 h under 0.5 MPa of oxygen atmosphere. The final reaction conversion and selectivity towards the corresponding nitriles were determined by Gas Chromatograph. After reaction, the product was purified by column chromatography of the reaction mixture on neutral alumina using hexanes/dichloromethane (80:20) or hexanes/EtOAc (30:1) as eluent. 17%

With HRu(1,3-bis(6'-methyl-2'-pyridylimino)isoindoline) (PPh3)2 in toluene

T=110°C; 24 h; Inert atmosphereGlovebox; chemoselective reaction;

Tseng, Kuei-Nin T.; Rizzi, Andrew M.; Szymczak, Nathaniel K.

Journal of the American Chemical Society, 2013 , vol. 135, # 44 p. 16352 - 16355 Title/Abstract Full Text View citing articles Show Details

76 % Spectr.

With iodine; tert-butylamine in acetonitrile

6 h; Ambient temperature;

Goosen, Andre; McCleland, Cedric W.; Sipamia, Allworth M.

Journal of Chemical Research, Miniprint, 1995 , # 1 p. 311 - 332 Title/Abstract Full Text Show Details

78 % Chromat.

With 3 A molecular sieve; oxygen; copper dichloride in toluene

T=80°C; P=760 Torr; 12 h;

Maeda, Yasunari; Nishimura, Takahiro; Uemura, Sakae

Bulletin of the Chemical Society of Japan, 2003 , vol. 76, # 12 p. 2399 - 2403 Title/Abstract Full Text View citing articles Show Details

99 % Chromat.

With oxygen; RuHAP in toluene

T=110°C; 12 h;

Mori; Yamaguchi; Mizugaki; Ebitani; Kaneda

Chemical Communications, 2001 , # 5 p. 461 - 462 Title/Abstract Full Text View citing articles Show Details

With 2-hydroperoxypropane in 1,4-dioxane

T=30°C; P=760.051 Torr; 3 h; Hide Experimental Procedure

Dalian Institute of Chemical Physics; Wang, Feng; Zhang, Zhe; Xu, Jie; Wang, Min; Zhang, Chaofeng; Chen, Haijun

Patent: CN105085315 B, 2017 ; Location in patent: Paragraph 0034; 0035 ; Title/Abstract Full Text Show Details

5:Example 5

0.5 ml of o-chlorobenzylamine, 0.05 g of CoAPO-3, 2 ml of 1,4-dioxane was added to a pressure-resistant flask,Mmol of isopropyl hydroperoxide at 30 ° C under normal pressure for 3 hours. The reaction product was analyzed by GC-MS. The amine conversionTo 57percent, nitrile, i.e., o-chlorobenzonitrile, was 93percent selectivity.

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With 20 V2O5/Al2O3; ammonia

T=350°C; P=760.051 Torr; Temperature; Hide Experimental Procedure

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Rx-ID: 5143583 Find similar reactions

Dwivedi, Ritambhara; Sharma, Prabhakar; Sisodiya, Akrati; Batra, Manohar Singh; Prasad, Rajendra

Journal of Catalysis, 2017 , vol. 345, p. 245 - 257 Title/Abstract Full Text View citing articles Show Details

2.3. Catalytic activity

The activity of the catalysts for vapor-phase ammoxidation of 2-CLT to 2-CLBN was carried out at atmospheric pressure in a fixedbed,vertical downflow glass reactor placed inside a tubular furnace.The temperature was regulated with the help of energy regulatorsand metered by a thermocouple inserted in the reactor.Fresh catalyst (1.0 g) was charged into the center of the reactorin such a way that the catalyst was sandwiched between two layersof inert glass beads. The reactant 2-chlorotoluene (2-CLT) wasfed using a pressure-equalizing funnel. Air and NH3 were taken from compressed gas cylinders. The flow rates of these gases weremeasured using a manometer. Experiments were carried out in thetemperature range 350–450 C. Reaction products were cooledthrough an ice-cooled condenser and collected in an ice-cooledreceiver. Product analysis was carried out with the help of a gaschromatograph filled with a flame ionization detector and a capillarycolumn. With ammonia; oxygen; DC-108 T=425°C; Yield given;

Qiong, Zheng; Chi, Huang; Guangyong, Xie; Chongwen, Xu; Yuanyin, Chen

Synthetic Communications, 1999 , vol. 29, # 13 p. 2349 - 2354 Title/Abstract Full Text Show Details

With ammonia; water; oxygen

T=400°C; Hide Experimental Procedure

Anhui Guangxin Agrochemical Co., Ltd.; Huang, Jinxiang; Guo, Xuejun; Wu, Jianping; Hu, Minghong; Yang, Yaming; Cheng, Weijia; Li, Hongwei; Xu, Xiaobing; Gao, Yanbing; Dai, Yuting

Patent: CN106083651 A, 2016 ; Location in patent: Paragraph 0014; 0015 ; Title/Abstract Full Text Show Details

1; 2:

Salicylonitrile synthesis of new technology, the process includes the following steps: (1) 1 part by weight of o-chlorotoluene, 1.5 parts by weight of ammonia gas, 1.5 parts by weight of oxygen and 2 parts by weight of water vapor were added to the free turbulent fluidized bed reactor,Was added 1 part by weight and the V-Cr-O 1 part by weight of V-P-O-based fine particles of the mixture as a catalyst, the reaction system raised the temperature to 400 deg.] C; (2) after the end of the reaction, the product within the reactor after cooling the condenser cooling crystallization obtained o-chlorobenzonitrile crude products, and then washed, after distillation to get pure o-chlorobenzonitrile,The remaining ammonia in the reactor is transferred to the neutralization tower containing dilute sulfuric acid for absorption; (3) 1.5 parts by weight was added to o-chlorobenzonitrile pure product obtained in step 2 in a concentration of 15percent of an alkali metal alkoxide solution, controlling the reaction temperature at 170 ,Under normal pressure conditions, after the reaction, to stop heating,Until the temperature inside the system naturally cooled to room temperature,The solvent was recovered by distillation under reduced pressure,And then hydrochloric acid added to the system for acidification, can be obtained purity 95percent, the yield of 93percent salicylonitrile solid;The alkali metal alkoxide solution is a mixture of a methanolic solution of sodium methoxide and an ethanol solution of sodium ethoxide in a weight ratio of 1: 2.

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Rx-ID: 9131468 Find similar reactions

99%

Stage #1: With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; tert-butylhypochlorite in dichloromethane

T=20°C; 0.5 h; Inert atmosphere; Stage #2: With ammonia; iodine in dichloromethane; water

T=20°C; 2 h; Inert atmosphere;

Shimojo, Hiroyuki; Moriyama, Katsuhiko; Togo, Hideo

Synthesis (Germany), 2013 , vol. 45, # 15 art. no. SS-2013-F0311-OP, p. 2155 - 2164 Title/Abstract Full Text View citing articles Show Details

95%

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; ammonia; oxygen; copper(II) nitrate in water; dimethyl sulfoxide

T=80°C; P=760.051 Torr; 7 h;

Tao, Chuanzhou; Liu, Feng; Zhu, Youmin; Liu, Weiwei; Cao, Zhiling

Organic and Biomolecular Chemistry, 2013 , vol. 11, # 20 p. 3349 - 3354 Title/Abstract Full Text View citing articles Show Details

91%

With Iron(III) nitrate nonahydrate; ammonium hydroxide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical in acetonitrile

T=20°C; 12 h;

Dighe, Shashikant U.; Chowdhury, Deepan; Batra, Sanjay

Advanced Synthesis and Catalysis, 2014 , vol. 356, # 18 p. 3892 - 3896 Title/Abstract Full Text View citing articles Show Details

90%

With potassium hydroxide; ammonium bicarbonate; tetrabutylammonium peroxydisulfate; copper(II) formate; nikel(II) formate in isopropyl alcohol

T=25°C; 1.5 h;

Chen, Fen-Er; Li, Yong-Ye; Xu, Mei; Jia, Hui-Qing

Synthesis, 2002 , # 13 p. 1804 - 1806 Title/Abstract Full Text View citing articles Show Details

90%

With ammonia; oxygen in tert-Amyl alcohol; water

T=130°C; P=3750.38 Torr; 24 h;

Mao, Fei; Qi, Zhengliang; Fan, Haipeng; Sui, Dejun; Chen, Rizhi; Huang, Jun

RSC Advances, 2017 , vol. 7, # 3 p. 1498 - 1503 Title/Abstract Full Text View citing articles Show Details

82%

With aniline; copper(l) chloride in nitromethane

T=115 - 195°C; 10 h; TemperatureConcentration; Hide Experimental Procedure

Chengdu Chiba Longhua Petroleum Engineering Consulting Co., Ltd; Guan, Genan

Patent: CN105566156 A, 2016 ; Location in patent: Paragraph 0014; 0015 ; Title/Abstract Full Text Show Details

3:Example 3:

In the installation of a stirrer, thermometer,In the reaction vessel of the distillation apparatus,3.1 mol of o-chlorobenzyl alcohol (2), 3.9 mol of aniline (3)Mass fraction 65percent nitromethane 310ml, cuprous chloride 1.56mol, mixing evenly,The stirring speed was controlled at 160 rpm, the solution temperature was raised to 115 & lt; 0 & gt;Reaction 5h, Raising the solution temperature to 135 & lt; 0 & gt; C,Reaction 3h,The temperature of the solution was raised to 195 ° C,Reaction 120min,The solution temperature was lowered to 20 & lt; 0 &Adding ammonium nitrate solution 700ml,Mass fraction of 45percent sodium bisulfite solution 130ml, 1.7kPa vacuum distillation,Fractions of 130-135 ° C were collected,Mass fraction of 75percent triethylamine washing,In the mass fraction of 95percent toluene recrystallization,To obtain the crystal o-chlorobenzonitrile 350.80g, yield 82percent.

80%

With potassium phosphate; ammonium formate in acetonitrile

T=115°C; 16 h; Sealed tubeGreen chemistry;

Molla, Rostam Ali; Ghosh, Kajari; Tuhina; Manirul Islam

New Journal of Chemistry, 2015 , vol. 39, # 2 p. 921 - 930 Title/Abstract Full Text View citing articles Show Details

79%

With tert.-butylhydroperoxide; ammonia; potassium iodide in water

T=60°C; 15 h;

Rajender Reddy; Uma Maheswari; Venkateshwar; Prashanthi; Lakshmi Kantam

Tetrahedron Letters, 2009 , vol. 50, # 18 p. 2050 - 2053 Title/Abstract Full Text View citing articles Show Details

66%

With ammonium hydroxide; sodium periodate; potassium iodide

T=60°C; 3 h;

Zolfigol, Mohammad Ali; Hajjami, Maryam; Ghorbani-Choghamarani, Arash

Bulletin of the Korean Chemical Society, 2011 , vol. 32, # 12 p. 4191 - 4194 Title/Abstract Full Text View citing articles Show Details

35%

With copper(II) choride dihydrate; ammonium formate; potassium carbonate in neat (no solvent) T=135°C; P=760.051 Torr; 24 h; Sealed tubeSchlenk techniqueGreen chemistry;

Yadav, Dilip Kumar T.; Bhanage, Bhalchandra M.

European Journal of Organic Chemistry, 2013 , # 23 p. 5106 - 5110 Title/Abstract Full Text View citing articles Show Details

50 %Chromat.

With ammonium hydroxide; periodic acid; potassium iodide

T=60°C; 131490 h; Sealed tubeGreen chemistry;

Ghorbani-Choghamarani, Arash; Sardari, Sara; Zolfigol, Mohammad Ali; Hajjami, Maryam

Synthetic Communications, 2013 , vol. 43, # 1 p. 52 - 58,7 Title/Abstract Full Text Show Details

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; copper(II) nitrate trihydrate; ammonia; oxygen in water; dimethyl sulfoxide

T=80°C; P=760.051 Torr; 24 h; Sealed tube; Hide Experimental Procedure

Tao, Chuanzhou; Wang, Bin; Sun, Lei; Yi, Jiuyin; Shi, Dahua; Wang, Jian; Liu, Weiwei

Journal of Chemical Research, 2017 , vol. 41, # 1 p. 25 - 29 Title/Abstract Full Text View citing articles Show Details

Cu(NO3)2-catalysed one-pot synthesis of 5-phenyl-1H-tetrazole directly from benzylic alcohols; general procedure

General procedure: Cu(NO3)2·3H2O (0.10 mmol), TEMPO (0.10 mmol), the benzylicalcohol 3 (1.0 mmol) and DMSO (1 mL) were added to a 100 mLround-bottomed flask equipped with a magnetic stirrer. The vesselwas flushed with O2 and aqueous NH3 (25-28percent, 3.0 mmol) was added.The vessel was sealed and the reaction mixture was stirred in an oil bath at 80 °C for 8 h. After cooling to room temperature, the stopper wasremoved and NaN3 (2.0 mmol) was added. Stirring was continued in anoil bath at 120 °C for 16 h. After completion of the reaction, the reactionwas acidified HCl (3 M, pH 1.0). Ethyl acetate (~30 mL) was added,and the mixture was stirred until no solid was present. The organiclayer was separated, and the aqueous layer was extracted with ethylacetate twice. The combined organic layers were washed with saturatedbrine, and concentrated in vacuo. The residue was purified by columnchromatography (silica gel, EtOAc-PE) to afford the product 2. A

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A: 72%

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; N,N-dimethylethylenediamine; copper(l) chloride in toluene

T=80°C; 24 h; Sealed tubeSchlenk technique; chemoselective reaction; Hide Experimental Procedure

Ma, Xian-Tao; Xu, Hao; Xiao, Ying-Lin; Su, Chen-Liang; Liu, Jian-Ping; Xu, Qing

Chinese Chemical Letters, 2017 , vol. 28, # 6 p. 1336 - 1339 Title/Abstract Full Text View citing articles Show Details

Typical procedures for Cu-catalyzed aerobic oxidation of primary amines with air for nitrile synthesis:

General procedure: A mixture of benzylamine 1a (107.0 mg, 1.0 mmol), CuCl (5.0 mg, 0.05 mmol, 5 molpercent), 2,2,6,6-tetramethyl-1-piperidyloxy (TEMPO, 7.8 mg, 0.05 mmol, 5 molpercent), and N,N-dimethylethane-1,2-diamine (DMEDA, 4.4 mg, 0.05 mmol, 5 molpercent) in toluene (0.5 mL) sealed in a Schlenk tube (100 mL) with an air balloon was stirred at 80 °C for 24 h. The reaction was then monitored by TLC and/or GC-MS. After completion of the reaction, solvent was evaporated under vacuum. The residue was purified by scosh column chromatography on silica gel using petroleum ether and ethyl acetate (0–100/1) as the eluent, giving product 2a in 80percent isolated yield

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With P,P-dichlorophenylphosphine oxide; phosphorus pentachloride

T=160°C; 5 h; Hide Experimental Procedure

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Rx-ID: 103124 Find similar reactions

Wu, Jiang; Zhou, Junpeng; Shi, Yalei; Zhu, Jintao

Synthetic Communications, 2016 , vol. 46, # 19 p. 1619 - 1624 Title/Abstract Full Text View citing articles Show Details

Syntheses of Compounds (a-g)

General procedure: A mixture of phenols (100.0 mmol) phenylphosphonic dichloride (11.0 mmol) and phosphorus pentachloride (110.0 mmol) was slowly heated to 160 °C while distilled the byproduct POCl3. And the mixture was stirred at the same temperature for 5 hours. TLC analysis showed the reaction had been finished. The POCl3 was evaporated in vacuum and the residue was poured into ice water, and it was neutralized with saturated aqueous sodium carbonate solution, and extracted with acetic ether. The organic layer was washed with water, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure, the obtained crude product was distilled or purified with silica gel chromatography, the target compound was obtained. The structures of compounds were confirmed by MS and 1H NMR data which were listed as follows. With phosphorus pentachloride

Pfeiffer; Engelhardt; Alfuss

Justus Liebigs Annalen der Chemie, 1928 , vol. 467, p. 171 Full Text Show Details

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Rx-ID: 667296 Find similar reactions

95%

With trimethylsilyl methanesulfonate; phosphorus pentoxide

T=70 - 75°C; 3 h; further reagents;

Rao, C. Someswara; Rambabu, M.; Srinivasan, P. S.

Synthetic Communications, 1989 , vol. 19, # 7,8 p. 1431 - 1436 Title/Abstract Full Text Show Details

93%

With triethylamine; trifluoroacetyl chloride in dichloromethane

Saednya, Akbar

Synthesis, 1985 , # 2 p. 184 - 185 Title/Abstract Full Text Show Details

93%

With C8H14N2O4S in dichloromethane

1 h; Reflux;

Rappai, John P.; Karthikeyan, Jayakumar; Prathapan, Sreedharan; Unnikrishnan, Perupparampil A.

Synthetic Communications, 2011 , vol. 41, # 17 p. 2601 - 2606 Title/Abstract Full Text View citing articles Show Details

91%

With trichloromethyl chloroformate in various solvent(s) 0-5 deg C then heated to 60 deg C, 5 min;

Mai, Khuong; Patil, Ghanshyam

Tetrahedron Letters, 1986 , vol. 27, # 20 p. 2203 - 2206 Title/Abstract Full Text View citing articles Show Details

91%

With trimethylsilylphosphate

0.5 h; Heating;

Yokoyama, Masataka; Yoshida, Sayaka; Imamoto, Tsuneo

Synthesis, 1982 , # 7 p. 591 - 592

Title/Abstract Full Text Show Details

88%

With vanadium oxide on hydrotalcite (V/HT) in 1,3,5trimethyl-benzene

24 h; Reflux;

Sueoka, Shoichiro; Mitsudome, Takato; Mizugaki, Tomoo; Jitsukawa, Koichiro; Kaneda, Kiyotomi

Chemical Communications, 2010 , vol. 46, # 43 p. 8243 - 8245 Title/Abstract Full Text View citing articles Show Details

88%

With Triethoxysilane; [cis-Fe(H)(SPh)(PMe3)4] in tetrahydrofuran

T=60°C; 24 h; Inert atmosphere; Hide Experimental Procedure

Xue, Benjing; Sun, Hongjian; Wang, Yan; Zheng, Tingting; Li, Xiaoyan; Fuhr, Olaf; Fenske, Dieter

Catalysis Communications, 2016 , vol. 86, p. 148 - 150 Title/Abstract Full Text View citing articles Show Details

2.2. General procedure for the dehydration of amides to nitriles

General procedure: To a 25ml Schlenk tube containing a solution of 1 in 2ml of THF was added amide (1.0 mmol) and (EtO)3SiH (0.50 g, 3.0 mmol). The reaction mixture was stirred at 60 °C until there was no amide left (monitored by TLC and GC-MS). The product was purified according to literature procedures by Beller [27]. 85%

84 % Chromat.

With pyridine; phenyl chloroformate in dichloromethane T=0 - 20°C;

Bose; Varadarajan; Vanajatha

Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2001 , vol. 40, # 8 p. 722 - 723 Title/Abstract Full Text View citing articles Show Details

With trichloromethyl chloroformate in tetrahydrofuran

4 h; Heatinginvestigation of the solvent effect of various solvents for the dehydration;

Mai, Khuong; Patil, Ghanshyam

Tetrahedron Letters, 1986 , vol. 27, # 20 p. 2203 - 2206 Title/Abstract Full Text View citing articles Show Details

With thionyl chloride

Borsche; Scriba

Justus Liebigs Annalen der Chemie, 1939 , vol. 541, p. 283,290 Full Text View citing articles Show Details

With aluminium trichloride; sodium chloride

Norris; Klemka

Journal of the American Chemical Society, 1940 , vol. 62, p. 1432,1434 Full Text View citing articles Show Details

With aminosulfonic acid

T=220°C;

Kirsanow; Solotow

Zhurnal Obshchei Khimii, 1950 , vol. 20, p. 284,287 Chem.Abstr., 1950 , p. 6384 Full Text View citing articles Show Details

With sodium tetrahydroborate in diethylene glycol dimethyl ether

T=162°C; 2 h;

Zhu, Hua-Jie; Lu, Kai-Tao; Sun, Guang-Ri; He, Jin-Bao; Li, Hai-Qing; Pittman Jr., Charles U.

New Journal of Chemistry, 2003 , vol. 27, # 2 p. 409 - 413 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 6520242 Find similar reactions

Stage #1: With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; tert-butylhypochlorite in dichloromethane

T=20°C; 0.5 h; Stage #2: With ammonium hydroxide; iodine in dichloromethane

T=20°C; 2 h; Reagent/catalyst; Hide Experimental Procedure

CHIBA UNIVERSITY; GODO SHIGEN COMPANY LIMITED; TOGO, HIDEO; SHIMOJO, HIROYUKI; MORIYAMA, KATSUHIKO; MIYAMOTO, MICHIHIKO

Patent: JP2015/40203 A, 2015 ; Location in patent: Paragraph 0041-0044 ; Title/Abstract Full Text Show Details

General procedure: With respect to 2 mmol of each alcohol represented by the general formula (1), 4 ml of CH 2 Cl 2 as a solvent, 0.05 equivalent of TEMPO as an N-nitrosyl compound, (A) t-BuOCl, (B) I 2 or (C ) N, N'-diiodo-5,5-dimethylhydantoin (DIH) were mixed in a predetermined amount and stirred for a predetermined time at room temperature.Next, 1.5 equivalents of I 2 and 4 ml of aqueous ammonia were added, and the mixture was stirred at room temperature for 2 hours. 93%

With oxygen; copper(II) trifluoroacetate in dimethyl sulfoxide

T=110°C; 26 h; Sealed tubeGreen chemistry; Hide Experimental Procedure

Huaqiao University; Song, Qiuling; Feng, Qiang

Patent: CN103772236 B, 2016 ; Location in patent: Paragraph 0021; 0022; 0023; 0054; 0055; 0056; 0057 ; Title/Abstract Full Text Show Details

12.1:

General procedure: phenylacetic acid or its derivative (0.5mmol), Cu(TFA)2(20mmolpercent), urea (1.5 mmol) was added to the pressure sealed tube containing (0.75mL) of DMSO, after filling oxygen at 130 stirred for about 20h, the process by TLC and GC tracking (specifically the reaction time is determined by GC and TLC tracking results). After the raw material was observed by the GC and TLC the reaction has been completed the reaction, the reaction was removed, cooled to room temperature.To the reaction was added 20mL of ethyl acetate, washed with NaHCO3(20mL × 2), washed with saturated brine 20mL.The combined aqueous phases with ethyl acetate (20mL × 2) after stripping the combined organic phases with anhydrous sodium sulfate. The organic phase was dried by rotary evaporator spin solvent, product was purified by silica gel column, eluent ratio of ethyl acetate: petroleum ether = 50: 1. Benzonitrile obtained in a yield of 84percent. 75%

Jimenez, Leslie S.; Ramanathan, Ahalya

Patent: US2010/331566 A1, 2010 ; Location in patent: Page/Page column 5; 6 ; Title/Abstract Full Text Show Details

TRABERT

Archiv der Pharmazie, 1961 , vol. 294 /66, p. 246 - 254 Title/Abstract Full Text View citing articles Show Details

Fizet,C.; Streith,J.

Tetrahedron Letters, 1974 , p. 3187 - 3188 Full Text View citing articles Show Details

Kanaoka et al.

Chemical and Pharmaceutical Bulletin, 1970 , vol. 18, p. 397,398 Full Text View citing articles Show Details

Luecke; Winter

Chimia, 1971 , vol. 25, p. 94 Full Text View citing articles Show Details

Ikeda et al.

Synthesis, 1978 , p. 301 Full Text View citing articles Show Details

Streith et al.

Helvetica Chimica Acta, 1976 , vol. 59, p. 2786,2790 Full Text View citing articles Show Details

Sonobe

Kogyo Kagaku Zasshi, 1967 , vol. 70, p. 2305,2307 Full Text Show Details

Pfizer Inc.

Patent: US3706747 , 1970 ; Chem.Abstr., vol. 78, # 72187 Full Text Show Details

Nakagawa; Tsuji

Chemical and Pharmaceutical Bulletin, 1963 , vol. 11, p. 296,297 Full Text Show Details

Smith; Walker

Journal of Organic Chemistry, 1962 , vol. 27, p. 4372,4373 Full Text Show Details

Glass; Hoy

Tetrahedron Letters, 1976 , p. 1781 Full Text View citing articles Show Details

Suvorov et al.

Zhurnal Organicheskoi Khimii, 1970 , vol. 6, p. 1219,1225 Full Text Show Details

Cassar

Journal of Organometallic Chemistry, 1973 , vol. 54, p. C57 Full Text View citing articles Show Details

BASF A.G.

Patent: FR1525498 , 1966 ; Chem.Abstr., 1969 , vol. 71, # 80992d Full Text Show Details

Hoechst

Patent: DE2239799 , 1974 ; Chem.Abstr., vol. 80, # 133086 Full Text Show Details

BASF

Patent: DE2310184 , 1974 ; Chem.Abstr., vol. 82, # 4041 Full Text Show Details

Jpn. Chem. Ind.

Patent: DE1230026 , 1966 ; Chem.Abstr., vol. 66, # 55255 Full Text Show Details

Suleimanow et al.

Azerbaidzhanskii Khimicheskii Zhurnal, 1976 , vol. 1, p. 36 Chem.Abstr., 1976 , vol. 85, # 159604 Full Text Show Details

Olah; Keumi

Synthesis, 1979 , p. 112 Full Text Show Details

Norman; Radda

Journal of the Chemical Society, 1961 , p. 3610 Full Text Show Details

Sakanishi; Ogata

Bulletin of the Chemical Society of Japan, 1969 , vol. 42, p. 2502,2503 Full Text Show Details

Urano et al.

Yuki Gosei Kagaku Kyokaishi, 1972 , vol. 30, p. 154,158,159 Full Text Show Details

Hodgkins; King

Journal of the American Chemical Society, 1963 , vol. 85, p. 2679,2680 Full Text Show Details

Crawford; Woo

Canadian Journal of Chemistry, 1965 , vol. 43, p. 3178,3187 Full Text Show Details

Gruenanger; Langella

Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti, 1964 , vol. 36, # 3 p. 387,388-390 Chem.Abstr., 1965 , vol. 62, # 3973g Full Text Show Details

Becke; Burger

Justus Liebigs Annalen der Chemie, 1968 , vol. 716, p. 78 Full Text Show Details

Hide Experimental Procedure

ENICHEM SYNTHESIS S.p.A.

Patent: EP441004 A1, 1991 ; Title/Abstract Full Text Show Details

Examples of aromatic nitriles (I) which can be prepared by the process according to the present invention are: para-chloro-benzonitrile; meta-chloro-benzonitrile; ortho-chloro-benzonitrile; 2-fluoro-benzonitrile; 2,3-di-chloro-benzonitrile; 3,4-di-chloro-benzonitrile; 2,3,4-tri-chloro-benzonitrile; 2,4,5-tri-chloro-benzonitrile; 3,4,5-tri-chloro-benzonitrile; ...

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ENICHEM SYNTHESIS S.p.A.

Patent: EP441004 A1, 1991 ; Title/Abstract Full Text Show Details

Process according to claim 1, characterized in that the following nitriles (I) are prepared: para-chloro-benzonitrile; meta-chloro-benzonitrile; ortho-chloro-benzonitrile; 2-fluoro-benzonitrile; 2,3-di-chloro-benzonitrile; 3,4-di-chloro-benzonitrile; 2,3,4-tri-chloro-benzonitrile; 2,4,5-tri-chloro-benzonitrile; 3,4,5-tri-chloro-benzonitrile; ...

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Rx-ID: 36713507 Find similar reactions

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97%

T=350°C; P=48754.9 Torr; 0.416667 h; Supercritical conditionsFlow reactor;

Cantillo, David; Kappe, C. Oliver

Journal of Organic Chemistry, 2013 , vol. 78, # 20 p. 10567 - 10571 Title/Abstract Full Text View citing articles Show Details

28%

With molybdenum hexacarbonyl in tetrachloromethane

T=150°C; 6 h; Autoclave; Hide Experimental Procedure

Khusnutdinov; Shchadneva; Bayguzina; Mayakova, Yu. Yu.

Russian Journal of Organic Chemistry, 2016 , vol. 52, # 9 p. 1282 - 1286 Zh. Org. Khim., 2016 , vol. 52, # 9 p. 1295 - 1299,5 Title/Abstract Full Text View citing articles Show Details

General procedure: General procedure for the reaction of acetonitrilewith carboxylic acids. A 17-mL stainless-steelhigh-pressure microreactor was charged with 1 mmolof Mo(CO)6 or VO(acac)2, 100 mmol of carboxylicacid, 500 mmol of acetonitrile, and 50 mmol of carbontetrachloride. The reactor was hermetically closed andheated for 6 h at 150°C. When the reaction wascomplete, the reactor was cooled to room temperatureand opened, the mixture was filtered through a layer ofAl2O3, unreacted acetonitrile and carbon tetrachloridewere distilled off, and the residue was distilled underatmospheric or reduced pressure or recrystallized fromethanol.

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Rx-ID: 38673590 Find similar reactions

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93%

With mesoporous silica SBA-15 supported Cu2O nanoparticles in N,N-dimethyl-formamide

T=120°C; 8 h; Green chemistry;

Yin, Wenzhu; Liu, Rui; He, Guangke; Lv, Wangjie; Zhu, Hongjun

RSC Advances, 2014 , vol. 4, # 71 p. 37773 - 37778 Title/Abstract Full Text View citing articles Show Details

26%

With 3 Pd/CeO2; sodium acetate in N,N-dimethylformamide; isopropyl alcohol

T=55°C; 12 h; Irradiation; Hide Experimental Procedure

Nanjing University of Technology; Guo, Cheng; Gong, Xubin; Wu, Lou; Li, Qing; Wang, Jianjiang

Patent: CN105777579 A, 2016 ; Location in patent: Paragraph 0050; 0051 ; Title/Abstract Full Text Show Details

17:Example 17: Photocatalytic synthesis of compound 2-chlorobenzonitrile

In a 25 mL screw test tube, 0.25 mmol of 2-chloroiodobenzene, 0 l mmol of cyanoating agent K4 [Fe (CN) 6], sodium acetate 0 · 25 mmol, 100 mg 3 wtpercent Pd / CeO2, and then 7 mL of N, N-dimethylformamide and lmL isopropanol were mixed with Machine solvent to test tube, 500W visible light irradiation under the magnetic stirring reaction, control visible light intensity of 0.74W / cm2, the reaction Temperature of 55 ° C, 12 hours after the reaction to stop the reaction, take a small amount of reaction solution by microporous membrane filtration, methanol solvent dilution The samples were tested in liquid phase. The samples to be tested were compared with the 2-chloroiodobenzene standard and the 2-chlorobenzonitrile standard. The conversion of the reaction substrate was 41.2percent, the selectivity of the target product was 72.1percent, and the liquid product yield was 29.7percent. Post-processing Method for washing with a cloth funnel filter catalyst, drying for recycling use; reaction solution by dichloromethane and water mixture After the solution was extracted, the organic layer was concentrated and the final product 2-chlorobenzonitrile was obtained by column chromatography. The isolated yield was 26percent

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Rx-ID: 41758405 Find similar reactions

72%

With aluminum (III) chloride; sodium nitrite in N,Ndimethyl-formamide

T=90°C; 8 h; Schlenk technique;

Ge, Jing-Jie; Yao, Chuan-Zhi; Wang, Mei-Mei; Zheng, Hong-Xing; Kang, Yan-Biao; Li, Yadong

Organic Letters, 2016 , vol. 18, # 2 p. 228 - 231 Title/Abstract Full Text View citing articles Show Details

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Synthesize Find similar Rx-ID: 42199580 Find similar reactions

With [2,2]bipyridinyl; ammonium hydroxide; copper(l) iodide; N,N-dimethyl-(4-(2,2,6,6-tetramethyl-1-oxyl-4piperidoxyl)butyl)dodecylammonium bromide; oxygen in neat (no solvent) T=55°C; P=750.075 Torr; 9 h; Green chemistry; Overall yield = 61.6 percent;

Zhang, Yuecheng; Huang, Rong; Gao, Baosheng; Zhao, Jiquan

Catalysis Letters, 2016 , vol. 146, # 1 p. 220 - 228 Title/Abstract Full Text View citing articles Show Details

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With formic acid; sodium nitrite in acetonitrile

T=70°C; 4 h; Schlenk technique; Hide Experimental Procedure

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Rx-ID: 42735682 Find similar reactions

Liu, Qiang; Fang, Bao; Bai, Xiaohui; Liu, Yuan; Wu, Yao; Xu, Guiming; Guo, Cancheng

Tetrahedron Letters, 2016 , vol. 57, # 24 p. 2620 - 2623 Title/Abstract Full Text View citing articles Show Details

2. Typical procedure for the synthesis of nitriles from olefins General procedure: A Schlenk tube was charged with olefins 1 (0.4 mmol), NaNO2 (138 mg, 2 mmol), HCOOH (0.5 mL, 10 mmol), and CH3CN(4.5mL). The reaction mixture was stirred at 70 °C under air atmosphere for 4 h. After cooling to room temperature, the solution was filtered to remove the solid by-product then was washed with ethyl acetate (3×10 mL). The solution was concentrated under vacuum and purified by column chromatography on silica gel (eluent: petroleum ether/ethyl acetate) to obtain the desired product 2.

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With oxygen; copper(l) cyanide in dimethyl sulfoxide

T=150°C;

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Rx-ID: 43205215 Find similar reactions

Gu, Lijun; Jin, Cheng; Zhang, Hongtao; Liu, Jiyan; Li, Ganpeng; Yang, Zhi

Organic and Biomolecular Chemistry, 2016 , vol. 14, # 28 p. 6687 - 6690 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 43737377 Find similar reactions

75%

With tetrachloromethane; bis(acetylacetonate)oxovanadium

T=150°C; 6 h; Autoclave; Hide Experimental Procedure

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Khusnutdinov; Shchadneva; Bayguzina; Mayakova, Yu. Yu.

Russian Journal of Organic Chemistry, 2016 , vol. 52, # 9 p. 1282 - 1286 Zh. Org. Khim., 2016 , vol. 52, # 9 p. 1295 - 1299,5 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 44061850 Find similar reactions

94%

With potassium phenolate; palladium diacetate; potassium carbonate; dimethyl cis-but-2-ene1,4-dioate; triphenylphosphine in N,N-dimethylformamide

T=120°C; 24 h; Schlenk techniqueInert atmosphere;

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Maestri, Giovanni; Cañeque, Tatiana; Della Ca, Nicola; Derat, Etienne; Catellani, Marta; Chiusoli, Gian Paolo; Malacria, Max

Organic Letters, 2016 , vol. 18, # 23 p. 6108 - 6111 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 44061858 Find similar reactions

78%

With potassium phenolate; palladium diacetate; potassium carbonate; dimethyl cis-but-2-ene1,4-dioate; triphenylphosphine in N,N-dimethylformamide

T=120°C; 24 h; Schlenk techniqueInert atmosphere;

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Maestri, Giovanni; Cañeque, Tatiana; Della Ca, Nicola; Derat, Etienne; Catellani, Marta; Chiusoli, Gian Paolo; Malacria, Max

Organic Letters, 2016 , vol. 18, # 23 p. 6108 - 6111 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 39376037 Find similar reactions

58%

With tert.-butylhydroperoxide; copper(II) nitrate trihydrate; water; acetic acid

T=140°C; 40 h; chemoselective reaction;

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Zhang, Lianpeng; Lu, Ping; Wang, Yanguang

Chemical Communications, 2015 , vol. 51, # 14 p. 2840 - 2843 Title/Abstract Full Text View citing articles Show Details

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Synthesize Find similar Rx-ID: 39755364 Find similar reactions

A: 60% B: 52%

With sodium azide; CuCl2·2H2O; oxygen in DMFA

T=100°C; 10 h; Schlenk techniqueSealed tube;

Gu, Lijun; Jin, Cheng

Chemical Communications, 2015 , vol. 51, # 30 p. 6572 - 6575 Title/Abstract Full Text View citing articles Show Details

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Synthesize Find similar Rx-ID: 41313856 Find similar reactions

With methyltriethylammonium methylsulfate in acetonitrile

T=20°C; Electrolysis;

Hartmer, Marius F.; Waldvogel, Siegfried R.

Chemical Communications, 2015 , vol. 51, # 91 p. 16346 - 16348 Title/Abstract Full Text View citing articles Show Details

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Synthesize Find similar Rx-ID: 41483102 Find similar reactions

A: 102 g B: 93.5% C: 210 g

Stage #1: With water; chlorine in chlorobenzene

T=20 - 65°C; 3 h; Stage #2: With sodium hydroxide in water

T=60 - 65°C; pH=9 - 10; Stage #3: With hydrochlorid acid in water

T=20 - 30°C; pH=3 - 4; Hide Experimental Procedure

Shouguang Syntech Fine Chemical Co., Ltd.; DAI, Mingben

Patent: US2015/336910 A1, 2015 ; Location in patent: Paragraph 0262; 0263 ; Title/Abstract Full Text Show Details

1.b; 1.c; 1.d:Example 1 According to step b) 381 g of the organic layer, comprising 2-(octadecylthio)benzonitrile (IV) obtained in step a), 100 g of chlorobenzene and 32 g of water are added into a 1000 ml four-necked flask with a stirrer, a thermometer and a condenser. At a temperature in the range of from 20 to 30° C., 53 g chlorine are blown into the mixture over a period of 2 hours. The mixture is further heated to a temperature in the range of from 60 to 65° C. and then allowed to further react for 1 h. During the reaction the reaction mixture (RM) is formed. After completion of the reaction the reaction mixture (RM) is cooled to a temperature in the range of from 20 to 30° C. and according to step c) 200g of water are added to the reaction mixture (RM). A 32percent by weight sodium hydroxide solution is added dropwise to the reaction mixture (RM) to give a pH-value in the range of from 9 to 10. The mixture is heated to a temperature in the range of from 60 to 65° C. and according to step d) separated into a first phase and a second phase. The first phase is cooled to a temperature in the range of from 20 to 30° C. A 31percent by weight hydrochloric acid solution is added dropwise to the first phase to give a pH-value in the range of from 3 to 4. Crystals of 1,2-benzisothiazolin-3-one precipitate. The precipitated crystals are collected by filtration, washed with water, and dried to obtain 1,2-benzisothiazolin-3-one (I) (102 g, HPLC>99percent), the yield to 2-chlorobenzonitrile (II) is 93.5percent.The second phase (420 g) is distilled to obtain 1-chlorooctadecane (V) (210 g). 210 g of the 1-chlorooctadecane (V), 200 g of chlorobenzene, 180 g of a 32percent by weight sodium bisulfide solution in water and 6 g of tetra-butylammonium bromide are added into a 1000 ml four-necked flask with a stirrer, a thermometer and a condenser. At a temperature in the range of from 65 to 70° C., the mixture is reacted for 16 h. The mixture is separated into an aqueous layer and an organic layer. The organic layer is n-octadecanethiol (III) (405 g). A

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A: 106 g B: 97.2% C: 143 g

Stage #1: With sulfuryl chloride; water in chlorobenzene

T=20 - 65°C; 3 h; Stage #2: With sodium hydroxide in water

T=60 - 65°C; pH=9 - 10; Stage #3: With hydrochlorid acid in water

T=20 - 30°C; pH=3 - 4; Reagent/catalyst; Hide Experimental Procedure

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Shouguang Syntech Fine Chemical Co., Ltd.; DAI, Mingben

Patent: US2015/336910 A1, 2015 ; Location in patent: Paragraph 0276; 0277 ; Title/Abstract Full Text Show Details

5.b; 5.c; 5.d:Example 5 According to step b) 320g of the organic layer, comprising the 2-(dodecylthio)benzonitrile (IV) obtained in step a), 200 g of chlorobenzene and 30 g of water are added into a 1000 ml four-necked flask with a stirrer, a thermometer and a condenser. At a temperature in the range of from 20 to 30° C., 100 g sulfuryl chloride are added dropwise to the mixture over a period of 2 hours. The mixture is further heated to a temperature in the range of from 60 to 65° C. and then allowed to further react for 1 h. During the reaction the reaction mixture (RM) is formed. After completion of the reaction the reaction mixture (RM) is cooled to a temperature in the range of from 20 to 30° C. and according to step c) 200 g of water are added to the reaction mixture (RM). A 32percent by weight sodium hydroxide solution is added dropwise to the reaction mixture (RM) to give a pHvalue in the range of from 9 to 10. The mixture is heated to a temperature in the range of from 60 to 65° C. and according to step d) separated into a first phase and a second phase. The first phase is cooled to a temperature in the range of from 20 to 30° C. A 31percent by weight hydrochloric acid solution is added dropwise to the first phase to give a pH-value in the range of from 3 to 4. Crystals of 1,2-benzisothiazolin-3-one (I) precipitate. The precipitated crystals are collected by filtration, washed with water, and dried to obtain 1,2-benzisothiazolin-3-one (I) (106 g, HPLC>99percent), the yield to 2-chlorobenzonitrile (II) is 97.2percent. (0277) The second phase (445 g) is distilled to obtain n-chlorododecane (V) (143 g). 143 g of the n-chlorododecane (V), 100 g of chlorobenzene, 180 g of a 32percent by weight sodium bisulfide solution in water and 4 g of tetra-butylammonium bromide are added into a 1000 ml four-necked flask with a stirrer, a thermometer and a condenser. At a temperature in the range of from 65 to 70° C., the mixture is reacted for 12 h. The mixture is separated into an aqueous layer and an organic layer. The organic layer is n-dodecanethiol (III) (244 g). A

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A: 103 g B: 94.5% C: 100 g

Stage #1: With water; chlorine in chlorobenzene

T=20 - 65°C; 3 h; Stage #2: With sodium hydroxide in water

T=60 - 65°C; pH=9 - 10; Stage #3: With hydrochlorid acid in water

T=20 - 30°C; pH=3 - 4; Hide Experimental Procedure

Shouguang Syntech Fine Chemical Co., Ltd.; DAI, Mingben

Patent: US2015/336910 A1, 2015 ; Location in patent: Paragraph 0266; 0267 ; Title/Abstract Full Text Show Details

2.b; 2.c; 2.d:Example 2 According to step b) 279 g of the organic layer, comprising the 2-(octylthio)benzonitrile (IV) obtained in step a), 200 g of chlorobenzene and 32 g of water are added into a 1000 ml four-necked flask with a stirrer, a thermometer and a condenser. At a temperature in the range of from 20 to 30° C., 54 g chlorine are blown into the mixture over a period of 2 hours. The mixture is further heated to a temperature in the range of from 60 to 65° C. and then allowed to further react for 1 h. During the reaction the reaction mixture (RM) is formed. After completion of the reaction the reaction mixture (RM) is cooled to a temperature in the range of from 20 to 30° C. and according to step c) 200 g of water are added to the reaction mixture (RM). A 32percent by weight sodium hydroxide solution is added dropwise to the reaction mixture (RM) to give a pH-value in the range of from 9 to 10. The mixture is heated to a temperature in the range of from 60 to 65° C. and according to step d) separated into a first phase and a second phase. The first phase is cooled to a temperature in the range of from 20 to 30° C. A 31percent by weight hydrochloric acid solution is added dropwise to the first phase to give a pH-value in the range of from 3 to 4. Crystals of 1,2-benzisothiazolin-3-one (I) precipitate. The precipitated crystals are collected by filtration, washed with water, and dried to obtain 1,2-benzisothiazolin-3-one (I) (103 g, HPLC>99percent), the yield to 2-chlorobenzonitrile (II) is 94.5percent. (0267) The second phase (310 g) is distilled to obtain 1-chlorooctane (V) (100 g). 100 g of the 1-chlorooctadecane (V), 200 g of chlorobenzene, 167 g of a 32percent by weight sodium bisulfide solution in water and 4 g of tetra-butylammonium bromide are added into a 1000 ml four-necked flask with a stirrer, a thermometer and a condenser. At a temperature in the range of from 65 to 70° C., the mixture is reacted for 12 h. The mixture is separated into an aqueous layer and an organic layer. The organic layer is n-octanethiol (Ill) (196 g). A

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A: 10% B: 43%

With tert.-butylhydroperoxide; tetraethylammonium iodide; ammonium hydrogen carbonate in 1,2-dichloroethane

T=70°C; 22 h;

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Wang, Gao; Yu, Qing-Ying; Chen, Shan-Yong; Yu, Xiao-Qi

Organic and Biomolecular Chemistry, 2014 , vol. 12, # 3 p. 414 - 417 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar Multi-step reaction with 2 steps 1: iodine / water / 20 °C / |Green chemistry 2: ammonia / water / 20 °C / |Green chemistry View Scheme

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Rx-ID: 37685363 Find similar reactions

Yadav, Arvind K.; Srivastava, Vishnu P.; Yadav, Lal Dhar S.

Synthetic Communications, 2014 , vol. 44, # 3 p. 408 - 416 Title/Abstract Full Text View citing articles Show Details

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T=20°C; Green chemistry; Hide Experimental Procedure

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Rx-ID: 37685441 Find similar reactions

Yadav, Arvind K.; Srivastava, Vishnu P.; Yadav, Lal Dhar S.

Synthetic Communications, 2014 , vol. 44, # 3 p. 408 - 416 Title/Abstract Full Text View citing articles Show Details

General Procedure for the One-Pot Synthesis of Primary Thioamides 3

General procedure: A mixture of aldehyde 1 (1.5 mmol) and iodine (1.6 mmol) in ammonia water (10 mL of 28percent solution) was stirred at room temperature for 30 min. The dark reaction mixture fainted in colour at the end of reaction. The excess of ammonia was removed by stirring at 90 °C. Then, O,O-diethyl dithiophosphoric acid (2) (1.5 mmol) was added and the reaction mixture was stirred at 90 °C for 2-4 h (Table 2). After completion of the reaction (monitored by TLC), the mixture was cooled to r.t. The product thus precipitated was filtered, washed with aqueous sodium thiosulfate solution followed by water and dried under reduced pressure to give pure primary thioamides 3 (Table 2).

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With oxygen; cupric trifluoroacetate; urea in dimethyl sulfoxide

T=110°C; 26 h; Green chemistry;

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Rx-ID: 37873191 Find similar reactions

Feng, Qiang; Song, Qiuling

Advanced Synthesis and Catalysis, 2014 , vol. 356, # 8 p. 1697 - 1702 Title/Abstract Full Text View citing articles Show Details

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With N-benzyl-N,N,N-triethylammonium chloride; copper dichloride; CSA; sodium nitrite in acetic acid

T=20°C; 24 h; TimeSolvent; Hide Experimental Procedure

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Rx-ID: 29687998 Find similar reactions

Vajpayee, Vaishali; Moon, Mi Eun; Lee, Sunmi; Ravikumar, Sambandam; Kim, Hyunuk; Ahn, Byungchan; Choi, Seoyoon; Hong, Soon Ho; Chi, Ki-Whan

Tetrahedron, 2013 , vol. 69, # 16 p. 3511 - 3517 Title/Abstract Full Text View citing articles Show Details

3.4.4 Diazotization–halogenation to aryl chlorides 7 arenediazonium camphorsulfonate

General procedure: Camphorsulfonic acid (3.0 mmol), tert-butyl nitrite (3.0 mmol), benzyltriethylammonium chloride (5.0 mmol), and catalytic amounts of copper chloride (1 mol percent) were added to an acetonitrile solution (30 ml) of aniline (2.5 mmol). The reaction mixture was stirred at 60 °C for 24 h (Tables 1 and 2). The evolution of N2 was immediately observed. The solvent was removed by rotary evaporator after completion of the reaction (confirmed by β-naphthol test and TLC). The crude residue was purified via column chromatography by using hexane/dichloromethane as the eluting solvent. Physical and 1H NMR data were identical to those of a commercially available sample of analytical purity.

61%

With tert.-butylnitrite; N-benzyl-N,N,N-triethylammonium chloride; toluene-4-sulfonic acid; copper dichloride in acetonitrile

T=20°C; 24 h;

Lee, Young Min; Moon, Mi Eun; Vajpayee, Vaishali; Filimonov, Victor D.; Chi, Ki-Whan

Tetrahedron, 2010 , vol. 66, # 37 p. 7418 - 7422 Title/Abstract Full Text View citing articles Show Details

33%

With tert.-butylnitrite; N-benzyl-N,N,N-triethylammonium chloride; toluene-4-sulfonic acid; copper dichloride

Moon, Mi Eun; Choi, Younghwa; Lee, Young Min; Vajpayee, Vaishali; Trusova, Marina; Filimonov, Victor D.; Chi, Ki-Whan

Tetrahedron Letters, 2010 , vol. 51, # 51 p. 6769 - 6771 Title/Abstract Full Text View citing articles Show Details

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With ammonia; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3dione in water; acetonitrile

T=70°C; Hide Experimental Procedure

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Rx-ID: 31423989 Find similar reactions

Deshmukh, Swapnil S.; Huddar, Sameerana N.; Jadhav, Ravindra R.; Akamanchi, Krishnacharya G.

Tetrahedron Letters, 2011 , vol. 52, # 35 p. 4533 - 4536 Title/Abstract Full Text View citing articles Show Details

General procedure for oxidative fragmentation of oxiranes.

General procedure: To a stirred solution of IBX (10.0 mmol) in aqueous ammonia (25 mL of a 28-30percent solution) was added oxirane (5.0 mmol) in 5 mL of acetonitrile in one portion. The reaction mixture was stirred at 70 °C until complete consumption of starting material as observed on TLC (up to 4 h). After completion of reaction, the reaction mixture was extracted with chloroform (2 .x. 15 mL). The organic layer was washed with water (2 .x. 10 mL); bisulfate solution (15 mL) followed by water (10 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to give crude product. Pure product was obtained after column chromatography (silica gel, mesh size 60-120, eluent ethyl acetate/hexane 05:95). 83%

With ammonia; iodine in water; acetonitrile

T=70°C;

Jadhav, Ravindra R.; Akamanchi, Krishnacharya G.

Chemistry Letters, 2013 , vol. 42, # 2 p. 162 - 164 Title/Abstract Full Text View citing articles Show Details

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With N-chloro-succinimide; palladium diacetate; toluene4-sulfonic acid in 1,2-dichloro-ethane T=70°C; 12 h; Sealed tube;

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Rx-ID: 35155084 Find similar reactions

Du, Bingnan; Jiang, Xiaoqing; Sun, Peipei

Journal of Organic Chemistry, 2013 , vol. 78, # 6 p. 2786 - 2791 Title/Abstract Full Text View citing articles Show Details

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Synthesize Find similar Rx-ID: 35229051 Find similar reactions

B: 87%

With [Ru(η6C6Me6)Cl2(tris(dimethylamino)phosphine)]; hydroxylamine hydrochloride; sodium hydrogencarbonate in water

T=100°C; 7 h; Inert atmosphereSealed tubeGreen chemistry;

Garcia-Alvarez, Rocio; Diaz-Alvarez, Alba E.; Crochet, Pascale; Cadierno, Victorio

RSC Advances, 2013 , vol. 3, # 17 p. 5889 - 5894 Title/Abstract Full Text View citing articles Show Details

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Synthesize Find similar Rx-ID: 35258461 Find similar reactions

With 4H2O*6K(1+)*PW9V3O40(6); ammonia; water; dihydrogen peroxide in isopropyl alcohol

T=25°C; 10 h;

Xue, Xiaoling; Song, Fangyuan; Ma, Baochun; Yu, Yongze; Li, Cheng; Ding, Yong

Catalysis Communications, 2013 , vol. 33, p. 61 - 65 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 32300638 Find similar reactions

82%

With [Pd{C6H4(CH2N(CH2Ph)2)}(μBr)]2; tetrabutylammomium bromide; potassium carbonate in N,N-dimethyl-formamide

T=130°C; 0.166667 h; Microwave irradiation; chemoselective reaction; Hide Experimental Procedure

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Hajipour, Abdol Reza; Rafiee, Fatemeh; Ruoho, Arnold E.

Tetrahedron Letters, 2012 , vol. 53, # 5 p. 526 - 529 Title/Abstract Full Text View citing articles Show Details

General procedure for cyanation reaction of aryl halides with K4[Fe(CN)6] under microwave irradiation

General procedure: A mixture of the aryl halide (1 mmol), K4[Fe(CN)6]*3 H2O (0.22 mmol, 92.9 mg), TBAB (1 mmol, 322.4 mg), palladacycle catalyst (0.5 mmol percent, 4.7 mg), and K2CO3 (1 mmol, 138.2 mg) was added to DMF (3 mL) in a round-bottomed flask equipped with a condenser and placed into the Milestone microwave. Initially using a microwave power of 600 W the temperature was ramped from room temperature to 130 °C, this taking approximately 1 min, and then held at this temperature until the reaction was completed. During this time, the power was modulated automatically to keep the reaction mixture at 130 °C. The mixture was stirred continuously using an appropriate magnet during the reaction. After the reaction was completed, the mixture was cooled to room temperature and diluted with water (30 ml) and ethyl acetate (30 ml). The organic layer was dried over MgSO4, filtered, and the solvent was evaporated using rotary evaporator. The residue was purified by silica gel column chromatography or by recrystallization using ethanol and water. The products were characterized by comparing their mp, IR, 1H, 13C NMR spectra with those found in the literature. [19] and [20] A

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Rx-ID: 32545805 Find similar reactions

B: 20%

With triethylamine in dichloromethane

T=20°C; 0.333333 h;

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Moussa, Ziad

Synthesis, 2012 , vol. 44, # 3 art. no. T105811SS, p. 460 - 468 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 33236828 Find similar reactions

68%

With [Pd{C6H3(CH2CH2NH2)-4-OMe-5-κ2-C,N}(μBr)]2; potassium carbonate in N,N-dimethyl-formamide

T=130°C; 0.25 h; Microwave irradiation; chemoselective reaction;

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Hajipour, Abdol-Reza; Abrisham, Fatemeh; Tavakoli, Ghazal

Transition Metal Chemistry, 2011 , vol. 36, # 7 p. 725 - 730 Title/Abstract Full Text View citing articles Show Details

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With 0.60mol Pd/C; hydrogen; sodium hydrogencarbonate in methanol

T=20°C; 0.75 h; regioselective reaction;

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Rx-ID: 29174726 Find similar reactions

Ramanathan, Ahalya; Jimenez, Leslie S.

Synthesis, 2010 , # 2 art. no. M04609SS, p. 217 - 220 Title/Abstract Full Text View citing articles Show Details

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Synthesize Find similar Rx-ID: 29622620 Find similar reactions

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A: 84% B: 10%

With tetraethylammonium bromide; 1-hydroxy-3Hbenz[d][1,2]iodoxole-1,3-dione in acetonitrile

T=20°C; 0.75 h;

Deshmukh, Swapnil S.; Huddar, Sameerana N.; Bhalerao, Dinesh S.; Akamanchi, Krishnacharya G.

Arkivoc, 2010 , vol. 2010, # 2 p. 118 - 126 Title/Abstract Full Text View citing articles Show Details

A: 8% B: 81%

With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione in water; acetonitrile

T=20°C; 0.75 h;

Deshmukh, Swapnil S.; Huddar, Sameerana N.; Bhalerao, Dinesh S.; Akamanchi, Krishnacharya G.

Arkivoc, 2010 , vol. 2010, # 2 p. 118 - 126 Title/Abstract Full Text View citing articles Show Details

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Synthesize Find similar Rx-ID: 29760043 Find similar reactions

A: 38 %Spectr. B: 29 %Spectr. C: 6 %Spectr. D: 23 %Spectr.

With lithium diisopropyl amide in tetrahydrofuran; hexane

T=-98°C; Inert atmosphere;

Vitale, Paola; Di Nunno, Leonardo; Scilimati, Antonio

Synthesis, 2010 , # 18 p. 3195 - 3203 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 29893160

Find similar 90%

With hydroxylammonium sulphate; zinc

0.416667 h; Microwave irradiation;

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Find similar reactions

Cao, Yu-Qing; Qu, An-Li; Liu, Rui-Yan; Duan, Chun-Ming

Journal of Chemical Research, 2010 , # 7 p. 414 - 415 Title/Abstract Full Text View citing articles Show Details

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Synthesize Find similar Rx-ID: 28945776 Find similar reactions

A: 50%

With tetrabutylammomium bromide; 1-hydroxy-3Hbenz[d][1,2]iodoxole-1,3-dione in acetonitrile

T=20°C; 0.0833333 h; Inert atmosphereMolecular sieve;

Drouet, Fleur; Fontaine, Patrice; Masson, Geraldine; Zhu, Jieping

Synthesis, 2009 , # 8 art. no. T19708SS, p. 1370 - 1374 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 28167332 Find similar reactions

68 %Chromat.

With 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; sodium carbonate in N,N-dimethyl acetamide

T=140°C; 24 h; Inert atmosphere;

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Zhu, Yi-Zhong; Cai, Chun

Synthetic Communications, 2008 , vol. 38, # 16 p. 2753 - 2760 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 28231824 Find similar reactions

A: 30% B: 21% C: 40%

in tetrahydrofuran; hexanes

T=0°C; 1 h; Inert atmosphere;

Di Nunno, Leonardo; Vitale, Paola; Scilimati, Antonio

Tetrahedron, 2008 , vol. 64, # 49 p. 11198 - 11204 Title/Abstract Full Text View citing articles Show Details

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Synthesize Find similar Rx-ID: 11109773 Find similar reactions

With ammonium hydroxide; 1,3-Diiodo-5,5-dimethyl-2,4imidazolidinedione

T=60°C; 3 h;

Iida, Shinpei; Togo, Hideo

Tetrahedron, 2007 , vol. 63, # 34 p. 8274 - 8281 Title/Abstract Full Text View citing articles Show Details

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Synthesize Find similar Rx-ID: 11109775 Find similar reactions

With ammonium hydroxide; 1,3-Diiodo-5,5-dimethyl-2,4imidazolidinedione

T=60°C; 4 h;

Iida, Shinpei; Togo, Hideo

Tetrahedron, 2007 , vol. 63, # 34 p. 8274 - 8281 Title/Abstract Full Text View citing articles Show Details

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Find similar Rx-ID: 9536149 Find similar reactions

Find similar

A: 32 % Chromat. B: 23 % Chromat.

With sodium tetrahydroborate; lithium chloride in diethylene glycol dimethyl ether

T=162°C; 3 h; Title compound not separated from byproducts.;

Zhu, Hua-Jie; Lu, Kai-Tao; Sun, Guang-Ri; He, Jin-Bao; Li, Hai-Qing; Pittman Jr., Charles U.

New Journal of Chemistry, 2003 , vol. 27, # 2 p. 409 - 413 Title/Abstract Full Text View citing articles Show Details

A: 36 % Chromat. B: 1.5 % Chromat.

With lithium aluminium tetrahydride in tetrahydrofuran

T=20 - 78°C; 1 h; Title compound not separated from byproducts.;

Zhu, Hua-Jie; Lu, Kai-Tao; Sun, Guang-Ri; He, Jin-Bao; Li, Hai-Qing; Pittman Jr., Charles U.

New Journal of Chemistry, 2003 , vol. 27, # 2 p. 409 - 413 Title/Abstract Full Text View citing articles Show Details

A: 2 % Chromat. B: 14 % Chromat.

With lithium aluminium tetrahydride in tetrahydrofuran

T=78°C; 1 h; Title compound not separated from byproducts.;

Zhu, Hua-Jie; Lu, Kai-Tao; Sun, Guang-Ri; He, Jin-Bao; Li, Hai-Qing; Pittman Jr., Charles U.

New Journal of Chemistry, 2003 , vol. 27, # 2 p. 409 - 413 Title/Abstract Full Text View citing articles Show Details

A: 16 % Chromat. B: 55 % Chromat.

With sodium tetrahydroborate; lithium chloride in diethylene glycol dimethyl ether

T=162°C; 5.5 h; Title compound not separated from byproducts.;

Zhu, Hua-Jie; Lu, Kai-Tao; Sun, Guang-Ri; He, Jin-Bao; Li, Hai-Qing; Pittman Jr., Charles U.

New Journal of Chemistry, 2003 , vol. 27, # 2 p. 409 - 413 Title/Abstract Full Text View citing articles Show Details

A: 77 % Chromat. B: 4 % Chromat.

With sodium tetrahydroborate in diethylene glycol dimethyl ether

T=162°C; 2.6 h; Title compound not separated from byproducts.;

Zhu, Hua-Jie; Lu, Kai-Tao; Sun, Guang-Ri; He, Jin-Bao; Li, Hai-Qing; Pittman Jr., Charles U.

New Journal of Chemistry, 2003 , vol. 27, # 2 p. 409 - 413 Title/Abstract Full Text View citing articles Show Details

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Synthesize Find similar Rx-ID: 9072577 Find similar reactions

With trichlorophosphate in acetonitrile

3 h; Heating;

Janin, Yves L.; Roulland, Emmanuel; Beurdeley-Thomas, Arnaud; Decaudin, Didier; Monneret, Claude; Poupon, Marie-France

Journal of the Chemical Society. Perkin Transactions 1, 2002 , # 4 p. 529 - 532 Title/Abstract Full Text View citing articles Show Details

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With zirconium tetrachloride in nitromethane

0.0333333 h; Heating;

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Rx-ID: 9275506 Find similar reactions

Tsuji, Chiho; Miyazawa, Etsuko; Sakamoto, Takeshi; Kikugawa, Yasuo

Synthetic Communications, 2002 , vol. 32, # 24 p. 3871 - 3879 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar Multi-step reaction with 2 steps 1: acetonitrile; H2O / 0.17 h 2: 86 percent / ZrCl4 / nitromethane / 0.03 h / Heating View Scheme

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Rx-ID: 14441182 Find similar reactions

Tsuji, Chiho; Miyazawa, Etsuko; Sakamoto, Takeshi; Kikugawa, Yasuo

Synthetic Communications, 2002 , vol. 32, # 24 p. 3871 - 3879 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar Multi-step reaction with 2 steps 1: triethylamine / acetonitrile / 2 h 2: POCl3 / acetonitrile / 3 h / Heating View Scheme

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Rx-ID: 14737467 Find similar reactions

Janin, Yves L.; Roulland, Emmanuel; Beurdeley-Thomas, Arnaud; Decaudin, Didier; Monneret, Claude; Poupon, Marie-France

Journal of the Chemical Society. Perkin Transactions 1, 2002 , # 4 p. 529 - 532 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 8878782 Find similar reactions

82%

With sodium hydrogensulfite; sodium nitrite in ethanol; water; acetic acid

T=24°C; 4 h;

Geoffroy, Otto J.; Morinelli, Thomas A.; Meier, G. Patrick

Tetrahedron Letters, 2001 , vol. 42, # 32 p. 5367 - 5369 Title/Abstract Full Text View citing articles Show Details

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With aluminum oxide; Oxonereg;

0.1 h; microwave irradiation;

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Rx-ID: 8681260 Find similar reactions

Ramalingam; Subba Reddy; Srinivas; Yadav

Synthetic Communications, 2000 , vol. 30, # 24 p. 4507 - 4512 Title/Abstract Full Text View citing articles Show Details

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With toluene-4-sulfonic acid in toluene

Elimination; 0.5 h; Heating;

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Rx-ID: 5294602 Find similar reactions

Coskun, Necdet; Arikan, Nevin

Tetrahedron, 1999 , vol. 55, # 40 p. 11943 - 11948 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar Multi-step reaction with 2 steps 1: 95 percent / ethanol / 1 h / 20 °C 2: 93 percent / TsOH*H2O / toluene / 0.5 h / Heating View Scheme

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Rx-ID: 16146157 Find similar reactions

Coskun, Necdet; Arikan, Nevin

Tetrahedron, 1999 , vol. 55, # 40 p. 11943 - 11948 Title/Abstract Full Text View citing articles Show Details

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Hide Experimental Procedure

Rx-ID: 24679388 Find similar reactions

Hoechst Aktiengesellschaft

Patent: US5756804 A1, 1998 ; Title/Abstract Full Text Show Details

47:Cross-coupling of 2-chlorobenzonitrile with 4-tolueneboronic acid

Example 47 Cross-coupling of 2-chlorobenzonitrile with 4-tolueneboronic acid To prepare the catalyst, 38.8 mg (0.219 mmol) of palladium(II) chloride and 54.0 mg (0.657 mmol) of sodium acetate are stirred for 30 minutes at 23° C. in 2.4 ml of DMSO under an argon atmosphere. Subsequently, 1.99 ml (0.875 mmol) of a 0.44 molar aqueous solution of sodium 4-diphenylphosphinophenylphosphinate, prepared as described below, are added and the suspension is stirred for a further 30 minutes at 23° C. Under an argon atmosphere, 30.0 g (0.2181 mol) of 2-chlorobenzonitrile, 32.6 g (0.240 mol) of 4-tolueneboronic acid and 16.2 g (70 mol percent) of sodium carbonate are stirred into 120 ml of ethylene glycol. 20 ml of water are added and the mixture is heated to 80° C. The above-described catalyst suspension is then added and the mixture is heated for 5 hours under reflux. At 23° C., the mixture is admixed with 100 ml of ethyl acetate. The organic phase is separated off, evaporated on a rotary evaporator and fractionally distilled under reduced pressure. This gives 31.6 g (75percent of theory) of 2-cyano-4'-methylbiphenyl (bp. 140° C./1.0 mbar; mp. 50° C.). A

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Rx-ID: 4739457 Find similar reactions

A: 6 % Chromat. B: 47% C: 17%

With ammonium cerium(IV) nitrate

T=70°C; 1 h;

Giurg; Mlochowski

Polish Journal of Chemistry, 1997 , vol. 71, # 8 p. 1093 - 1101 Title/Abstract Full Text View citing articles Show Details

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With (C2H5)3NH2CO2; palladium on activated charcoal in acetonitrile

T=80°C; Yield given;

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Pews; Hunter; Wehrmeyer

Tetrahedron, 1993 , vol. 49, # 22 p. 4809 - 4820 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 8427951 Find similar reactions

C: 38%

in xylene

5 h; Heating;

Wai, Kwok-Fai; Sammes, Michael P.

Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1991 , # 1 p. 183 - 187 Title/Abstract Full Text View citing articles Show Details

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Synthesize Find similar Rx-ID: 8427965 Find similar reactions

B: 25%

in xylene

4 h; Heating;

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Wai, Kwok-Fai; Sammes, Michael P.

Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1991 , # 1 p. 183 - 187 Title/Abstract Full Text View citing articles Show Details

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With CuCl-alumina in various solvent(s) T=150°C; 6 h;

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Rx-ID: 3962056 Find similar reactions

Clark, James H.; Jones, Craig W.; Duke, Catherine V. A.; Miller, Jack M.

Journal of Chemical Research, Miniprint, 1989 , # 8 p. 1745 - 1758 Title/Abstract Full Text Show Details

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1.) DMF, r.t., 3 min; 2.) CH3CN, r.t.; Yield given. Multistep reaction;

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Rx-ID: 6520244 Find similar reactions

Sutherland, Ronald G.; Zhang, Chun-Hao; Piorko, Adam; Lee, Choi Chuck

Canadian Journal of Chemistry, 1989 , vol. 67, p. 137 - 142 Title/Abstract Full Text Show Details

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Synthesize Find similar Rx-ID: 3394699 Find similar reactions

With NiBr2(PPh3)2 in N,N,N',N',N'',N''hexamethylphosphoric triamide

T=60°C; 16 h;

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Sakakibara, Yasumasa; Okuda, Fumio; Shimobayashi, Akira; Kirini, Kunihiko; Sakai, Mutsuji; et al.

Bulletin of the Chemical Society of Japan, 1988 , vol. 61, p. 1985 - 1990 Title/Abstract Full Text Show Details

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Rx-ID: 2958489 Find similar reactions

98%

With polystyrene-bound diaryl telluroxide in dichloromethane

1 h; Ambient temperature;

Hu, Nan Xing; Aso, Yoshio; Otsubo, Tetsuo; Ogura, Fumio

Bulletin of the Chemical Society of Japan, 1986 , vol. 59, # 3 p. 879 - 884 Title/Abstract Full Text Show Details

95%

With polystyrne-bound selenoxide in ethanol

24 h; Heating;

Hu, Nan Xing; Aso, Yoshio; Otsubo, Tetsuo; Ogura, Fumio

Chemistry Letters, 1985 , p. 603 - 606 Title/Abstract Full Text Show Details

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Rx-ID: 3795546 Find similar reactions

88%

With triethylamine in dichloromethane

1 h; Ambient temperature;

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Saednya, Akbar

Synthesis, 1983 , # 9 p. 748 - 749 Title/Abstract Full Text Show Details

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Synthesize Find similar Rx-ID: 2603352 Find similar reactions

B: 21.7% C: 27%

in pyridine

1 h; Heatingother temp. and time; Product

Yamazaki, Chiji

Journal of Organic Chemistry, 1981 , vol. 46, # 20 p. 3956 - 3959

distributionMechanism;

Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 3377264 Find similar reactions

gaseous plasma of glow discharge; Yield given. Further byproducts given. Yields of byproduct given;

So, Y. H.; Miller, Larry L.

Journal of the American Chemical Society, 1981 , vol. 103, # 14 p. 4204 - 4209 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 3377265 Find similar reactions

A: 17 % Chromat. B: 17 % Chromat. D: 19 % Chromat. E: 20 % Chromat.

plasma apparatus; a variety of substituted benzenes and pyridine similarly cyanated; Product distribution;

So, Ying-Hung; Miller, Larry L.

Journal of the American Chemical Society, 1980 , vol. 102, # 23 p. 7119 - 7120 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 721001 Find similar reactions

With sulfuric acid; sodium nitrite

Eintragen der erhaltenen Diazoniumsalz-Loesung in eine aus Natriumcyanid und Kupfer(I)-cyanid in Wasser bereitete Loesung bei 70-80grad;

Hodgson; Heyworth

Journal of the Chemical Society, 1949 , p. 1131 Full Text View citing articles Show Details

With sulfuric acid; sodium nitrite

Eintragen der erhaltenen Diazoniumsalz-Loesung in eine aus Kaliumcyanid und Kupfer(I)-cyanid in Wasser bereitete Loesung bei 30-40grad;

Hodgson; Heyworth

Journal of the Chemical Society, 1949 , p. 1131 Full Text View citing articles Show Details

Diazotization.Behandlung der Diazoloesung mit Kaliumkupfercyanuerloesung;

Montagne

Recueil des Travaux Chimiques des Pays-Bas, 1900 , vol. 19, p. 55 Full Text Show Details

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Rx-ID: 6076175 Find similar reactions

T=700 - 750°C;

Farbenfabr. Bayer

Patent: DE842045 , 1948 ; DRP/DRBP Org.Chem. Full Text Show Details

T=800°C;

Farbenfabr. Bayer

Patent: DE842045 , 1948 ; DRP/DRBP Org.Chem. Full Text Show Details

Synthesize Find similar T=250°C; Einleiten von Chlorcyan;

Rx-ID: 6520250 Find similar reactions

Zappi; Bouso

Anales de la Asociacion Quimica Argentina (1921-2001), 1947 , vol. 35, p. 137 Chem.Abstr., 1948 , p. 7704 Full Text Show Details

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Rx-ID: 171807 Find similar reactions

T=-45°C;

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Le Maistre; Rainsford; Hauser

Journal of Organic Chemistry, 1939 , vol. 4, p. 106,107, 109 Full Text View citing articles Show Details

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Rx-ID: 6520247 Find similar reactions

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Stephenson; Waters

Journal of the Chemical Society, 1939 , p. 1796,1802 Full Text View citing articles Show Details

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Rx-ID: 6674980 Find similar reactions

Stephenson; Waters

Journal of the Chemical Society, 1939 , p. 1796,1802 Full Text View citing articles Show Details

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Rx-ID: 6682791 Find similar reactions

Stephenson; Waters

Journal of the Chemical Society, 1939 , p. 1796,1802 Full Text View citing articles Show Details

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Rx-ID: 6682792 Find similar reactions

Stephenson; Waters

Journal of the Chemical Society, 1939 , p. 1796,1802 Full Text View citing articles Show Details

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Rx-ID: 6682914 Find similar reactions

Stephenson; Waters

Journal of the Chemical Society, 1939 , p. 1796,1802 Full Text View citing articles Show Details

Synthesize Find similar With quinoline; copper(I) bromide

T=200°C;

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Rx-ID: 6520246 Find similar reactions

Gen. Aniline and Film Co.

Patent: US2195076 , 1937 ; Full Text Show Details

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Rx-ID: 60815 Find similar reactions

T=0°C; Kinetics;

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Hauser; Le Maistre; Rainsford

Journal of the American Chemical Society, 1935 , vol. 57, p. 1056,1058 Full Text View citing articles Show Details

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Synthesize Find similar Rx-ID: 441645 Find similar reactions

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Brady; McHugh

Journal of the Chemical Society, 1923 , vol. 123, p. 1198 Full Text View citing articles Show Details

Hauser; Jordan; O'Connor

Journal of the American Chemical Society, 1935 , vol. 57, p. 2456 Full Text View citing articles Show Details

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Rx-ID: 455230 Find similar reactions

With sodium ethanolate

Hauser; Gillaspie

Journal of the American Chemical Society, 1930 , vol. 52, p. 4517 Full Text View citing articles Show Details

With potassium hydroxide

Hauser; Gillaspie

Journal of the American Chemical Society, 1930 , vol. 52, p. 4517 Full Text View citing articles Show Details

T=275°C;

Hauser; Hauser

Journal of the American Chemical Society, 1930 , vol. 52, p. 2050,2052 Full Text View citing articles Show Details

Hauser; Gillaspie; Le Maistre

Journal of the American Chemical Society, 1935 , vol. 57, p. 567 Full Text View citing articles Show Details

T=30°C; Aufbewahren im Exsiccator ueber NaOH;

Hauser; Hauser; Gillaspie

Journal of the American Chemical Society, 1930 , vol. 52, p. 4158,4161 Full Text View citing articles Show Details

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Rx-ID: 7977301 Find similar reactions

T=0°C; Kinetics;

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Hauser; Le Maistre; Rainsford

Journal of the American Chemical Society, 1935 , vol. 57, p. 1056,1058 Full Text View citing articles Show Details

Synthesize Find similar T=215°C; Thermolysis;

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Rx-ID: 7998592 Find similar reactions

Hauser; Hauser

Journal of the American Chemical Society, 1930 , vol. 52, p. 2050,2052 Full Text View citing articles Show Details

Hauser; Gillaspie; Le Maistre

Journal of the American Chemical Society, 1935 , vol. 57, p. 567 Full Text View citing articles Show Details

Hauser; Hauser; Gillaspie

Journal of the American Chemical Society, 1930 , vol. 52, p. 4158,4161 Full Text View citing articles Show Details

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Synthesize Find similar Rx-ID: 8264265 Find similar reactions

T=100°C;

Hauser; Jordan; O'Connor

Journal of the American Chemical Society, 1935 , vol. 57, p. 2456 Full Text View citing articles Show Details

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Synthesize Find similar Rx-ID: 7543799 Find similar reactions

Bei der Destillation unter Normaldruck;

Howard et al.

Journal of the American Chemical Society, 1932 , vol. 54, p. 3628,3635 Full Text View citing articles Show Details

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Rx-ID: 192135 Find similar reactions

T=0°C;

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Hauser; Gillaspie

Journal of the American Chemical Society, 1930 , vol. 52, p. 4517 Full Text View citing articles Show Details

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Rx-ID: 7977302 Find similar reactions

T=0°C;

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Hauser; Gillaspie

Journal of the American Chemical Society, 1930 , vol. 52, p. 4517 Full Text View citing articles Show Details

Synthesize Find similar T=200 - 210°C;

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Rx-ID: 6520245 Find similar reactions

I.G. Farbenind. Patent: DE524715 , 1929 ; Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 18, p. 438 Full Text Show Details

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Rx-ID: 6520249 Find similar reactions

Korczynski; Fandrich

Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1926 , vol. 183, p. 422 Full Text Show Details

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Rx-ID: 5802291 Find similar reactions

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Lander; Jewson

Journal of the Chemical Society, 1903 , vol. 83, p. 770 Full Text Show Details

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Rx-ID: 5436216 Find similar reactions

T=230°C;

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Maselli

Gazzetta Chimica Italiana, 1900 , vol. 30 II, p. 531 Full Text View citing articles Show Details

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Synthesize Find similar With hydrogenchloride; sodium nitrite

die Loesung mit Wasserdampf destillieren;

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Rx-ID: 6520248 Find similar reactions

Montagne

Recueil des Travaux Chimiques des Pays-Bas, 1900 , vol. 19, p. 55 Full Text Show Details

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Rx-ID: 7977303 Find similar reactions

Montagne

Recueil des Travaux Chimiques des Pays-Bas, 1900 , vol. 19, p. 55 Full Text Show Details

Synthesize Find similar With acetic anhydride

Einw. von Soda auf die Acetylverbindung;

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Rx-ID: 304550 Find similar reactions

Behrend; Nissen

Justus Liebigs Annalen der Chemie, 1892 , vol. 269, p. 396 Full Text View citing articles Show Details

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Rx-ID: 558717 Find similar reactions

Behandeln des Reaktionsprodukts mit Alkalien;

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Behrend; Nissen

Justus Liebigs Annalen der Chemie, 1892 , vol. 269, p. 396 Full Text View citing articles Show Details

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With phosphorus pentachloride

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Rx-ID: 495856 Find similar reactions

Henry

Chemische Berichte, 1869 , vol. 2, p. 492 Full Text View citing articles Show Details

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With phosphorus pentachloride

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Rx-ID: 782949 Find similar reactions

Henry

Chemische Berichte, 1869 , vol. 2, p. 492 Full Text View citing articles Show Details

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Rx-ID: 5436215 Find similar reactions

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Henry

Chemische Berichte, 1869 , vol. 2, p. 492 Full Text View citing articles Show Details

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Rx-ID: 5802290 Find similar reactions

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Henry

Chemische Berichte, 1869 , vol. 2, p. 492 Full Text View citing articles Show Details

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With phosphorus pentachloride

With tetraphosphorus decasulfide

Rx-ID: 6520243 Find similar reactions

Henry

Chemische Berichte, 1869 , vol. 2, p. 492 Full Text View citing articles Show Details

Henry

Chemische Berichte, 1869 , vol. 2, p. 492 Full Text View citing articles Show Details

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