2-Chloro-5-nitrobenzoyl chloride

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9 reactions in Reaxys

2017-06-15 08h:58m:52s (EST)

Cl

1. Query

O

O N Cl

O

Search as: As drawn

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Cl O

Cl

N OH

O

N Cl

O

Rx-ID: 273172 View in Reaxys 1/9 Yield 100%

Conditions & References 4 : 2-(2-Chloro-5-propionamidophenyl)-5-methylbenzooxazole (CT-116563) EXAMPLE 4 2-(2-Chloro-5-propionamidophenyl)-5-methylbenzooxazole (CT-116563) A mixture of 2-chloro-5-nitrobenzoic acid (7.06 g, 35.0 mmol) and thionyl chloride (35 ml) was heated at reflux for 2 h. Excess thionyl chloride was removed by distillation under reduced pressure to provide 2-chloro-5-nitrobenzoyl chloride (7.7 g, 100percent yield). With thionyl chloride Patent; CELL THERAPEUTICS, INC.; US2002/107269; (2002); (A1) English View in Reaxys

95%

1 : Production of 2-chloro-5-nitrobenzoyl chloride Example 1 Production of 2-chloro-5-nitrobenzoyl chloride To a 3 L 3 neck round bottom flask equipped with a mechanical stirrer, nitrogen inlet, reflux condenser, heating mantle, vacuum system, and scrubber system for efficient removal of HCl and SO2 gas which is liberated during the reaction, was charged, under nitrogen, 1.0 L (1.63 Kg, 13.7 moles) of thionyl chloride, and 1.3 Kg (6.4 moles) of 2chloro-5-nitrobenzoic acid. The stirred mixture was placed under a N2 flow, which was vented to the scrubber system. The stirred mixture was heated to reflux for 12 hours during which time the reaction slowly becomes complete. The clear yellow solution was placed under vacuum and excess thionyl chloride was removed by evaporation under vacuum. The resulting slurry was dissolved in 800 mL of toluene, and concentrated to dryness by evaporation under vacuum. The resulting yellow solid was dried at about 50° C. and about 20 mm Hg for about 4 hours to give 1.35 Kg of 2chloro-5-nitrobenzoyl chloride as a yellow solid (95percent yield). in toluene Patent; Scarborough, Robert; Kalaritis, Panos; Yiannikouros, George; Cruskie JR., Michel P.; Sha, Dezhi; US2005/4377; (2005); (A1) English View in Reaxys

93.1 %

With phosphorus pentachloride in benzene, Time= 3h, Heating Hayashi, Ikuo; Ogihara, Keizo; Shimizu, Kiyoshi; Bulletin of the Chemical Society of Japan; vol. 56; nb. 8; (1983); p. 2432 - 2437 View in Reaxys

92 %

With thionyl chloride, Time= 8h, T= 70 °C Srogl, Jiri; Hyvl, Jakub; Revesz, Agnes; Schroeder, Detlef; Chemical Communications; nb. 23; (2009); p. 3463 3465 View in Reaxys

91.7 %

53.a :a) Preparation of 2-chloro-N-(2,2-dimethoxy-ethyl)-5-nitro-benzamide. Thionyl chloride (14 mL, 192 mmol) was added'dropwise to a solution of 2- chloro-5-nitrobenzoic acid (10 g, 49.6 mmol) in chloroform (150 mL) at 0 0C. The mixture was heated to reflux for 4h then cooled to r.t, concentrated in vacuo and dried under high vacuum to yield 2chloro-5-nitrobenzoyl chloride (10 g, 91.7percent) as a solid. Under nitrogen, triethylamine (19 mL, 136 mmol) was added slowly to a solution of aminoacetaldehyde dimethyl acetal (5.43 mL, 50.0 mmol) in dry DCM (20 mL) at 0 °C. 2-Chloro-5-nitrobenzoyl chloride (10 g, 45.5 mmol) was slurried in dry DCM (30 mL) and added over a period of 30 minutes. The mixture was allowed to warm to r.t. and stirred overnight then partitioned between water and~DCM. The organic phase was washed with saturated sodium bicarbonate solution, water and brine then dried over sodium sulfate and concentrated. The crude product was triturated with petroleum ether then diethyl ether and finally purified by column chromatography on silica gel (60-120 mesh) eluting with ethyl acetate/petroleum ether (2percent to 40percent gradient) to afford 2-chloro-iV- (2,2-dimethoxy-ethyl)-5-nitro benzamide (8.3 g, 63percent) as a yellow solid.

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With thionyl chloride in chloroform, Time= 4h, T= 0 °C , Heating / reflux Patent; F2G LTD; WO2008/62182; (2008); (A1) English View in Reaxys 85 %

With phosphorus pentachloride in chlorobenzene, 1.) RT, 24 h, 2.) 50 deg C, 1 h Bellamy; Chazan; Dodey; Dutartre; Ou; Pascal; Robin; Journal of Medicinal Chemistry; vol. 34; nb. 5; (1991); p. 1545 - 1552 View in Reaxys With phosphorus pentachloride Montagne; Recueil des Travaux Chimiques des Pays-Bas; vol. 19; (1900); p. 55 View in Reaxys With thionyl chloride Dey; Doraiswami; Journal of the Indian Chemical Society; vol. 10; (1933); p. 353,357 View in Reaxys With thionyl chloride, Time= 3h, Heating Shinde; Shenoy; Pai; Indian Journal of Chemistry - Section B Organic Chemistry Including Medicinal Chemistry; vol. 29; nb. 8; (1990); p. 711 - 720 View in Reaxys Kumazawa, Eiji; Hirotani, Kenji; Burford, S. Clifford; Kawagoe, Keiichi; Miwa, Tamotsu; Mitsui, Ikuo; Ejima, Akio; Chemical and Pharmaceutical Bulletin; vol. 45; nb. 9; (1997); p. 1470 - 1474 View in Reaxys With thionyl chloride, Time= 1h, Heating Palmer, Brian D.; Wilson, William R.; Cliffe, Stephen; Denny, William A.; Journal of Medicinal Chemistry; vol. 35; nb. 17; (1992); p. 3214 - 3222 View in Reaxys With thionyl chloride in N,N-dimethyl-formamide, Heating Klunder, Janice M.; Hargrave, Karl D.; West, MaryAnn; Cullen, Ernest; Pal, Kollol; et al.; Journal of Medicinal Chemistry; vol. 35; nb. 10; (1992); p. 1887 - 1897 View in Reaxys With thionyl chloride, Time= 1.5h, Heating Pieper; Seydel; Kruger; Noll; Keck; Wiese; Arzneimittel-Forschung/Drug Research; vol. 39; nb. 9; (1989); p. 1073 - 1080 View in Reaxys With thionyl chloride in N,N-dimethyl-formamide Tercel; Denny; Wilson; Bioorganic and Medicinal Chemistry Letters; vol. 6; nb. 22; (1996); p. 2741 - 2744 View in Reaxys With oxalyl dichloride, N,N-dimethyl-formamide in dichloromethane, Ambient temperature Parlow, John J.; Mischke, Deborah A.; Woodard, Scott S.; Journal of Organic Chemistry; vol. 62; nb. 17; (1997); p. 5908 - 5919 View in Reaxys With thionyl chloride, N,N-dimethyl-formamide in 1,2-dichloro-ethane, Time= 14h, Heating Tercel, Moana; Denny, William A.; Journal of the Chemical Society - Perkin Transactions 1; nb. 3; (1998); p. 509 519 View in Reaxys With thionyl chloride in toluene

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Doelling, Wolfgang; Perjessy, Alexander; Schaller, Ingrid; Kolbe, Alfred; Journal of Heterocyclic Chemistry; vol. 35; nb. 1; (1998); p. 225 - 229 View in Reaxys With thionyl chloride Dolling, Wolfgang; Biedermann, Matthias; Hartung, Helmut; European Journal of Organic Chemistry; nb. 6; (1998); p. 1237 - 1242 View in Reaxys With phosphorus pentachloride, Chlorination Guirguis, Dalal B.; Egyptian Journal of Chemistry; vol. 42; nb. 1; (1999); p. 91 - 97 View in Reaxys With thionyl chloride in N,N-dimethyl-formamide, Time= 12h, Heating, Substitution Suna; Trapencieris; Chemistry of Heterocyclic Compounds; vol. 36; nb. 3; (2000); p. 287 - 300 View in Reaxys With thionyl chloride, N,N-dimethyl-formamide in chloroform, Heating Pilyugin; Sapozhnikov; Chikisheva; Kiseleva; Vorob'eva; Klimakova; Sapozhnikova; Kuznetsova; Russian Journal of General Chemistry; vol. 76; nb. 8; (2006); p. 1327 - 1330 View in Reaxys 1 : 2-Chloro-5-nitro-benzoyl chloride To a suspension of 2-chloro-5-nitro-benzoic acid (10 g, 49.6 mmol), oxalyl chloride was added dropwise (12.6 g, 2.0 equiv.). The resulting yellow solution was stirred at room temperature under argon overnight. The solvent was removed under vacuum to give a yellowish solid (10.8 g). With oxalyl dichloride, T= 20 °C Patent; Neuraxon Inc.; US6919328; (2005); (B1) English View in Reaxys R.24 : 2-Chloro-5-nitrobenzoyl chloride REFERENCE EXAMPLE 24 2-Chloro-5-nitrobenzoyl chloride As described for Reference Example 21, 5.0 g of 2-chloro-5-nitrobenzoic acid is reacted with 50 ml of thionyl chloride to give 5.6 g of the product as an off-white solid. With thionyl chloride Patent; American Cyanamid Company; US5532235; (1996); (A1) English View in Reaxys R.29 : 2-Chloro-5-nitrobenzoyl chloride REFERENCE EXAMPLE 29 2-Chloro-5-nitrobenzoyl chloride As described for Reference Example 26, 5.0 g of 2-chloro-5-nitrobenzoic acid is reacted with 50 ml of thionyl chloride to give 5.6 g of the product as an off-white solid. With thionyl chloride Patent; American Cyanamid Company; US5654297; (1997); (A1) English View in Reaxys R.24 : 2-Chloro-5-nitrobenzoyl chloride Reference Example 24 2-Chloro-5-nitrobenzoyl chloride As described for Reference Example 21, 5.0 g of 2-chloro-5-nitrobenzoic acid is reacted with 50 ml of thionyl chloride to give 5.6 g of the product as an off-white solid. With thionyl chloride

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Patent; American Cyanamid Company; US5719278; (1998); (A1) English View in Reaxys 28 :Intermediate 28: Ethyl (4-{[(2-chloro-5- nitrophenyl)carbonyl]amino}phenyl)acetate; 2-Chloro-5-nitrobenzoic acid (1.99g, 9.87mmol) was stirred for 18hrs at 6O0C in thionyl chloride (10ml). The excess thionyl chloride was removed by evaporation and the crude oil dissolved in chloroform (20ml). To this solution was added ethyl (4-aminophenyl)acetate (1.18g, 6.58mmol) and the reaction was stirred at 6O0C for 18hrs. The reaction was diluted with water and the phases separated. The organic layer was dried (Na2SO4), solvent evaporated and the residue <n="52"/>purified by flash chromatography (Biotage SP4, 40+M 0 --> 50percent ethylacetate / hexane) to afford the title compound as an off white solid (2.28g, 96percent). MS (ES+) m/z 363 [M+H+] (Ci7H15 35CIN2O5).1H-NMR (250MHz, CDCI3) δ 1.26 (3H, t, J 7), 3.62 (2H, s), 4.14 (2H, q, J 7), 7.30 (2H, d, J 8.5), 7.63 (3H, m), 7.93 (1 H, br s), 8.24 (1 H, dd, J 9, 3), 8.58 (1 H, d, J 3). With thionyl chloride, Time= 18h, T= 60 °C Patent; GLAXO GROUP LIMITED; WO2008/71736; (2008); (A1) English View in Reaxys 20.9 g

With thionyl chloride, Time= 8h, T= 70 °C Henke, Adam; Srogl, Jiri; Journal of Organic Chemistry; vol. 73; nb. 19; (2008); p. 7783 - 7784 View in Reaxys With pyridine, thionyl chloride, Time= 1.5h, Reflux Song, Dan-Qing; Wang, Yan; Wu, Lian-Zong; Yang, Peng; Wang, Yue-Ming; Gao, Li-Mei; Li, Yan; Qu, JingRong; Wang, Yong-Hong; Li, Ying-Hong; Du, Na-Na; Han, Yan-Xing; Zhang, Zhi-Ping; Jiang, Jian-Dong; Journal of Medicinal Chemistry; vol. 51; nb. 11; (2008); p. 3094 - 3103 View in Reaxys With thionyl chloride, Time= 2h, Reflux Kumar, Pradeep; Narasimhan, Balasubramanian; Sharma, Deepika; Judge, Vikramjeet; Narang, Rakesh; European Journal of Medicinal Chemistry; vol. 44; nb. 5; (2009); p. 1853 - 1863 View in Reaxys 77.A :A mixture of 2-chloro-5-nitrobenzoic acid (35 g), DMF (1 ml) and SOCl2 (430 ml) is heated under reflux for 2 h, concentrated in vacuo and added to the residue of MeOH keeping the temperature at 0° C. After stirring 18 h at AT and evaporation in vacuo, the residue is redissolved in DCM, the organic layer is washed with an aqueous NaOH solution then with an aqueous NaCl solution, and the organic layer is dried over MgSO4, filtered and evaporated to dryness. 37 g of desired product are obtained and used as such. With thionyl chloride, Time= 2h, Reflux Patent; CEREP; US2009/233910; (2009); (A1) English View in Reaxys With oxalyl dichloride, N,N-dimethyl-formamide in dichloromethane, Time= 2h, T= 0 - 20 °C Buettner, Anita; Seifert, Katrin; Cottin, Thomas; Sarli, Vasiliki; Tzagkaroulaki, Lito; Scholz, Stefan; Giannis, Athanassios; Bioorganic and Medicinal Chemistry; vol. 17; nb. 14; (2009); p. 4943 - 4954 View in Reaxys With thionyl chloride, Time= 3h, Reflux Xu, Ke-Ping; Zhang, Yuan-Yuan; Luo, Juan; Chen, Shan-Li; Wang, Yu-Liang; Journal of Chemical Research; nb. 6; (2010); p. 354 - 357 View in Reaxys 8 Preparation of (2-chloro-4-nitrophenyl)(p-tolyl)methanone (6a). Method B (using FeCl3): General procedure: 2-Chloro-4-nitrobenzoic acid (201 mg, 1.0 mmol) and cyanuric chloride (368 mg, 2 mmol) in 2 mL CH2Cl2 were treated with pyridine (79 mg, 1.0 mmol) and irradiated in the microwave for 15 min at 50 °C. Then, the resulting mixture was treated with FeCl3 (324 mg, 2.0 mmol) and irradiated in the microwave for 5 min at 30 °C. Finally, 3 mL of toluene was added to the solution and irradiated in the microwave for 15 min at 70 °C. Then the reaction mixture was filtered from Celite. The filtrate was washed with sodium thiosulphate followed by brine solution.

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The separated organic layer was dried on Na2SO4 and concentrated under reduced pressure to give pure product 6a (269.5 mg, 93percent yield). Mp 110-112 °C (lit. 1 111.2 °C). 1H NMR (500 MHz, CDCl3): δ 2.39 (s, 3H), 7.26 (d, J = 7.45 Hz, 2H), 7.54 (d, J = 7.45 Hz, 1H), 7.61 (d, J = 6.85 Hz, 2H), 8.26 (dd, J = 6.85, 2.7 Hz, 1H), 8.30 (d, J = 7.4 Hz, 1H); 13C NMR (500 Hz, CDCl3): δ 21.4 (CH3), 122.0 (CH), 125.1 (CH), 129.6 (CH), 129.7 (CH), 130.15 (CH), 132.2 (C), 144.6 (C), 146.2 (C), 148.9 (C), 193.5 (CO); IR (cm-1): 638.3, 740.8, 801.5, 836.3, 863.0, 1000.7, 1025.9, 1052.5, 1005.1, 1133.9, 1158.3, 1180.7, 1272.5, 1294.3, 1315.8, 1349.1, 1403.2, 1449.5, 1461.2, 1528.8, 1573.3, 1595.7, 1607.9, 1673.9, 3087.5; GC/MS: 275 [M+]; HRMS: calcd for C14H10ClNO3: 275.0349. Found: 275.0467. With pyridine, 1,3,5-trichloro-2,4,6-triazine in dichloromethane, Time= 0.25h, T= 50 °C , Microwave irradiation Mahdi, Jasia; Ankati, Haribabu; Gregory, Jill; Tenner, Brian; Biehl, Edward R.; Tetrahedron Letters; vol. 52; nb. 20; (2011); p. 2594 - 2596 View in Reaxys With thionyl chloride, Reflux Bhakuni, Bhagat Singh; Balkrishna, Shah Jaimin; Kumar, Amit; Kumar, Sangit; Tetrahedron Letters; vol. 53; nb. 11; (2012); p. 1354 - 1357 View in Reaxys With thionyl chloride, Reflux Balkrishna, Shah Jaimin; Kumar, Sangit; Synthesis; vol. 44; nb. 9; (2012); p. 1417 - 1426 View in Reaxys 1.b.1 :B) Synthesis of Compound 20; 1) Preparation of the Acid Chloride of Formula (III) (FIG. 1a); 2-Chloro-5-nitrobenzoic acid (6.04 g, 0.03 mol) is dissolved in 200 ml of dichloromethane. Oxalyl chloride (3.88 ml, 1.5 eq., 0.045 mol) is then added, followed, dropwise, by dimethylformamide (DMF), and the reaction medium is stirred for 3 hours. The solvent is then evaporated off so as to recover the acid chloride of formula (III). With oxalyl dichloride, N,N-dimethyl-formamide in dichloromethane, Time= 3h Patent; UNIVERSITE DE STRASBOURG; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE; US2012/196865; (2012); (A1) English View in Reaxys With thionyl chloride in dichloromethane, Time= 3h, Reflux Judge, Vikramjeet; Narasimhan, Balasubramanian; Ahuja, Munish; Sriram, Dharmarajan; Yogeeswari, Perumal; De Clercq, Erik; Pannecouque, Christophe; Balzarini, Jan; Medicinal Chemistry Research; vol. 21; nb. 7; (2012); p. 1451 - 1470 View in Reaxys With thionyl chloride, Reflux Saeed, Aamer; Hussain, Majid; Qasim, Muhammad; Turkish Journal of Chemistry; vol. 38; nb. 3; (2014); p. 436 442 View in Reaxys Reaction Steps: 2 1: thionyl chloride 2: thionyl chloride With thionyl chloride Veerareddy, Arava; Gogireddy, Surendrareddy; Dubey; Journal of Heterocyclic Chemistry; vol. 51; nb. 5; (2015); p. 1311 - 1321 View in Reaxys With pyridine, oxalyl dichloride in tetrahydrofuran, Time= 4h, T= 35 °C Sun, Chiyu; Li, Yangsheng; Shi, Ailong; Zhang, Jingzhou; Li, Yafei; Zhao, Mingming; Zhang, Lijuan; Zheng, Huachuan; Meng, Ying; Ding, Huaiwei; Song, Hongrui; MedChemComm; vol. 6; nb. 6; (2015); p. 1137 - 1142 View in Reaxys 4.2.1. Procedure A: Synthesis of an acyl chloride and coupling to an aniline derivative (Exemplified by 3)

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A catalytic amount of DMF was added to a stirred solution of 2-chloro-5-nitrobenzoic acid (2) (4.00 g, 19.85 mmol) and oxalyl chloride (8.65 mL, 99.19 mmol) in DCM (50 mL) at 0° C under nitrogen atmosphere. After 20 min, the reaction was allowed to warm to room temperature and to proceed for a further 2 h. The reaction mixture was concentrated, re-dissolved in DCM and concentrated again. Triethylamine (13.83 mL, 99.22 mmol) and p-toluidine (2.13 g, 19.85 mmol) were added to the crude product dissolved in DCM (50 mL). The reaction was stirred for 5 h at room temperature under nitrogen atmosphere. After completion, the reaction mixture was diluted with DCM and successively washed with HCl (aq., 1 M), NaHCO3 (aq., sat.), water and brine. The organic phase was dried over MgSO4, filtered, and concentrated to dryness. The crude amide was purified by column chromatography (SiO2, EtOAc/n-heptane, 7:3 / 9:1) to give 3 in 90percent yield With oxalyl dichloride, N,N-dimethyl-formamide in dichloromethane, Time= 2.33333h, T= 0 - 20 °C , Inert atmosphere Caraballo, Rémi; Larsson, Mikael; Nilsson, Stefan K.; Ericsson, Madelene; Qian, Weixing; Tran, Nam Phuong Nguyen; Kindahl, Tomas; Svensson, Richard; Saar, Valeria; Artursson, Per; Olivecrona, Gunilla; Enquist, Per-Anders; Elofsson, Mikael; European Journal of Medicinal Chemistry; vol. 103; (2015); p. 191 - 209 View in Reaxys 5-Amino-2-chloro-N-(1-cyanocyclopropyl)benzamide 3.20 g (15.9 mmol) of 2-chloro-5-nitrobenzoic acid are initially charged in 50 ml of dichloromethane p.a., and 0.06 ml of N,N-dimethylformamide p.a. is added. 2.08 ml (23.8 mmol) of oxalyl chloride are then added to the reaction mixture. After 3 h at RT, the reaction mixture is concentrated under reduced pressure on a rotary evaporator. The crude product (2-chloro-5-nitrobenzoyl chloride) is reacted further without further purification. With oxalyl dichloride, N,N-dimethyl-formamide in dichloromethane, Time= 3h, T= 20 °C Patent; BAYER INTELLECTUAL PROPERTY GMBH; Maue, Michael; Adelt, Isabelle; Heil, Markus; Jeschke, Peter; Kapferer, Tobias; Mühlthau, Friedrich August; Sudau, Alexander; Malsam, Olga; Lösel, Peter; Voerste, Arnd; Görgens, Ulrich; US9126945; (2015); (B2) English View in Reaxys 1; 1.a.i; A : Procedure A: Synthesis of an acyl chloride and coupling to an aniline derivative (Exemplified by 3) Procedure A: Synthesis of an acyl chloride and coupling to an aniline derivative (Exemplified by 3) A catalytic amount of DMF was added to a stirred solution of 2-chloro-5-nitrobenzoic acid (2) (4.00 g, 19.85 mmol) and oxalyl chloride (8.65 mL, 99.19 mmol) in DCM (50 mL) at 0°C under nitrogen atmosphere. After 20 min, the reaction was allowed to warm to room temperature and to proceed for a further 2 h. The reaction mixture was concentrated, redissolved in DCM and concentrated again. Triethylamine (13.83 mL, 99.22 mmol) and ^-toluidine (2.13 g, 19.85 mmol) were added to the crude product dissolved in DCM (50 mL). The reaction was stirred for 5 h at room temperature under nitrogen atmosphere. After completion, the reaction mixture was diluted with DCM and successively washed with HC1 (aq., 1M), NaHCCb (aq., sat.), water and brine. The organic phase was dried over MgSO/t, filtered, and concentrated to dryness. The crude amide was purified by column chromatography (S1O2, EtOAc/n-heptane, from 7:3 to 9: 1) to give 3 in 90percent yield. With oxalic acid, N,N-dimethyl-formamide in dichloromethane, Time= 2.33333h, T= 0 - 20 °C , Inert atmosphere Patent; LIPIGON PHARMACEUTICALS AB; CARABALLO, Rémi; ELOFSSON, Mikael; ENQUIST, Per-Anders; OLIVECRONA, Gunilla; NILSSON, Stefan; LARSSON, Mikael; WO2015/187082; (2015); (A1) English View in Reaxys With thionyl chloride, Inert atmosphere, Reflux Liebeskind, Lanny S.; Gangireddy, Pavankumar; Lindale, Matthew G.; Journal of the American Chemical Society; vol. 138; nb. 21; (2016); p. 6715 - 6718 View in Reaxys With thionyl chloride, N,N-dimethyl-formamide in ethyl acetate, Time= 6h, T= 60 - 65 °C , Inert atmosphere, Large scale Angelaud, Remy; Reynolds, Mark; Venkatramani, Cadapakam; Savage, Scott; Trafelet, Huldreich; Landmesser, Thomas; Demel, Peter; Levis, Michael; Ruha, Olivier; Rueckert, Baerbel; Jaeggi, Heinz; Organic Process Research and Development; vol. 20; nb. 8; (2016); p. 1509 - 1519 View in Reaxys With thionyl chloride in dichloromethane, Time= 2h, Reflux

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Liu, Gang; Xue, Ding; Yang, Jun; Wang, Juan; Liu, Xiaohua; Huang, Wenjing; Li, Jie; Long, Ya-Qiu; Tan, Wenfu; Zhang, Ao; Journal of Medicinal Chemistry; vol. 59; nb. 24; (2016); p. 11050 - 11068 View in Reaxys 1.1; 2.1 : (1) Preparation of 2-chloro-5-nitro-4'-ethoxybenzophenone Weigh 2-chloro-5-nitrobenzoic acid (2.06 g, 10 mmol) was dissolved in 5 mL of thionyl chloride, and 3 drops of pyridine was added dropwise,Stirring at 50 ° C for 3 hours, TLC tracking, raw material reaction is complete, stop the reaction. Remove the thionyl chloride by distillation under reduced pressureProcessed directly into the next reaction. With pyridine, thionyl chloride, Time= 3h, T= 50 °C , Concentration Patent; Jiangsu Zhengda Tianqing Pharmaceutical Industry Company Limited; Li, Baoli; Sun, Baoli; Wang, Lili; Zhang, Xiquan; Gu, Hongmei; Zhang, Yaling; (25 pag.); CN106279307; (2017); (A) Chinese View in Reaxys O O

O

Cl

N

O

N Cl

O

Rx-ID: 39953428 View in Reaxys 2/9 Yield

Conditions & References With thionyl chloride Veerareddy, Arava; Gogireddy, Surendrareddy; Dubey; Journal of Heterocyclic Chemistry; vol. 51; nb. 5; (2015); p. 1311 - 1321 View in Reaxys

Cl

O

Cl

O O

N

Cl

OH

O

N Cl

O

Rx-ID: 23916014 View in Reaxys 3/9 Yield

Conditions & References 43 : 5-[4-AMINO-6-(5-CHLORO-2-METHYLPHENYL)-[1,3,5]TRIAZIN-2-YLAMINO]-2-CHLORO-N-METHYLBENZAMIDE Example 43 5-[4-AMINO-6-(5-CHLORO-2-METHYLPHENYL)-[1,3,5]TRIAZIN-2-YLAMINO]-2-CHLORO-N-METHYLBENZAMIDE To a mixture of 2-chloro-5-nitrobenzoic acid (5.0 g, 25.0 mmol) and dichloromethane (100 ml) was added oxalyl chloride (2.7 ml, 31.0 mmol) followed by N,N-dimethylformamide (5 drops). After stirring for 2 hours, the mixture was concentrated under reduced pressure to provide 2-chloro-5-nitro-benzoyl chloride. in dichloromethane, N,N-dimethyl-formamide Patent; Cell Therapeutics, Inc.; US2003/153570; (2003); (A1) English View in Reaxys

Cl O

N Cl

O

Rx-ID: 7368263 View in Reaxys 4/9 Yield

Conditions & References PONCI; BARUFFINI; CROCI; GIALDI; Il Farmaco; edizione scientifica; vol. 18; (1963); p. 732 - 749 View in Reaxys Burdulene et al.; Lietuvos TSR Mokslu Akademijos Darbai, Serija B: Chemija, Technika, Fizine Geografija; vol. 4; (1973); p. 55,58; ; vol. 80; nb. 36800b; (1974) View in Reaxys

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Cl

Cl H 2N

N O

O

N Cl

O

Rx-ID: 21989030 View in Reaxys 5/9 Yield

Conditions & References Reaction Steps: 2 1: concentrated aqueous hydrochloric acid 2: thionyl chloride With hydrogenchloride, thionyl chloride Dey; Doraiswami; Journal of the Indian Chemical Society; vol. 10; (1933); p. 353,357 View in Reaxys

Cl

N

O

N Cl

O

Rx-ID: 21992322 View in Reaxys 6/9 Yield

Conditions & References Reaction Steps: 3 1: concentrated sulfuric acid 2: concentrated aqueous hydrochloric acid 3: thionyl chloride With hydrogenchloride, thionyl chloride, sulfuric acid Dey; Doraiswami; Journal of the Indian Chemical Society; vol. 10; (1933); p. 353,357 View in Reaxys

Cl

Cl O

N

N Cl

O

Rx-ID: 21990047 View in Reaxys 7/9 Yield

Conditions & References Reaction Steps: 3 1: diluted sulfuric acid 2: nitric acid 3: PCl5 With phosphorus pentachloride, sulfuric acid, nitric acid Montagne; Recueil des Travaux Chimiques des Pays-Bas; vol. 19; (1900); p. 55 View in Reaxys

Cl

H 2N

O

N

Cl

O

Rx-ID: 22025347 View in Reaxys 8/9 Yield

Conditions & References Reaction Steps: 4 1: hydrochloric acid; sodium nitrite / die Loesung mit Wasserdampf destillieren 2: diluted sulfuric acid 3: nitric acid 4: PCl5 With hydrogenchloride, phosphorus pentachloride, sulfuric acid, nitric acid, sodium nitrite Montagne; Recueil des Travaux Chimiques des Pays-Bas; vol. 19; (1900); p. 55 View in Reaxys

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Reaction Steps: 4 1: Diazotization.Behandlung der Diazoloesung mit Kaliumkupfercyanuerloesung 2: diluted sulfuric acid 3: nitric acid 4: PCl5 With phosphorus pentachloride, sulfuric acid, nitric acid Montagne; Recueil des Travaux Chimiques des Pays-Bas; vol. 19; (1900); p. 55 View in Reaxys

Cl

O

O HO

N Cl

O

Rx-ID: 22029336 View in Reaxys 9/9 Yield

Conditions & References Reaction Steps: 2 1: nitric acid 2: PCl5 With phosphorus pentachloride, nitric acid Montagne; Recueil des Travaux Chimiques des Pays-Bas; vol. 19; (1900); p. 55 View in Reaxys

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2017-06-15 08:59:37

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