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1
Synthesize Find similar 93.7%
Synthesize Find similar
Rx-ID: 646316 Find similar reactions
With N,N-dimethylformamide; trichlorophosphate
T=100°C;
Kaabak; Baranov; Kalitina; Orlov
Russian Journal of General Chemistry, 1998 , vol. 68, # 1 p. 117 - 119 Title/Abstract Full Text View citing articles Show Details
With phosphorus trichloride
Saenz de Buruaga
Anales de la Real Sociedad Espanola de Fisica y Quimica, 1929 , vol. 27, p. 712,714 Full Text View citing articles Show Details
With phosphorus pentachloride
Clark; Bell
Trans.roy.Soc.Canada, 1933 , vol. <3>27 III, p. 99,101 Chem. Zentralbl., 1934 , vol. 105, # I p. 1964 Full Text Show Details
With thionyl chloride
Kohlrausch; Pongratz
Zeitschrift fuer Physikalische Chemie, Abteilung B: Chemie der Elementarprozesse, Aufbau der Materie, 1933 , vol. 22, p. 382
Chemische Berichte, 1933 , vol. 66, p. 1357 Full Text View citing articles Show Details
Vogel
Journal of the Chemical Society, 1948 , p. 631 Full Text View citing articles Show Details
Galewski, Zbigniew
Molecular Crystals and Liquid Crystals (1969-1991), 1987 , vol. 151, p. 233 - 242 Title/Abstract Full Text Show Details
With phosphorus pentachloride
Roberts et al.
Journal of the American Chemical Society, 1950 , vol. 72, p. 4237,4242 Org.Synth.Isotopes, 1958 , p. 378 Full Text View citing articles Show Details
With phosphorus trichloride
Aschan
Chemische Berichte, 1898 , vol. 31, p. 2346 Full Text View citing articles Show Details
Michael
Chemische Berichte, 1901 , vol. 34, p. 4044 Full Text View citing articles Show Details
Linnemann
Justus Liebigs Annalen der Chemie, 1868 , vol. 148, p. 257 Justus Liebigs Annalen der Chemie, 1872 , vol. 161, p. 18 Full Text View citing articles Show Details
With disulfur dichloride; chlorine
Read
Journal of the American Chemical Society, 1922 , vol. 44, p. 1753 Full Text View citing articles Show Details
With tetrachlorosilane; xylene
T=50°C;
Montonna
Journal of the American Chemical Society, 1927 , vol. 49, p. 2115 Full Text View citing articles Show Details
With hydrogenchloride; acetonitrile
T=0°C;
Colson
Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1895 , vol. 121, p. 1155 Annales de Chimie (Cachan, France), 1897 , vol. <7>12, p. 250 Full Text View citing articles Show Details
With thionyl chloride in tetrachloromethane
T=65°C;
Katritzky, Alan R.; Cutler, Alan T.; Dennis, Nicolas; Sabongi, Gebran J.; Rahimi-Rastgoo, Soheila; et al.
Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980 , p. 1176 - 1184 Title/Abstract Full Text View citing articles Show Details
With thionyl chloride
Heating;
Boguslavskaya, L. S.; Morozova, T. V.
J. Appl. Chem. USSR (Engl. Transl.), 1992 , vol. 65, # 4.2 p. 881 - 886,716 - 720 Title/Abstract Full Text Show Details
With oxalyl dichloride in dichloromethane; N,N-dimethyl-formamide
Brown, Pamela; Davies, David T.; O'Hanlon, Peter J.; Wilson, Jennifer M.
Journal of Medicinal Chemistry, 1996 , vol. 39, # 2 p. 446 - 457 Title/Abstract Full Text View citing articles Show Details
With thionyl chloride in various solvent(s) T=60°C; activation energy (E); var. temp.; Rate constantKineticsThermodynamic data;
Boguslavskaya, L. S.; Morozova, T. V.
J. Appl. Chem. USSR (Engl. Transl.), 1992 , vol. 65, # 4.2 p. 881 - 886,716 - 720 Title/Abstract Full Text Show Details
With thionyl chloride
3 h; Heating;
Mannhold, Raimund; Cruciani, Gabriele; Weber, Horst; Lemoine, Horst; Derix, Andrea; Weichel, Claus; Clementi, Monica
Journal of Medicinal Chemistry, 1999 , vol. 42, # 6 p. 981 - 991 Title/Abstract Full Text View citing articles Show Details
With PS-Ph3P resin; trichloroacetonitrile in dichloromethane
T=20°C;
Buchstaller; Ebert; Anlauf
Synthetic Communications, 2001 , vol. 31, # 7 p. 1001 - 1005 Title/Abstract Full Text View citing articles Show Details
With thionyl chloride in dichloromethane
Briner, Karin; Collado, Ivan; Fisher, Matthew J.; Garcia-Paredes, Cristina; Husain, Saba; Kuklish, Steven L.; Mateo, Ana I.; O'Brien, Thomas P.; Ornstein, Paul L.; Zgombick, John; de Frutos, Oscar
Bioorganic and Medicinal Chemistry Letters, 2006 , vol. 16, # 13 p. 3449 - 3453 Title/Abstract Full Text View citing articles Show Details
With oxalyl dichloride in dichloromethane; N,N-dimethyl-formamide
Cummins, Ian; Landrum, Marie; Steel, Patrick G.; Edwards, Robert
Phytochemistry, 2007 , vol. 68, # 6 p. 811 - 818 Title/Abstract Full Text View citing articles Show Details
With thionyl chloride in benzene
6 h; Heating;
Kozlov; Basalaeva
Chemistry of Heterocyclic Compounds, 2006 , vol. 42, # 9 p. 1223 - 1228 Title/Abstract Full Text View citing articles Show Details
With thionyl chloride
4 h; Reflux;
Gong, Xiao-Wei; Li, Jin-Pei; Wu, Ji-Feng; Li, Xun; Zhai, Hai-Min; Feng, Bo; Xu, Wen-Fang; Tang, Wei
Journal of Chemical Research, 2008 , # 6 p. 327 - 330 Title/Abstract Full Text View citing articles Show Details
With thionyl chloride
T=85°C; 0.25 h;
Cottrell, Ian F.; Cowley, Andrew R.; Croft, Laura J.; Hymns, Lauren; Moloney, Mark G.; Nettleton, Ewan J.; Kirsty Smithies; Thompson, Amber L.
Tetrahedron, 2009 , vol. 65, # 12 p. 2537 - 2550 Title/Abstract Full Text View citing articles Show Details
With thionyl chloride
Reflux;
Sadygov; Alimardanov
Russian Journal of Organic Chemistry, 2009 , vol. 45, # 2 p. 166 - 172 Title/Abstract Full Text View citing articles Show Details
With oxalyl dichloride in dichloromethane
Altenkaemper, Mirko; Bechem, Benjamin; Perruchon, Johann; Heinrich, Swetlana; Maedel, Andrea; Ortmann, Regina; Dahse, Hans-Martin; Freunscht, Ellen; Wang, Yulin; Rath, Jennifer; Stich, August; Hitzler, Manuela; Chiba, Peter; Lanzer, Michael; Schlitzer, Martin
Bioorganic and Medicinal Chemistry, 2009 , vol. 17, # 22 p. 7690 - 7697 Title/Abstract Full Text View citing articles Show Details
With thionyl chloride
Reflux;
Dubey, Sonal; Jain, Vinod; Precthi
Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2009 , vol. 48, # 11 p. 1571 - 1576 Title/Abstract Full Text View citing articles Show Details
With thionyl chloride in ISOPROPYLAMIDE
T=0°C; Hide Experimental Procedure
PHARMACOSTECH CO., LTD.; KIM, Jae Won; CHA, Young Gwan; RYU, Hyung Chul; KIM, Sun Joo
Patent: WO2010/2075 A1, 2010 ; Location in patent: Page/Page column 25-26 ; Title/Abstract Full Text Show Details
11:
4-propionic acid (1.08 g, 1.1 equivalent ratio, Aldrich) was dissolved in 15 ml dimethylacetamide (DMAC, Aldrich) at 00C and then thionyl chloride (1.81 g, 1.15 equivalent ratio) was gradually added to the solution. After the mixture solution was stirred for 10 min at 00C, the mixture of l-(3-amino-2-hydroxy-phenyl)-ethanone (2 g, 1 equivalent ratio) dissolved in 15 ml dimethylacetamide (DMAC, Aldrich) was slowly added to the mixture solution, and thermally stirred for 5 hrs at 25°C. The reaction mixture was mixed with 40 ml H2O and stirred for 1 hr at 25°C. The solid material obtained by filtering the solid material produced was washed with 20 ml H2O and then dried at 600C with hot-wind, obtaining 2.60 g (yield rate: 95percent): 1H NMR (300 MHz, DMSO) δ 12.70 (bs, IH) 9.26 (bs, IH) 8.16 (d, IH, J = 7.68 Hz) 7.68 (d, IH, J = 6.78 Hz) 6.94 (t, IH, 7= 8.04 Hz) 2.66 (s, 3H) 2.42 (q, 2H, J= 7.5 Hz) 1.07 (t, 3H, J = 7.5 Hz). With oxalyl dichloride
Wasa, Masayuki; Yu, Jin-Quan
Tetrahedron, 2010 , vol. 66, # 26 p. 4811 - 4815 Title/Abstract Full Text View citing articles Show Details
With oxalyl dichloride; N,N-dimethylformamide in dichloromethane
T=0 - 20°C; Hide Experimental Procedure
GLAXOSMITHKLINE LLC; AXTEN, Jeffrey, Michael; BRADY, Gerald, Patrick, Jr.; GALLAGHER, Timothy, Francis; HEERDING, Dirk, A.; MEDINA, Jesus, Raul; ROMERIL, Stuart, Paul
Patent: WO2010/120854 A1, 2010 ; Location in patent: Page/Page column 120-121 ; Title/Abstract Full Text Show Details
To a solution of propionic acid (10.0 g, 135.0 mmol) and DMF (0.1 ml.) in CH2CI2 (100 ml.) was added oxalyl chloride (25.7 g, 202.5 mmol) dropwise slowly at 0 0C. The reaction mixture was then stirred at ambient temperature for 2 hours, and distilled in vacuo to afford propionyl chloride (6.98 g) as a colorless liquid. With trichloroacetonitrile; triphenylphosphine in acetonitrile
T=20°C; Inert atmosphere;
Kim, Joong-Gon; Jang, Doo Ok
Synlett, 2010 , # 20 art. no. U08710ST, p. 3049 - 3052 Title/Abstract Full Text View citing articles Show Details
With oxalyl dichloride; N,N-dimethylformamide in dichloromethane
T=20°C; 0.5 h;
Dos Santos, Aurelie; El Kaim, Laurent; Grimaud, Laurence; Ronsseray, Caroline
European Journal of Organic Chemistry, 2011 , # 17 p. 3117 - 3121 Title/Abstract Full Text View citing articles Show Details
With thionyl chloride in dichloromethane
Angeles-Lopez, Guadalupe; Perez-Vasquez, Araceli; Hernandez-Luis, Francisco; Deciga-Campos, Myrna; Bye, Robert; Linares, Edelmira; Mata, Rachel
Journal of Ethnopharmacology, 2010 , vol. 131, # 2 p. 425 - 432 Title/Abstract Full Text View citing articles Show Details
1 h; Reflux;
With thionyl chloride
Wang, Zhixin; Chen, Ning; Xu, Jiaxi
Tetrahedron, 2011 , vol. 67, # 50 p. 9690 - 9699 Title/Abstract Full Text View citing articles Show Details
With thionyl chloride
T=60°C; 3.5 h;
Seashore-Ludlow, Brinton; Villo, Piret; Somfai, Peter
Chemistry - A European Journal, 2012 , vol. 18, # 23 p. 7219 - 7223 Title/Abstract Full Text View citing articles Show Details
With thionyl chloride
T=20 - 80°C; 3.66667 h;
Singh, Manjeet; Kumar, Sunil; Kumar, Ashwani; Kumar, Pradeep; Narasimhan, Balasubramanian
Medicinal Chemistry Research, 2012 , vol. 21, # 4 p. 511 - 522 Title/Abstract Full Text View citing articles Show Details
With thionyl chloride
2 h; Heating;
Yanvarev; Korovina; Usanov; Kochetkov
Russian Journal of Bioorganic Chemistry, 2012 , vol. 38, # 2 p. 224 - 229 Title/Abstract Full Text View citing articles Show Details
With bis(trichloromethyl) carbonate
T=40°C; 3 h;
Lin, Qi; Zhang, You-Ming; Li, Man-Lin; Wei, Tai-Bao
Synthetic Communications, 2012 , vol. 42, # 22 p. 3251 - 3260 Title/Abstract Full Text View citing articles Show Details
With oxalyl dichloride in dichloromethane
3 h; Hide Experimental Procedure
Delpiccolo, Carina M.L.; Testero, Sebastian A.; Leyes, Federico N.; Boggian, Dora B.; Camacho, Cristian M.; Mata, Ernesto G.
Tetrahedron, 2012 , vol. 68, # 52 p. 10780 - 10786 Title/Abstract Full Text View citing articles Show Details
Preparation of 4a:
General procedure: A solution of 5-phenylvaleric acid (12a) (0.053 g, 0.3 mmol, 4 equiv) and oxalyl chloride (0.040 mL, 0.45 mmol) were stirred in anhydrous dichloromethane (1.9 mL) for 3 h, and then the mixture was evaporated in vacuo to afford the crude 5-phenylvaleroyl chloride (4a), which was used without further purification.#10; With thionyl chloride
Ge, Hai-Xia; Zhang, Jian; Chen, Ling; Kou, Jun-Ping; Yu, Bo-Yang
Bioorganic and Medicinal Chemistry, 2013 , vol. 21, # 1 p. 62 - 69 Title/Abstract Full Text View citing articles Show Details
With oxalyl dichloride; N,N-dimethylformamide in dichloromethane
T=0 - 20°C; 1.5 h; Hide Experimental Procedure
GLENMARK PHARMACEUTICALS S.A.; CHAUDHARI, Sachin Sundarlal; THOMAS, Abraham; ADIK, Bharat Gangadhar; DHONE, Sachin Vasantrao; WADEKAR, Prashant Dilip; KHAIRATKAR-JOSHI, Neelima; SHAH, Daisy Manish
Patent: WO2013/24427 A1, 2013 ; Location in patent: Page/Page column 37; 38 ; Title/Abstract Full Text Show Details
1:
Alternatively, N-(4-fluoro-3-nitrophenyl)propanamide can be prepared by the procedure described below. To a well stirred solution of propanoic acid (1 equiv.) in dry dichloro methane was added catalytic amount of anhydrous DMF followed by oxalyl chloride (2 equiv.) and the reaction mixture was stirred at 0 °C for 30 min and then at room temperature for 1 h. The solvent was evaporated under reduced pressure and the residue obtained was dissolved in anhydrous dichloromethane. The reaction mixture was cooled to 0 °C and a solution of 4-fluoro-3-nitroaniline (1 equiv.) in dichloromethane was added to it, followed addition of triethylamine (2.5 equiv.). The reaction mixture was stirred at room temperature for overnight. The reaction mixture was extracted with ethyl acetate and washed with IN hydrochloric acid, bicarbonate solution, brine, dried over Na2SO4 and concentrated under reduced pressure. The crude residue was purified by column chromatography to yield N(4-fluoro-3- nitrophenyl)propanamide as a yellow solid. With thionyl chloride
T=85°C; 3 h; Inert atmosphere;
Shang, Rui; Ilies, Laurean; Matsumoto, Arimasa; Nakamura, Eiichi
Journal of the American Chemical Society, 2013 , vol. 135, # 16 p. 6030 - 6032 Title/Abstract Full Text View citing articles Show Details
With oxalyl dichloride in dichloromethane; N,N-dimethyl-formamide
Pierrat, Philippe; Kereselidze, Dimitri; Wehrung, Patrick; Zuber, Guy; Pons, Francoise; Lebeau, Luc
Pharmaceutical Research, 2013 , vol. 30, # 5 p. 1362 - 1379 Title/Abstract Full Text View citing articles Show Details
T=20°C; 1 h;
With oxalyl dichloride; N,N-dimethylformamide in dichloromethane
T=23°C; 3 h;
Cherney, Alan H.; Kadunce, Nathaniel T.; Reisman, Sarah E.
Journal of the American Chemical Society, 2013 , vol. 135, # 20 p. 7442 - 7445 Title/Abstract Full Text View citing articles Show Details
With thionyl chloride; N,N-dimethylformamide in dichloromethane
T=0 - 20°C; 2.33333 h;
Kobeissi, Marwan; Cherry, Khalil; Jomaa, Wissam
Synthetic Communications, 2013 , vol. 43, # 21 p. 2955 - 2965 Title/Abstract Full Text View citing articles Show Details
With thionyl chloride in N,N-dimethylformamide
T=70°C; 1.5 h; Hide Experimental Procedure
Garcia-Barrantes, Pedro M.; Lamoureux, Guy V.; Perez, Alice L.; Garcia-Sanchez, Rory N.; Martinez, Antonio R.; San Feliciano, Arturo
European Journal of Medicinal Chemistry, 2013 , vol. 70, p. 548 - 557 Title/Abstract Full Text View citing articles Show Details
4.2 Synthesis of acyl chlorides
General procedure: To 5mL of previously distilled thionyl chloride were added 3mmol of the carboxylic acid, and immediately 3 drops of dimethylformamide (DMF). The reaction mixture was heated at 70°C for approximately 90min, forming a yellowish translucent solution. Excess of thionyl chloride was eliminated from the mixture with a rotary evaporator connected to a potassium hydroxide trap. Products obtained were pale yellow oils or solids. Acyl chlorides were employed directly for following reactions without further purification. With oxalyl dichloride in dichloromethane
Dhanya, Raveendra-Panickar; Sheffler, Douglas J.; Dahl, Russell; Davis, Melinda; Lee, Pooi San; Yang, Li; Nickols, Hilary Highfield; Cho, Hyekyung P.; Smith, Layton H.; D'Souza, Manoranjan S.; Conn, P. Jeffrey; Der-Avakian, Andre; Markou, Athina; Cosford, Nicholas D.P.
Journal of Medicinal Chemistry, 2014 , vol. 57, # 10 p. 4154 - 4172 Title/Abstract Full Text View citing articles Show Details
With thionyl chloride in N,N-dimethylformamide
T=70°C;
Shehzadi, Sumaira; Siddiqi, Humaira Masood; Qasim, Malik Muhammed; Fawad, Musfirah; Manan, Abdul; Khan, Naeema; Saleem, Samreen; Bashir, Farah; Mirza, Bushra
Journal of the Chemical Society of Pakistan, 2014 , vol. 36, # 3 p. 462 - 472 Title/Abstract Full Text View citing articles Show Details
With oxalyl dichloride in dichloromethane
T=20°C; 24 h; Inert atmosphere; Hide Experimental Procedure
Salama, Ismail; Löber, Stefan; Hübner, Harald; Gmeiner, Peter
Bioorganic and Medicinal Chemistry Letters, 2014 , vol. 24, # 16 p. 3753 - 3756 Title/Abstract Full Text View citing articles Show Details
General procedure for preparation of haloperidol esters 1 18
General procedure: The corresponding carboxylic or dicarboxylic acid (1.0 mmol) was dissolved in dry dichloromethane (5 ml) and oxalylchloride (0.17 ml, 2.0 mmol) was added under nitrogen atmosphere. The mixture was stirred for 24 hours at room temperature. After removing the solvent under reduced pressure, haloperidol(940 mg, 2.5 mmol), dichloromethane (10 ml) and DIPEA (0.41 ml, 2.5 mmol) were added. After being stirred for 19 hours at room temperature the reaction mixture was treated with water and extracted with dichloromethane. The organic layer was washed with NaHCO3 (saturated solution) and brine. After being dried over Na2SO4 the solvent was removed under reduced pressure to obtain the crude product. Purification was performed using flash chromatography with dichloromethane/methanol as a solvent system. With oxalyl dichloride in dichloromethane
T=0 - 20°C;
Zhu, Ru-Yi; He, Jian; Wang, Xiao-Chen; Yu, Jin-Quan
Journal of the American Chemical Society, 2014 , vol. 136, # 38 p. 13194 - 13197 Title/Abstract Full Text View citing articles Show Details
With oxalyl dichloride; N,N-dimethylformamide in dichloromethane
T=20°C; 2 h;
Damio, Mariana C. F. C. B.; Pasqualoto, Kerly F. M.; Ferreira, Adilson K.; Teixeira, Sarah F.; Azevedo, Ricardo A.; Barbuto, Jos A. M.; Palace-Berl, Fanny; Franchi-Junior, Gilberto C.; Nowill, Alexre E.; Tavares, Maurcio T.; Parise-Filho, Roberto
Archiv der Pharmazie, 2014 , vol. 347, # 12 p. 885 - 895 Title/Abstract Full Text View citing articles Show Details
With trichlorophosphate
T=-20°C;
Edfeldt, Fredrik; Evenäs, Johan; Lepistö, Matti; Ward, Alison; Petersen, Jens; Wissler, Lisa; Rohman, Mattias; Sivars, Ulf; Svensson, Karin; Perry, Matthew; Feierberg, Isabella; Zhou, Xiao-Hong; Hansson, Thomas; Narjes, Frank
Bioorganic and Medicinal Chemistry Letters, 2015 , vol. 25, # 12 art. no. 22648, p. 2496 - 2500 Title/Abstract Full Text View citing articles Show Details
With oxalyl dichloride; N,N-dimethylformamide in dichloromethane
T=20°C; Inert atmosphere;
Rao, Wei-Hao; Zhan, Bei-Bei; Chen, Kai; Ling, Peng-Xiang; Zhang, Zhuo-Zhuo; Shi, Bing-Feng
Organic Letters, 2015 , vol. 17, # 14 p. 3552 - 3555 Title/Abstract Full Text View citing articles Show Details
With oxalyl dichloride; N,N-dimethylformamide in dichloromethane
T=0 - 20°C; 3 h; Inert atmosphere; Hide Experimental Procedure
Kubo, Teruhiko; Aihara, Yoshinori; Chatani, Naoto
Chemistry Letters, 2015 , vol. 44, # 10 p. 1365 - 1367 Title/Abstract Full Text View citing articles Show Details
General Procedure for the Preparation of Starting Amide.
General procedure: To an oven-dried 100 mL three-necked flask, 4-phenylbutyric acid (1.6 g, 10 mmol), DMF (5drops) and DCM (20 mL) were added under a N2 atmosphere. Oxalyl chloride (1.0 mL, 12 mmol,1.2 equiv.) was added dropwise at 0 °C resulting in vigorous bubbling. The mixture was stirred for 3h at room temperature, and the solvent was then removed in vacuo. The resulting acid chloride wasused immediately without further purification. To a solution of acid chloride in DCM(30 mL), thesolution of 8-amino-5-chroloquinoline (2.1 g, 12 mmol, 1.2 equiv.), Et3N (2.5 mL, 24 mmol, 2equiv.) in DCM (15 mL) were added dropwise to the solution at 0 °C, and the solution was thenwarmed to room temperature. After stirring overnight, the reaction system was quenched with sat. aq.NaHCO3 (30 mL) and the organic layer was separated. The aqueous layer was extracted with DCM(2 x 15 mL). The combined organic layers were washed with 1 M HCl aq. (30 mL) and brine (30mL), dried over MgSO4, filtered and evaporated in vacuo. The resulting crude amide was purified bycolumn chromatography on silica gel (eluant: hexane/EtOAc = 4/1) to afford the desired amide as awhite solid (2.5 g, 77percent).
With oxalyl dichloride
Luo, Feihua; Yang, Jun; Li, Zhengkai; Xiang, Haifeng; Zhou, Xiangge
Advanced Synthesis and Catalysis, 2016 , vol. 358, # 6 p. 887 - 893 Title/Abstract Full Text View citing articles Show Details
With phosphorus trichloride
T=60 - 70°C; Hide Experimental Procedure
Mehton, Ramandeep K.; Meshram, Vineet; Saxena, Sanjai; Chhibber, Manmohan
Journal of the Brazilian Chemical Society, 2016 , vol. 27, # 7 p. 1236 - 1244 Title/Abstract Full Text View citing articles Show Details
Synthesis of compounds 3f1, 3f2 and 3f3
General procedure: The acid chloride was prepared from corresponding acid (0.5 mmol) and PCl3 (0.5 mmol) by heating and stirring at 60-70 °C till the evolution of hydrochloric acid gas ceased. The acid chloride thus prepared was added to a stirred solution of compound 2f (0.5 mmol), K2CO3 (0.3 mmol) in dicloromethane, DCM, (10 mL) at 0 °C. The reaction mixture was stirred for 2 h and quenched with water. The organic product was extracted with DCM (3 × 50 mL), dried over Na2SO4, and concentrated in vacuo. Crude product obtained was purified using silica column and solvent system (pet ether/ ethyl acetate, 70:30, v/v) to afford light brown solids. With thionyl chloride in dichloromethane 1 h; Reflux;
Dangroo, Nisar A.; Singh, Jasvinder; Gupta, Nidhi; Singh, Shashank; Kaul, Anapurna; Khuroo, Mohmmed A.; Sangwan, Payare L.
MedChemComm, 2017 , vol. 8, # 1 p. 211 - 219 Title/Abstract Full Text View citing articles Show Details
2
Synthesize Find similar With trichloroisocyanuric acid in dichloromethane
T=20°C; Inert atmosphere;
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Rx-ID: 44590313 Find similar reactions
Gaspa, Silvia; Amura, Ida; Porcheddu, Andrea; De Luca, Lidia
New Journal of Chemistry, 2017 , vol. 41, # 3 p. 931 - 939 Title/Abstract Full Text View citing articles Show Details
A
B
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3
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Rx-ID: 29483900 Find similar reactions
in chloroform-d1
0.25 h; Inert atmosphere;
Hardee, David J.; Kovalchuke, Lyudmila; Lambert, Tristan H.
Journal of the American Chemical Society, 2010 , vol. 132, # 14 p. 5002 - 5003 Title/Abstract Full Text View citing articles Show Details
A
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4
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With oxygen; chlorine
T=23.84°C; P=830 - 980 Torr; UVirradiation;
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A
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Kaiser; Wallington; Hurley
Journal of Physical Chemistry A, 2010 , vol. 114, # 1 p. 343 - 354 Title/Abstract Full Text View citing articles Show Details
5
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With oxygen; chlorine
T=236.84°C; P=700 - 950 Torr; UVirradiation;
Kaiser; Wallington; Hurley
Journal of Physical Chemistry A, 2010 , vol. 114, # 1 p. 343 - 354 Title/Abstract Full Text View citing articles Show Details
6
Synthesize Find similar Rx-ID: 29891793 Find similar reactions
With chlorine
T=23.84°C; P=830 - 980 Torr; UVirradiation;
Kaiser; Wallington; Hurley
Journal of Physical Chemistry A, 2010 , vol. 114, # 1 p. 343 - 354 Title/Abstract Full Text View citing articles Show Details
7
Synthesize Find similar 89%
Hide Experimental Procedure
Rx-ID: 5588916 Find similar reactions
Sumitomo Chemical Company, Limited
Patent: US4562281 A1, 1985 ; Title/Abstract Full Text Show Details
C.3:COMPARATIVE EXAMPLE 3 COMPARATIVE EXAMPLE 3 Propionyl chloride was obtained from propionic acid and benzoyl chloride according to the method described in J.A.C.S., 60, 1325 (1938). Yield, 89percent. Boiling point, 77°-78.5° C. To a 300-ml four-necked flask equipped with a thermometer, stirring apparatus and condenser were added 34.51 g (0.10 mole) of 2,2'-methylenebis(6-tert-butyl-4-methylphenol), 50 g of toluene and 11.13 g (0.11 mole) of triethylamine. After replacing the air in the container with nitrogen, 10.20 g (0.11 mole) of propionyl chloride was added dropwise. 55%
Hide Experimental Procedure
Pfizer Inc.
Patent: US6586430 B1, 2003 ; Title/Abstract Full Text Show Details
37:N-{(1S)-3-[3-endo-(1H-Benzimidazol-1-yl)-8-azabicyclo[3.2.1]oct-8-yl]-1-phenylpropyl}-1-propionyl-3-azetidinecarboxamide
EXAMPLE 37 N-{(1S)-3-[3-endo-(1H-Benzimidazol-1-yl)-8-azabicyclo[3.2.1]oct-8-yl]-1-phenylpropyl}-1-propionyl-3-azetidinecarboxamide The title compound was prepared from the title compound of preparation 73 and propionyl chloride using a similar procedure to that described in example 36 in 55percent yield. Found C, 70.19; H, 7.62; N, 13.60percent; C30H37N5O2;0.8H2O requires C, 70.09; H, 7.57; N, 13.62; 1H NMR (400 MHz, CDCl3): δ [ppm] 1.06-1.13 (3H, t), 1.60-1.68 (2H, m), 1.92-2.13 (8H, m), 2.29-2.39 (2H, m), 2.53-2.74 (2H, m), 3.18-3.32 (1H, m), 3.32-3.42 (2H, m), 4.05-4.23 (3H, m), 4.35-4.45 (1H, m), 4.66-4.76 (1H, m),
5.16-5.27 (1H, m), 6.84-6.94 and 7.06-7.13 (1H, m), 7.23-7.32 (5H, m), 7.32-7.44 (3H, m), 7.76-7.82 (1H, m), 8.03-8.06 (1H, m); LRMS: m/z 500.0 (MH+). Eilingsfeld et al.
Angewandte Chemie, 1960 , vol. 72, p. 836,837 Full Text Show Details
Atavin et al.
Zhurnal Organicheskoi Khimii, 1973 , vol. 9, p. 318,320 Full Text Show Details
Schmidt; Pichl
Chemische Berichte, 1965 , vol. 98, p. 1003 Full Text Show Details
Schmidt
Patent: DE1103913 ; Chem.Abstr., 1962 , vol. 56, # 2335 Full Text Show Details
Ogata; Matsuyama
Tetrahedron, 1970 , vol. 26, p. 5929,5936 Full Text Show Details
Fel'dman et al.
J. Appl. Chem. USSR (Engl. Transl.), 1962 , vol. 35, p. 1364,1309 Chem.Abstr., 1962 , vol. 57, # 11064 Full Text Show Details Lee Journal of the American Chemical Society, 1966 , vol. 88, p. 3440 Full Text View citing articles Show Details Dubchenko J. Appl. Chem. USSR (Engl. Transl.), 1973 , vol. 46, p. 1822,1933,1936 Full Text Show Details Rylski Acta Poloniae Pharmaceutica, 1962 , vol. 19, p. 447,448, 450 Chem.Abstr., 1964 , vol. 60, # 14466 Full Text View citing articles Show Details Brook et al. Canadian Journal of Chemistry, 1971 , vol. 49, p. 133 Full Text Show Details Matsuda et al. Hokkaido Daigaku Kogakubu Kenkyu Hokoku, 1978 , vol. 87, p. 151,152
Chem.Abstr., vol. 90, # 6055b Full Text Show Details
Matsuda et al.
Hokkaido Daigaku Kogakubu Kenkyu Hokoku, 1979 , vol. 95, p. 87,88 Chem.Abstr., vol. 92, # 76059 Full Text Show Details
Mamedow et al.
Azerbaidzhanskii Khimicheskii Zhurnal, 1964 , vol. 6, p. 25,27 Chem.Abstr., 1965 , vol. 63, # 11413 Full Text Show Details
Matsuda et al.
Nippon Kagaku Kaishi, 1974 , p. 198 Full Text Show Details
Monsanto
Patent: US3636102 , 1967 ; Chem.Abstr., 1972 , vol. 76, # 72049 Full Text Show Details
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Spagnol, Michel; Gilbert, Laurent; Le Govic, Anne-Marie
Patent: US2002/120169 A1, 2002 ; Title/Abstract Full Text Show Details
and 24, characterized in that the acylating agent is chosen from: acetic anhydride, ... benzoic anhydride, acetyl chloride, monochloroacetyl chloride, dichloroacetyl chloride, propanoyl chloride, isobutanoyl chloride, pivaloyl chloride, stearoyl chloride, ...
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Wyeth
Patent: US6479535 B1, 2002 ; Title/Abstract Full Text Show Details
di-Propionate of 1-[4-(2-Azepan-1-yl-ethoxy)-benzyl]-2-(4-hydroxy-phenyl)-3-methyl-1H-indol-5-ol (HCl) di-Propionate of 1-[4-(2-Azepan-1-yl-ethoxy)-benzyl]-2-(4-hydroxy-phenyl)-3-methyl-1H-indol-5-ol (HCl) Compound was prepared analogously to example No. 162 except the starting material used was example No. 98 and the acylating agent used was propionyl chloride: Mp=170.5-172° C.; CHN calcd for C36H42N2O5+HCl+0.75H2O; MS FAB 605 (M+Na)+.
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Chimie, Rhodia
Patent: US6608232 B1, 2003 ; Title/Abstract Full Text Show Details
A process according to claim 26, wherein the acylation agent is selected from the group consisting in: acetic anhydride; ... dichloroacetyl anhydride; acetyl chloride; monochloroacetyl chloride; dichloroacetyl chloride; propanoyl chloride; isobutanoyl chloride; pivaloyl chloride; stearoyl chloride; ...
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Chimie, Rhodia
Patent: US6608232 B1, 2003 ; Title/Abstract Full Text Show Details
Particular illustrative examples of acylation agents with formula (II) that can be cited are: acetic anhydride; ... dichloroacetyl anhydride; acetyl chloride; monochloroacetyl chloride; dichloroacetyl chloride; propanoyl chloride; isobutanoyl chloride; pivaloyl chloride; stearoyl chloride; ...
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American Home Products Corporation
Patent: US5998402 A1, 1999 ; Title/Abstract Full Text Show Details
Di-propionate of 1-[4-(2-Azepan-1-yl-ethoxy)-benzyl]-2-(4-hydroxy-phenyl)-3-methyl-1H-indol-5-ol) (HCl)
Di-propionate of 1-[4-(2-Azepan-1-yl-ethoxy)-benzyl]-2-(4-hydroxy-phenyl)-3-methyl-1H-indol-5-ol) (HCl) Compound was prepared analogously to example No. 162 except the starting material used was example No. 98 and the acylating agent used was propionyl chloride: Mp=170.5-172° C.; CHN calcd for C36 H42 N2 O5 +HCl+0.75 H2 O; MS FAB 605 (M+Na)+.
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Rhodia Chimie
Patent: US6013840 A1, 2000 ; Title/Abstract Full Text Show Details
Particular illustrative examples of acylation agents with formula (II) are: acetic anhydride; ... acetyl chloride; monochloroacetyl chloride; dichloroacetyl chloride; isobutanoyl chloride; propanoyl chloride; pivaloyl chloride; crotonyl chloride.
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Rhodia Chimie
Patent: US6013840 A1, 2000 ; Title/Abstract Full Text Show Details
A process according to claim 15, wherein the acylation agent is selected from the group consisting of: acetic anhydride; ... dichloroacetyl anhydride; acetyl chloride; monochloroacetyl chloride; dichloroacetyl chloride; propanoyl chloride; isobutanoyl chloride; pivaloyl chloride; and crotonyl chloride.
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Rhodia Chemie
Patent: US6121496 A1, 2000 ; Title/Abstract Full Text Show Details
Examples of acylating agents corresponding to formula (II) include, more particularly: acetic anhydride ... monochloroacetyl anhydride acetyl chloride monochloroacetyl chloride dichloroacetyl chloride propanoyl chloride isobutanoyl chloride pivaloyl chloride crotonyl chloride.
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Mitsui Toatsu Chemicals, Incorporated
Patent: US5232923 A1, 1993 ; Title/Abstract Full Text Show Details
20.2:(Compound No. 103)
(2) To a suspension of 1.49 g of L-proline methyl ester in 15 ml of chloroform, 3 g of triethylamine was added dropwise. The propionyl chloride obtained in (1) was dissolved in 7 ml of chloroform and added dropwise to the above mixture under ice cooling. The resultant mixture was allowed to stand overnight and heated to 50° C. with stirring for an hour. After cooling, the reaction mixture was poured into 10 ml of ice water.
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Rhone-Poulenc Chimie
Patent: US5637773 A1, 1997 ; Title/Abstract Full Text Show Details
Particularly exemplary acylation agents of formula (II) include: Acetyl chloride, Propanoyl chloride, Isobutanoyl chloride, Pivaloyl chloride,
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Rhone-Poulenc Chimie
Patent: US5817878 A1, 1998 ; Title/Abstract Full Text Show Details
Particular illustrative examples of acylation agents with formula (II) are: acetic anhydride; ... dichloroacetyl anhydride; acetyl chloride; monochloroacetyl chloride; dichloroacetyl chloride; propanoyl chloride; isobutanoyl chloride; pivaloyl chloride: crotonyl chloride.
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Rhone-Poulenc Chimie
Patent: US5817878 A1, 1998 ; Title/Abstract Full Text Show Details
A process according to claim 16, wherein the acylation agent is selected from the group consisting of: acetic anhydride; ... dichloroacetyl anhydride; acetyl chloride; monochloroacetyl chloride; dichloroacetyl chloride; propanoyl chloride; isobutanoyl chloride; pivaloyl chloride; and crotonyl chloride.
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Ciba-Geigy Corporation
Patent: US5120741 A1, 1992 ; Title/Abstract Full Text Show Details
1.5:1.5
1.5 Preparation of O-propionyl-N-(4-methyl-6-methoxymethylpyrimidin-2-yl)-3-fluorophenylhydroxylamine STR10 2.49 g (0.0095 mol) of N-(4-methyl-6-methoxymethylpyrimidin-2yl)-3-fluorophenylhydroxylamine and 1.5 g of triethylamine are dissolved in 30 ml of tetrahydrofuran, and the solution is treated dropwise with a solution of 1.16 g (0.0125 mol) of propionyl chloride in 10 ml of tetrahydrofuran at not more than 10° C. Triethylamine hydrochloride separates out. The mixture is extracted with water and chloroform and, after the solvents have been removed, 3.71 g of crude product are obtained which are purified by means of column chromatography. The pure yield is 1.99 g of oil (65.7percent of theory). For NMR data, see Table 2.
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Stauffer Chemical Company
Patent: US4613357 A1, 1986 ; Title/Abstract Full Text Show Details
3:Preparation of 2-[4-(5-trifluoromethyl-3-chloro-2-pyridyloxy)-phenoxy]-propionic acid, N,N-dimethylhydroxylamine ester
EXAMPLE 3 Preparation of 2-[4-(5-trifluoromethyl-3-chloro-2-pyridyloxy)-phenoxy]-propionic acid, N,N-dimethylhydroxylamine ester A round bottom flask was obtained and to this was added 7.4 grams (20 millimole) of 2-(4-[5-trifluoromethyl-3-chloro-2-pyridyloxy]-phenoxy) propionic acid slurried in 20 ml of ether under a nitrogen atmosphere. Thereafter 5 ml (68 millimoles) of thionyl chloride was added thereto, dropwise. The reactants were heated to reflux temperature and maintained at reflux for approximately 11/2 hours. The reactants were then stirred overnight at room temperature and concentrated on a rotovac, yielding 7.6 grams of the corresponding propionyl chloride.
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Interox(Societe Anonyme)
Patent: US4675131 A1, 1987 ; Title/Abstract Full Text Show Details
The process of claim 8, wherein the acylating agent is selected from the group consisting of acetic anhydride, benzoic anhydride, phthalic anhydride, acetyl chloride, and propionyl chloride.
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Fujisawa Pharmaceutical Co., Ltd.
Patent: US4725600 A1, 1988 ; Title/Abstract Full Text Show Details
32.2:(2)
(2) 6-(3,4-Dimethoxyphenyl)-3-methyl-1-propionyl-1,2,3,4-tetrahydro-4-(2,4,6-trimethylphenylimino)pyrimidine (0.3 g) was obtained by reacting corresponding 1-unsubstituted compound (0.64 g) with propionyl chloride (0.8 ml). mp: 178°-180° C. IR (Nujol): 1690, 1645, 1630 cm-1. NMR (CDCl3, δ): 7.0-6.6 (5H, m), 5.43 (1H, s), 5.04 (2H, s), 3.86 (3H, s), 3.80 (3H, s), 3.15 (3H, s), 2.24 (3H, s), 2.03 (6H, s), 1.92 (2H, q, J=7 Hz), 0.94 (3H, t, J=7 Hz).
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Zoecon Corporation
Patent: US4522647 A1, 1985 ; Title/Abstract Full Text Show Details
7:EXAMPLE 7
EXAMPLE 7 Following the procedure of Example 1 or Example 4, oxalyl chloride and 2-[4-(2-quinolyloxy)phenoxy]propionic acid are reacted together to give the corresponding propionic acid chloride.
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Teijin Limited
Patent: US4838923 A1, 1989 ; Title/Abstract Full Text Show Details
4:EXAMPLE 4 STR25
A solution of the resulting propionyl chloride in 10 parts by volume of ether was added dropwise under ice cooling to a solution of 3.34 parts of diethyl aminophosphonate in 20 parts by volume of ether. Ten minutes later, 1 part by volume of triethylamine was added dropwise. After the addition, the mixture was stirred at room temperature for 3 hours. The reaction mixture was washed with water, a saturated aqueous solution of sodium bicarbonate and water in this order. The organic layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give 2.6 parts of a crude product. The crude product was recrystallized from ethyl acetate/ether to give 1.1 parts of the captioned compound. This compound had a melting point of 134.5° to 135° C., and its IR and NMR spectral data are shown in Table 1.
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SmithKline Corporation
Patent: US4005208 A1, 1977 ; Title/Abstract Full Text Show Details
Similarly, in the above procedure using, in place of ethyl chloroformate, the following: methyl chloroformate butyl chloroformate propionyl chloride
butyryl chloride
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Teijin Limited
Patent: US4009196 A1, 1977 ; Title/Abstract Full Text Show Details
Specific examples of these acid halides and acid anhydrides are shown below. Ii-1-a. acid Halides Acetyl chloride, acetyl bromide, acetyl iodide, acetyl fluoride, propionyl chloride, propionyl bromide, n-butyryl chloride, isobutyryl chloride, n-valeryl chloride, ...
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Sumitomo Chemical Company, Limited
Patent: US4055565 A1, 1977 ; Title/Abstract Full Text Show Details
Examples of an acid halide of the Formula III or IV are as follows: ... Acetyl bromide Acetyl iodide Chloroacetyl chloride Bromoacetyl chloride Propionyl chloride Butyryl chloride Isobutyryl chloride Cyclohexane carbonyl chloride ...
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Mioskowski, Charles; Wagner, Alain; Bensel, Nicolas; Pevere, Virginie; Desmurs, Jean-Roger
Patent: US2003/92946 A1, 2003 ; Title/Abstract Full Text Show Details
Illustrative examples of acylation agents with formula (VIII) which can in particular be cited are: acetyl chloride; acetyl bromide; monochloroacetyl chloride; dichloroacetyl chloride; propanoyl chloride; isobutanoyl chloride; pivaloyl chloride; stearoyl chloride; crotonyl chloride; ...
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Rhodia Chimie
Patent: US6184418 B2, 2001 ; Title/Abstract Full Text Show Details
To give an idea of the acylation agents that match formula (II) we can the following in particular: acetyl chloride, monochloroacetyl chloride, dichloroacetyl chloride, propanoyl chloride, isobutanoyl chloride, pivaloyl chloride, stearoyl chloride, crotonyl chloride, benzoyl chloride, ...
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Rhodia Chimie
Patent: US6194616 B1, 2001 ; Title/Abstract Full Text Show Details
Particular illustrative examples of acylation agents with formula (II) are: acetic anhydride; ... dichloroacetyl anhydride; acetyl chloride; monochloroacetyl chloride; dichloroacetyl chloride; propanoyl chloride; isobutanoyl chloride; pivaloyl chloride; stearoyl chloride;; ...
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UNIVERSITY COLLEGE DUBLIN
Patent: EP1500969 A1, 2005 ; Title/Abstract Full Text Show Details
4:XXVIII: β-(10-phenothiazyl) propionic acid chloride
XXVIII: β-(10-phenothiazyl) propionic acid chloride XXVII (1.0 g) was refluxed in 10 mL of oxazyl chloride for 3 h. Removal of oxazyl chloride under low pressure afforded the crude acid chloride XXVIII which was taken for the next step without further purification. 1H NMR (chloroform-d): δ 3.40-3.45 (t, 2H, J=7.9 Hz); δ 4.27-4.32 (t, 2H, J=7.9 Hz); δ 6.87-7.25 (m, 8H, aromatic)
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UNIVERSITY COLLEGE DUBLIN
Patent: EP1500969 A1, 2005 ; Title/Abstract Full Text Show Details
6:XXI: β-(10-phenoxazyl) propionic acid chloride
XXI: β-(10-phenoxazyl) propionic acid chloride XX (1.0 g) was refluxed in 10mL of oxazyl chloride for 3 h. Removal of oxazyl chloride under low pressure afforded the crude acid chloride XXI which was taken for the next step without further purification. 1H NMR (chloroform-d): δ 3.19-3.28 (t, 2H, J=7.9 Hz); δ 3.90-3.99 (t, 2H, J=7.9 Hz); δ 6.47-6.90 (m, 8H, aromatic) Institute of Pharmacology and Toxicology Academy of Military Medical Sciences P.L.A.
Patent: EP2042494 A1, 2009 ; Location in patent: Page/Page column 46 ; Title/Abstract Full Text Show Details
Li, Song; Guo, Changbin; Jiang, Xiancheng; Xiao, Junhai; Wu, Zhong
Patent: US2009/298832 A1, 2009 ; Location in patent: Page/Page column 32 ; Title/Abstract Full Text Show Details
A
B
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8
A: 5%
Rx-ID: 24012021 Find similar reactions
Alanine, Alexander; Flohr, Alexander; Miller, Aubry Kern; Norcross, Roger David; Riemer, Claus
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Patent: US2002/45615 A1, 2002 ; Title/Abstract Full Text Show Details
N-(4-Methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-propionamide
N-(4-Methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-propionamide Using 4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl-amine and propionyl chloride the title compound was obtained as a light yellow solid (5percent), MS: m/e=322 (M+H+). A
B
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9
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E. I. du Pont de Nemours and Company Patent: US6057336 A1, 2000 ; Title/Abstract Full Text Show Details
[1(R)]-α-[3-amino-3-[4-[(2,6-dimethyl-4-pyridinyl)methoxy]phenyl]-2-oxo-1-pyrrolidinyl]-N-hydroxy-1-(1-oxopropyl)-4-piperidineacetamide bis(trifluoroacetate)
[1(R)]-α-[3-amino-3-[4-[(2,6-dimethyl-4-pyridinyl)methoxy]phenyl]-2-oxo-1-pyrrolidinyl]-N-hydroxy-1-(1-oxopropyl)-4-piperidineacetamide bis(trifluoroacetate) Beginning with the piperidine from (505a) and propionyl chloride, example 527 was prepared in an analogous series of reactions to (49a) and (92d). MS found: (M+H)+ =524. A
B
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10
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Zambon Group S.p.A.
Patent: US5519054 A1, 1996 ; Title/Abstract Full Text Show Details
7:Preparation of S-propionyl-N-acetyl-L-cysteine Isopropyl Ester
EXAMPLE 7 Preparation of S-propionyl-N-acetyl-L-cysteine Isopropyl Ester By working in a similar way to that described in example 2 but by using propionyl chloride instead of isobutyryl chloride, S-propionyl-N-acetyl-L-cysteine isopropyl ester was prepared. [α]D20 =-27.7° (c=1percent, methanol).
m.p. 54°-55° C. 1 H-NMR (200 MHz, DMSO-d6): δ (ppm): 6.27 (broad signal, 1H, NH); 4.98 (m, 1H, COOH); 4.76-4.67 (m, 1H, CH--CH2); 3.41-3.23 (m, 2H, SCH2); 2.54 (q, 2H, JHH =7.5 Hz, SCOCH2); 1.96 (s, 3H, COCH3); 2.45 [d, 6H, JHH =6.2 Hz, CH(CH3)2 ]; 1.13 (T, 3H, CH2 --CH3).
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ZAMBON GROUP S.p.A.
Patent: EP499882 A1, 1992 ; Title/Abstract Full Text Show Details
7:Preparation of S-propionyl-N-acetyl-L-cysteine isopropyl ester
Example 7 Preparation of S-propionyl-N-acetyl-L-cysteine isopropyl ester By working in a similar way to that described in example 2 but by using propionyl chloride instead of isobutyryl chloride, S-propionyl-N-acetyl-L-cysteine isopropyl ester was prepared. [α]20D=-27.7° (c=1percent, methanol)
m.p. 54-55°C 1H-NMR (200 MHz, DMSO-d ): δ (ppm): 6.27 (broad signal, 1H, NH); 4.98 (m, 1H, COOH); 4.76-4.67 (m, 1H, C H -CH ); 3.41-3.23 (m, 2H, SCH ); 2.54 (q, 2H, J =7.5 Hz, SCOCH ); 1.96 (s, 3H, COCH ); 2.45 [d, 6H, J =6.2 Hz, CH(C H ) ]; 1.13 (T, 3H, CH -C H ). 6 2 2 HH 2 3 HH 3 2 2 3 A
B
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11
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A: 57.9%
With phosphorus trichoride
T=40 - 50°C; 4-5h;
Valitova, L. A.; Popova, E. V.; Ibragimov, Sh. N.; Ivanov, B. E.
Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1990 , vol. 39, # 2.2 p. 366 - 370 Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1990 , # 2 p. 428 - 432 Title/Abstract Full Text View citing articles Show Details
A: 46.4% B: 18%
With phosphorus trichoride
T=40 - 50°C; 4-5h;
Valitova, L. A.; Popova, E. V.; Ibragimov, Sh. N.; Ivanov, B. E.
Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1990 , vol. 39, # 2.2 p. 366 - 370 Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1990 , # 2 p. 428 - 432 Title/Abstract Full Text View citing articles Show Details
A
B
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12
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With hydrogenchloride; ozone; formic acid ethyl ester
T=-10 - 0°C;
A
13
Gaeb, Siegmar; Turner, Walter V.; Hellpointer, Eduard; Korte, Friedhelm
Chemische Berichte, 1985 , vol. 118, # 7 p. 2571 - 2578 Title/Abstract Full Text Show Details
B
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Zoecon Corporation
Patent: US4522647 A1, 1985 ; Title/Abstract Full Text Show Details
8:EXAMPLE 8
EXAMPLE 8 Following the procedure of Example 1 or Example 4, oxalyl chloride and 2-[4-(2-quinoxalinyloxy)phenoxy]propionic acid are reacted together to give the corresponding propionic acid chloride. The acid chloride is then reacted with the sodium salt or methylacetoacetate to give methyl 2-acetyl-4-[4-(2-quinoxalinyloxy)phenoxy]-3-oxopentanoate (XIV; X' is hydrogen and X" is hydrogen). A
B
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14
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Zoecon Corporation
Patent: US4522647 A1, 1985 ; Title/Abstract Full Text Show Details
11:EXAMPLE 11
EXAMPLE 11 Following the procedure of Example 8, 2-[4-(6-fluoro-2-quinoxalinyloxy)phenoxy]propionic acid is reacted with oxalyl chloride to give the corresponding propionic acid chloride, which is then reacted with the sodium salt of methylacetoacetate to give methyl 2-acetyl-4-[4-(6-fluoro-2-quinoxalinyloxy)phenoxy]-3-oxopentanoate (XIV; X' is fluoro and X" is hydrogen). A
B
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15
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Rx-ID: 1946472 Find similar reactions
B: 41%
in 1,2-dichloro-ethane
12 h; Heatingcourse is discussed; further trimethylsilyl carboxylates, aldehydes and ketones; Mechanism;
Hofmann, Karin; Simchen, Gerhard
Liebigs Annalen der Chemie, 1984 , # 1 p. 39 - 47 Title/Abstract Full Text Show Details
B: 41%
in 1,2-dichloro-ethane
12 h; Heating;
Hofmann, Karin; Simchen, Gerhard
Liebigs Annalen der Chemie, 1984 , # 1 p. 39 - 47 Title/Abstract Full Text Show Details
A
B
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16
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Rx-ID: 25002741 Find similar reactions
Byk Gulden Lomberg Chemische Fabrik GmbH
Patent: US4243678 A1, 1981 ; Title/Abstract Full Text Show Details
84:Sodium 4-[N-(6-methoxy-1,2,3,4-tetrahydro-1-naphthyl)propionamido]butyrate
EXAMPLE 84 Sodium 4-[N-(6-methoxy-1,2,3,4-tetrahydro-1-naphthyl)propionamido]butyrate R1 =--CH2 --CH3, R=6-methoxy-1,2,3,4-tetrahydro-1-naphthyl, n=3
Following the process of Example 82 and replacing 1-amino-1,2,3,4-tetrahydro]naphthalene and acetyl chloride by 6-methoxy-1-amino-1,2,3,4-tetrahydronaphthalene and propionyl chloride, 4-[N-(6-methoxy-1,2,3,4-tetrahydro-1-naphthyl)propionamido]butyric acid is obtained as a viscous oil which does not crystallize even after several weeks. A
B
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17
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Gulf Research and Development Company
Patent: US3932660 A1, 1976 ; Title/Abstract Full Text Show Details
5:EXAMPLE 5
The reaction mixture was then distilled to give 10.5 g of 2-methyldithio-2-methylpropionyl chloride, b.p. 100°-122°C. at 55 mm of Hg. The 10.5-g sample of propionyl chloride prepared above was added dropwise over a 10-minute period to 12 g 2,4,6-trichlorophenylhydrazine and 6 g triethylamine in 250 ml glyme. After stirring for 10 minutes, 200 ml ice water and 10 ml concentrated hydrochloric acid were added. On stirring in an ice bath, a solid separated. The solid was filtered, washed with water, dried and recrystallized from hexane to give the hydrazide product (Formula V, where Ar is 2,4,6-trichlorophenyl, R1, R2 and R3 are methyl and n is 2) as a beige solid, m.p. 86-88°C.
By a procedure similar to that of Example 4, the hydrazide product prepared above was chlorinated with phosphorus pentachloride to give the hydrazone disulfide product of the formula SPC5 Elemental analysis for C11 H12 Cl4 N2 S2 showed: percentS, calc. 17.0, found 17.1; percentCl, calc. 37.5, found 40.9. A
B
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18
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Boehringer Ingelheim GmbH
Patent: US3933832 A1, 1976 ; Title/Abstract Full Text Show Details
7:EXAMPLE 7
EXAMPLE 7 Using a procedure analogous to that described in Example 1, 24percent of theory of 4-[N-(α-pyridyl)-N-(propionyl-amino]-1-(γ-phenyl-n-propyl)-piperidine and its hydrochloride, m.p. 119°-124°C, of the formula SPC13 was obtained from 4-[N-(α-pyridyl)-amino]-1-(γ-phenyl-n-propyl)-piperidine and propionyl chloride.
19
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Rx-ID: 6219026 Find similar reactions
T=-15 - -5°C; unter Lichtausschluss;
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Boehme; Schmitz
Chemische Berichte, 1955 , vol. 88, p. 357,361 Full Text View citing articles Show Details
20
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Rx-ID: 5817931 Find similar reactions
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T=20°C;
Cade; Gerrard
Journal of the Chemical Society, 1954 , p. 2030,2033 Full Text View citing articles Show Details
21
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Rx-ID: 615158 Find similar reactions
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Brown
Journal of the American Chemical Society, 1938 , vol. 60, p. 1326 Full Text View citing articles Show Details
Roberts et al.
Journal of the American Chemical Society, 1950 , vol. 72, p. 4237,4242 Org.Synth.Isotopes, 1958 , p. 378 Full Text View citing articles Show Details
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