1-Naphthoyl chloride [C11H7ClO] by Asch

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12 reactions in Reaxys

2018-02-11 11h:14m:13s (EST)

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Rx-ID: 281899 View in Reaxys 1/12 Yield 100 %

Conditions & References General Procedure for Synthesis of Carboxamide Derivatives 1–8c General procedure: Method A: Naphthalene-1-carboxylic acid (5.8 mmol) was dissolved in dry hot toluene (40 mL) and thionyl chloride (8.0 mmol) was added. After 2 h of refluxing, solvent and excessive thionyl chloride were evaporated under reduced pressure giving napthalene-1-carbonyl chloride as colourless liquid in quantitative yield. The product forms colourless needles after cooling. Mp. 18–19 °C (26 °C [54]). Naphthalene-1-carbonyl chloride (5.8 mmol), triethylamine (8.7 mmol) and corresponding substituted aniline (5.8 mmol) were dissolved in dry dichloromethane (30 mL) and the mixture was stirred for 12 h at ambient temperature. The solvent was evaporated under reduced pressure, the solid residue washed with 10percent HCl, and the crude product was recrystallized from propan-2-ol with addition of active carbon. With thionyl chloride in toluene, Time= 2h, Reflux Gonec, Tomas; Kos, Jiri; Nevin, Eoghan; Govender, Rodney; Pesko, Matus; Tengler, Jan; Kushkevych, Ivan; Stastna, Vendula; Oravec, Michal; Kollar, Peter; O'mahony, Jim; Kralova, Katarina; Coffey, Aidan; Jampilek, Josef; Molecules; vol. 19; nb. 7; (2014); p. 10386 - 10409 View in Reaxys

98 %

B :Napthalene-1-carbonyl chloride.; 1-Napthoic acid (1.0 g, 5.81 mmol) dissolved in thionyl chloride (5 ml) and refluxed for 2 hours. Thionyl chloride was removed under reduced pressure, co-evaporated with benzene (2 x 5 mL) to obtain napthalene-1 -carbonyl chloride (1.01 g, 98percent) as a liquid. Since this acid chloride was not very stable, it was used m the next step without further purification and characterization. With thionyl chloride, Time= 2h, Heating / reflux Patent; CHATTOPADHYAYA, Jyoti; UPADHAYAYA, Ram Shankar; WO2009/91324; (2009); (A1) English View in Reaxys

96 %

With thionyl chloride, N,N-dimethyl-formamide in benzene, Time= 2h Yu, Su; Rabalakos, Constantinos; Mitchell, William D.; Wulff, William D.; Organic Letters; vol. 7; nb. 3; (2005); p. 367 - 369 View in Reaxys With phosphorus pentachloride v. Braun; Chemische Berichte; vol. 38; (1905); p. 180 View in Reaxys Hofmann,A.W.; Chemische Berichte; vol. 1; (1868); p. 42 View in Reaxys With thionyl chloride Stolle; Journal fuer Praktische Chemie (Leipzig); vol. <2> 74; (1906); p. 19 View in Reaxys With thionyl chloride, N,N-dimethyl-formamide in benzene, Time= 2h Harvey, Ronald G.; Cortez, Cecilia; Jacobs, Stephen A.; Journal of Organic Chemistry; vol. 47; nb. 11; (1982); p. 2120 - 2125 View in Reaxys With thionyl chloride Barton, Derek H.R.; Lacher, Brigitte; Zard, Samir Z.; Tetrahedron; vol. 43; nb. 19; (1987); p. 4321 - 4328 View in Reaxys With thionyl chloride in dichloromethane, 0 deg C, then reflux 6 h Meyers, A.I.; Lutomski, Kathryn A.; Laucher, Dominique; Tetrahedron; vol. 44; nb. 11; (1988); p. 3107 - 3118

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View in Reaxys With oxalyl dichloride, N,N-dimethyl-formamide in benzene, Ambient temperature DeRuiter, Jack; Swearingen, Blake E.; Wandrekar, Vinay; Mayfield, Charles A.; Journal of Medicinal Chemistry; vol. 32; nb. 5; (1989); p. 1033 - 1038 View in Reaxys With thionyl chloride, N,N-dimethyl-formamide, Ambient temperature Eissenstat, Michael A.; Bell, Malcolm R.; D'Ambra, Thomas E.; Alexander, E. John; Daum, Sol J.; et al.; Journal of Medicinal Chemistry; vol. 38; nb. 16; (1995); p. 3094 - 3105 View in Reaxys With oxalyl dichloride, N,N-dimethyl-formamide in dichloromethane, Time= 2h, Ambient temperature Shimano, Masanao; Meyers, A. I.; Journal of Organic Chemistry; vol. 60; nb. 23; (1995); p. 7445 - 7455 View in Reaxys With thionyl chloride in dichloromethane, Time= 2.5h Bowles, Peter; Clayden, Jonathan; Helliwell, Madeleine; McCarthy, Catherine; Tomkinson, Matthew; Westlund, Neil; Journal of the Chemical Society - Perkin Transactions 1; nb. 17; (1997); p. 2607 - 2616 View in Reaxys With oxalyl dichloride, N,N-dimethyl-formamide in dichloromethane, Time= 6h, Chlorination Vedejs; Kruger; Suna; Journal of Organic Chemistry; vol. 64; nb. 21; (1999); p. 7863 - 7870 View in Reaxys With thionyl chloride in chloroform, Time= 4h, Heating, Substitution Diouf, Ousmane; Depreux, Patrick; Chavatte, Philippe; Poupaert, Jacques Henri; European Journal of Medicinal Chemistry; vol. 35; nb. 7-8; (2000); p. 699 - 706 View in Reaxys With thionyl chloride in benzene, Time= 3h, Heating Sriraghavan, Kamaraj; Ramakrishnan, Vayalakkavoor T.; Tetrahedron; vol. 59; nb. 10; (2003); p. 1791 - 1796 View in Reaxys With thionyl chloride in 1,2-dichloro-ethane, Time= 1h, T= 50 °C Mai, Antonello; Massa, Silvio; Cerbara, Ilaria; Valente, Sergio; Ragno, Rino; Bottoni, Patrizia; Scatena, Roberto; Loidl, Peter; Brosch, Gerald; Journal of Medicinal Chemistry; vol. 47; nb. 5; (2004); p. 1098 - 1109 View in Reaxys With thionyl chloride, Time= 2h, T= 70 °C Willis, Peter G.; Pavlova, Olga A.; Chefer, Svetlana I.; Vaupel, D. Bruce; Mukhin, Alexey G.; Horti, Andrew G.; Journal of Medicinal Chemistry; vol. 48; nb. 18; (2005); p. 5813 - 5822 View in Reaxys With thionyl chloride, triethylamine Leopoldo, Marcello; Lacivita, Enza; Colabufo, Nicola A.; Contino, Marialessandra; Berardi, Francesco; Perrone, Roberto; Journal of Medicinal Chemistry; vol. 48; nb. 25; (2005); p. 7919 - 7922 View in Reaxys With thionyl chloride, Time= 1h, T= 80 °C Rudrawar, Santosh; Kondaskar, Atul; Chakraborti, Asit K.; Synthesis; nb. 15; (2005); p. 2521 - 2526; Art.No: Z05105SS View in Reaxys With oxalyl dichloride in dichloromethane, Time= 2h

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Chen, Xiao; Li, Jiao-Jie; Hao, Xue-Shi; Goodhue, Charles E.; Yu, Jin-Quan; Journal of the American Chemical Society; vol. 128; nb. 1; (2006); p. 78 - 79 View in Reaxys With thionyl chloride, Time= 2h, Heating, Substitution Brunner, Henri; Schmidt, Peter; European Journal of Organic Chemistry; nb. 11; (2000); p. 2119 - 2133 View in Reaxys With thionyl chloride, N,N-dimethyl-formamide KrennHrubec, Keris; Marshall, Brett L.; Hedglin, Mark; Verdin, Eric; Ulrich, Scott M.; Bioorganic and Medicinal Chemistry Letters; vol. 17; nb. 10; (2007); p. 2874 - 2878 View in Reaxys 79 : EXAMPLE 79 EXAMPLE 79 A mixture of 1.03 g of 1-naphthoic acid and 4.86 g of thionyl chloride was stirred at 50° C. for 2 hours. An excess of thionyl chloride was removed under reduced pressure to give 1-naphthoyl chloride. With thionyl chloride Patent; Kaken Pharmaceutical Co., Ltd.; US5021458; (1991); (A1) English View in Reaxys 14 :To a stirred suspension of 1-napthoic acid (8.61 g, 0.050 mol) in CH2Cl2 (150 ml) was added SOCl2 (23.79 g,0.20 mol) and the mixture was heated under reflux for 4 h. The mixture was evaporated in vacuo to leave the acid chloride as a solid material. This was dissolved in CH2Cl2 (150 ml) and added dropwise to a stirred solution of 4-amino-lbenzylpiperidine (9.51 g, 0.050 mol) and NEt3 (5.06 g, 0.05 mol) in CH2Cl2 (100ml) at O0C. The mixture was stirred at room temperature for 24 h and washed with H2O (3 x 75 ml) The organic layer was dried over Na2SO4 and evaporated in vacuo to a solid material. This was recrystallized from ethanol/water (40/60) EPO <DP n="29"/>to leave the product as a white solid (7.8 g, 45.3percent).1H-NMR (300 MHz, CDCl3) : δ 8.32-8.27 (m, 1 H), 7.90 (t, 2 H), 7.57-7.30 (m, 9 H), 6.17 (d, 2 H), 4.17-4.06 (m, 1 H), 3.55 (s, 2H), 2.88 (d, 2 H) , 2.27-2.05 (m, 4 H) , 1.69-1.50 (m, 2 H) With thionyl chloride in dichloromethane, Time= 4h, Heating / reflux Patent; BIO-MEDISINSK INNOVASJON AS; COCKBAIN, Julian; WO2007/7072; (2007); (A1) English View in Reaxys With thionyl chloride, Time= 1h, T= 80 °C Kumar, Dinesh; Rudrawar, Santosh; Chakraborti, Asit K.; Australian Journal of Chemistry; vol. 61; nb. 11; (2008); p. 881 - 887 View in Reaxys With trichloroacetamide, triphenylphosphine in dichloromethane, Time= 1h, Reflux Chantarasriwong, Oraphin; Jang, Doo Ok; Chavasiri, Warinthorn; Synthetic Communications; vol. 38; nb. 16; (2008); p. 2845 - 2856 View in Reaxys 33.b : b) naphthalene-1-carboxylic acid 1-methyl-4-phenyl-piperidin-4-ylmethyl ester b) naphthalene-1-carboxylic acid 1-methyl-4-phenyl-piperidin-4-ylmethyl ester. To a suspension containing 1-naphthoic acid (445 mg, 2.58 mmol) and CH2Cl2 (25 mL) was added oxalyl chloride (0.293 mL, 3.35 mmol) and then DMF (2 drops). Reaction was stirred at RT for 1 h. Solvent was removed in vacuo. This material was dissolved in 1,2- dichloroethane (10 mL) and added to a solution containing 1-N-methyl-4-hydroxymethyl-4- phenylpiperidine, (0.53g, 2.58 mmol, Example 31) triethylamine (392 mg, 3.87 mmol) and 1,2-dichloroethane (10 mL). Reaction was stirred at RT for 20 min, and then heated to 60 °C overnight. Reaction was cooled and solvent removed in vacuo. Residue was purified by chromatography (4percent MeOH/95.6percent CH2Cl2/0.4percent NH4OH) and concentrated to give the title compound (74percent yield, 683 mg) as a tan solid. MS m/z 360 (M+H). With oxalyl dichloride, N,N-dimethyl-formamide in dichloromethane, Time= 1h, T= 20 °C Patent; ASTRAZENECA AB; WO2004/22539; (2004); (A1) English

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View in Reaxys 5 :Example 5 Preparation of intermediate N-(1-benzylpiperidin-4-yl)napth-1-yl carboxamide A stirred suspension of 1-napthoic acid (8.61 g, 0.050 mol) in CH2CI2 (150 ml) was added SOC12 (23.79 g, 0.20 mol) and the mixture heated under reflux for 4 h. The mixture was evaporated in vacuo to leave the acid chloride as a solid material. This was dissolved in CH2Cl2 (150 ml) and added dropwise to a stirred solution of piperidine (9.51 g, 0.050 mol) and NEt3 (5.06 g, 0.05 mol) in CHzCIz (lOOml) at 0 °C. The mixture was stirred to room temperature for 24 h and washed with H20 (3 x 75 ml) The organic layer was dried over Na2SO4 and evaporated in vacuo to a solid material. This was recrystallized from ethanol/water (40/60) to leave the product as a white solid (7.8 g, 45.3 percent). 1H-NMR (300 MHz, CDCl3) : 5 8.32-8. 27 (m, 1 H), 7.90 (t, 2 H), 7.57-7. 30 (m, 9 H), 6.17 (d, 2 H), 4.17-4. 06 (m, 1 H), 3.55 (s, 2H), 2.88 (d, 2 H), 2.27-2. 05 (m, 4 H), 1.69-1. 50 (m, 2 H) With thionyl chloride in dichloromethane, Time= 4h, Heating / reflux Patent; BIO-MEDISINSK INNOVASJON AS; WO2005/61483; (2005); (A2) English View in Reaxys With oxalyl dichloride, N,N-dimethyl-formamide in toluene, Time= 6h, T= 20 °C Chang, Yu-Hsun; Hsu, Mei-Hua; Wang, Sheng-Hung; Huang, Li-Jiau; Qian, Keduo; Morris-Natschke, Susan L.; Hamel, Ernest; Kuo, Sheng-Chu; Lee, Kuo-Hsiung; Journal of Medicinal Chemistry; vol. 52; nb. 15; (2009); p. 4883 - 4891 View in Reaxys 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; vol. 17; nb. 22; (2009); p. 7690 - 7697 View in Reaxys With oxalyl dichloride, N,N-dimethyl-formamide in dichloromethane, T= 20 °C Laval, Stephane; Dayoub, Wissam; Favre-Reguillon, Alain; Demonchaux, Patrice; Mignani, Gerard; Lemaire, Marc; Tetrahedron Letters; vol. 51; nb. 16; (2010); p. 2092 - 2094 View in Reaxys With thionyl chloride, N,N-dimethyl-formamide, Time= 3h, T= 65 °C , Reflux Chen, Yu; Zhao, Zhi Gang; Liu, Xing Li; Shi, Zhi Chuan; Journal of Chemical Research; nb. 7; (2010); p. 416 420 View in Reaxys With thionyl chloride Khan, Khalid Mohammed; Ahmed, Sumbul; Hussain, Sajjad; Ambreen, Nida; Perveen, Shahnaz; Choudhary, M. Iqbal; Letters in Drug Design and Discovery; vol. 7; nb. 4; (2010); p. 265 - 268 View in Reaxys With thionyl chloride in benzene, Time= 1h, Reflux Rajak, Harish; Behera, Chinmay K.; Pawar, Rajesh S.; Singour, Pradeep K.; Kharya, Murli Dhar; Chinese Chemical Letters; vol. 21; nb. 10; (2010); p. 1149 - 1152 View in Reaxys With thionyl chloride, Time= 2h, Reflux Kuang, Gui-Chao; Teng, Ming-Jun; Jia, Xin-Ru; Chen, Er-Qiang; Wei, Yen; Chemistry - An Asian Journal; vol. 6; nb. 5; (2011); p. 1163 - 1170 View in Reaxys With oxalyl dichloride, N,N-dimethyl-formamide in dichloromethane, Time= 5h, T= 0 - 20 °C , Inert atmosphere Ano, Yusuke; Tobisu, Mamoru; Chatani, Naoto; Organic Letters; vol. 14; nb. 1; (2012); p. 354 - 357 View in Reaxys

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10 :Example 101-Naphthoic acid ethylamide Thionyl chloride (2.5 mL, 34.8 mmol) was added in a dropwise fashion at ambient temperature with stirring to 1-naphthoic acid (500 mg, 2.9 mmol) under an atmosphere of N2. The reaction mixture was then heated to 80° C. for 2 hours before the excess thionyl chloride was removed under reduced pressure. The residue was dissolved in THF (25 mL) and cooled on an ice-bath before ethylamine in H2O (70percent, 0.26 mL, 3.19 mmol) was added. The reaction mixture was stirred at ambient temperature overnight before it was poured onto a saturated aqueous solution of NaHCO3 (60 mL). The mixture was then extracted with CH2Cl2 (3*60 mL) and the combined organic phases dried (MgSO4), filtered, and concentrated under reduced pressure. The remaining material was purified by column chromatography (silica, AcOEt/petrolether 2:1) to give the 1-Naphthoic acid ethylamide (103 mg, 18percent).1H-NMR (CDCl3, 400 MHz) δH 8.29 (d, 1H, J 8.4 Hz), 7.90-7.84 (m, 2H), 7.57-7.49 (m, 3H), 7.43 (t, 1H, J 7.2 Hz), 6.03 (b s, 1H), 3.60-3.53 (m, 2H), 1.28 (t, 3H, J 7.2 Hz). 13C-NMR (CDCl3, 100 MHz) δC 169.6, 134.9, 133.8, 130.5, 130.3, 128.4, 127.2, 126.5, 125.5, 124.9, 124.8, 35.1, 15.1. With thionyl chloride, Time= 2h, T= 20 - 80 °C , Inert atmosphere Patent; REGION MIDT JYLLAND; AARHUS UNIVERSITET; US2012/95048; (2012); (A1) English View in Reaxys With thionyl chloride, Reflux Zhang, Jian; Yang, Nianfa; Yang, Liwen; Molecules; vol. 17; nb. 6; (2012); p. 6415 - 6423 View in Reaxys With bis(trichloromethyl) carbonate, N,N-dimethyl-formamide in dichloromethane, Time= 3h, T= 40 °C Lin, Qi; Zhang, You-Ming; Li, Man-Lin; Wei, Tai-Bao; Synthetic Communications; vol. 42; nb. 22; (2012); p. 3251 3260 View in Reaxys With thionyl chloride, Time= 4h, Reflux Mao, Wu Tao; Zhao, Hui; Fan, Zhi Jin; Ji, Xiao Tian; Hua, Xue Wen; Kalinina, Tatiana; Yury, Yu. Morzherin; Vasiliy, A. Bakulev; Chinese Chemical Letters; vol. 23; nb. 11; (2012); p. 1233 - 1236,4 View in Reaxys With oxalyl dichloride in dichloromethane, N,N-dimethyl-formamide, Time= 5h, T= 0 - 20 °C , Inert atmosphere Aihara, Yoshinori; Chatani, Naoto; Journal of the American Chemical Society; vol. 135; nb. 14; (2013); p. 5308 5311 View in Reaxys With thionyl chloride, Time= 4h, Reflux Bonsignore, Martina; Benaglia, Maurizio; Raimondi, Laura; Orlandi, Manuel; Celentano, Giuseppe; Beilstein Journal of Organic Chemistry; vol. 9; (2013); p. 633 - 640 View in Reaxys With thionyl chloride, T= 60 - 80 °C Gao, Xi-Ai; Wang, Xian-Xue; Yan, Hao; Li, Jian; Yan, Ru-Long; Huang, Guo-Sheng; Journal of the Indian Chemical Society; vol. 90; nb. 3; (2013); p. 381 - 385 View in Reaxys With oxalyl dichloride in hexane, N,N-dimethyl-formamide, Time= 1h, T= 20 °C Lourido, Sebastian; Zhang, Chao; Lopez, Michael S.; Tang, Keliang; Barks, Jennifer; Wang, Qiuling; Wildman, Scott A.; Shokat, Kevan M.; Sibley, L. David; Journal of Medicinal Chemistry; vol. 56; nb. 7; (2013); p. 3068 - 3077 View in Reaxys With ((1,3,5-triazine-2,4,6-triyl)tris(oxy))tris(triphenylphosphonium) chloride, Time= 0.5h, T= 140 - 150 °C Sugimoto, Osamu; Harada, Yukihiro; Tanji, Ken-Ichi; Heterocycles; vol. 86; nb. 2; (2012); p. 1583 - 1590 View in Reaxys With thionyl chloride, Microwave irradiation

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Peng, Yongle; Liu, Xingli; Gu, Jian; Zhao, Zhigang; Journal of Chemical Research; vol. 37; nb. 7; (2013); p. 413 416 View in Reaxys With thionyl chloride in toluene, Time= 4h, Reflux Micksch, Maik; Tenne, Mario; Strassner, Thomas; European Journal of Organic Chemistry; nb. 27; (2013); p. 6137 - 6145 View in Reaxys With thionyl chloride, N,N-dimethyl-formamide in toluene, Time= 3h, T= 80 °C Misal Castro, Luis C.; Chatani, Naoto; Chemistry - A European Journal; vol. 20; nb. 16; (2014); p. 4548 - 4553 View in Reaxys With oxalyl dichloride, N,N-dimethyl-formamide in dichloromethane, Time= 5h, T= 0 - 20 °C , Inert atmosphere, Schlenk technique Al Mamari, Hamad H.; Diers, Emelyne; Ackermann, Lutz; Chemistry - A European Journal; vol. 20; nb. 31; (2014); p. 9739 - 9743 View in Reaxys With thionyl chloride Hussain, Zaib; Khan, Zulfiqar Ali; Naqvi, Syed Ali Raza; Shahzad, Sohail Anjum; Yar, Muhammad; Hussain, Abdullah Ijaz; Chatha, Shahzad Ali Shahid; Mahmood, Nasir; Khan, Khalid Mohammed; Journal of the Chemical Society of Pakistan; vol. 35; nb. 2; (2013); p. 449 - 455 View in Reaxys With thionyl chloride in dichloromethane, N,N-dimethyl-formamide, Time= 5h, T= 60 °C , Inert atmosphere Katayev, Dmitry; Pfister, Kai F.; Wendling, Timo; Goossen, Lukas J.; Chemistry - A European Journal; vol. 20; nb. 32; (2014); p. 9902 - 9905 View in Reaxys With oxalyl dichloride in dichloromethane, N,N-dimethyl-formamide Shang, Ming; Wang, Hong-Li; Sun, Shang-Zheng; Dai, Hui-Xiong; Yu, Jin-Quan; Journal of the American Chemical Society; vol. 136; nb. 33; (2014); p. 11590 - 11593 View in Reaxys With oxalyl dichloride in dichloromethane, N,N-dimethyl-formamide, Time= 3h, T= 0 - 20 °C , Inert atmosphere Aihara, Yoshinori; Tobisu, Mamoru; Fukumoto, Yoshiya; Chatani, Naoto; Journal of the American Chemical Society; vol. 136; nb. 44; (2014); p. 15509 - 15512 View in Reaxys With thionyl chloride, N,N-dimethyl-formamide in dichloromethane, T= 0 °C , Inert atmosphere Zhang, Shang-Shi; Wu, Jia-Qiang; Lao, Ye-Xing; Liu, Xu-Ge; Liu, Yao; Lv, Wen-Xin; Tan, Dong-Hang; Zeng, Yao-Fu; Wang, Honggen; Organic Letters; vol. 16; nb. 24; (2014); p. 6412 - 6415 View in Reaxys With oxalyl dichloride, N,N-dimethyl-formamide in chloroform, T= 20 °C , Inert atmosphere Ko, Eun Jung; Williams, Craig M.; Savage, G. Paul; Tsanaktsidis, John; Organic Letters; vol. 13; nb. 8; (2011); p. 1944 - 1947 View in Reaxys With thionyl chloride, Time= 2h, Reflux Liu, Yue-Jin; Liu, Yan-Hua; Yin, Xue-Song; Gu, Wen-Jia; Shi, Bing-Feng; Chemistry--A European Journal; vol. 21; nb. 1; (2015); p. 205 - 209 View in Reaxys With oxalyl dichloride, N,N-dimethyl-formamide in dichloromethane, T= 20 °C , Inert atmosphere

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Roman, Daniela Sustac; Poiret, Valentin; Pelletier, Guillaume; Charette, Andr B.; European Journal of Organic Chemistry; vol. 2015; nb. 1; (2015); p. 67 - 71 View in Reaxys With oxalyl dichloride, N,N-dimethyl-formamide in dichloromethane Wang, Hong-Li; Shang, Ming; Sun, Shang-Zheng; Zhou, Zeng-Le; Laforteza, Brian N.; Dai, Hui-Xiong; Yu, JinQuan; Organic Letters; vol. 17; nb. 5; (2015); p. 1228 - 1231 View in Reaxys With oxalyl dichloride, N,N-dimethyl-formamide in dichloromethane, Time= 5h, T= 0 - 20 °C , Inert atmosphere Ye, Xiaohan; Petersen, Jeffrey L.; Shi, Xiaodong; Chemical Communications; vol. 51; nb. 37; (2015); p. 7863 7866 View in Reaxys With thionyl chloride, Time= 3h, T= 85 °C , Inert atmosphere Barsu, Nagaraju; Kalsi, Deepti; Sundararaju, Basker; Chemistry - A European Journal; vol. 21; nb. 26; (2015); p. 9364 - 9368 View in Reaxys 5.1.1. N-(3-Bromopropyl)-3,5-dichlorobenzamide (10a) Compound 9a (191 mg, 1 mmol) was refluxed in excess of thionylchloride (3 mL) overnight. Excess of thionyl chloride was evaporatedand the residue was dissolved in CH2Cl2, 3-bromopropylamine hydrobromide (328 mg, 1.5 mmol was addedfollowed by triethylamine (TEA; 0.42 mL, 3 mmol). The reactionmixture was stirred at room temperature. After the reaction wascompleted, the reaction mixture was diluted with CH2Cl2 andsequentially washed with water, 1 N HCl and saturated NaHCO3.The organic layer was dried over MgSO4, filtered and concentrated.The obtained product was purified by column chromatographywith n-hexane/ethyl acetate (EtOAc) = 4:1 to obtain 10a, (236 mg, 76percent) as white solid. With thionyl chloride, Reflux Paudel, Suresh; Cao, Yongkai; Guo, Shuohan; An, Byeongkwan; Kim, Kyeong-Man; Cheon, Seung Hoon; Bioorganic and Medicinal Chemistry; vol. 23; nb. 19; (2015); p. 6418 - 6426; Art.No: 12526 View in Reaxys With thionyl chloride in dichloromethane, Time= 4h, Reflux, Inert atmosphere, Schlenk technique Dai, Huimin; Yu, Chao; Lu, Changsheng; Yan, Hong; European Journal of Organic Chemistry; vol. 2016; nb. 7; (2016); p. 1255 - 1259 View in Reaxys With oxalyl dichloride, N,N-dimethyl-formamide in dichloromethane, T= 0 °C , Inert atmosphere, Schlenk technique Gandeepan, Parthasarathy; Rajamalli, Pachaiyappan; Cheng, Chien-Hong; Angewandte Chemie - International Edition; vol. 55; nb. 13; (2016); p. 4308 - 4311; Angew. Chem.; vol. 128; (2016); p. 4380 - 4383,4 View in Reaxys With thionyl chloride, Time= 0.5h, T= 85 °C , Reflux Wu, Youzhi; Sun, Peng; Zhang, Kaifan; Yang, Tie; Yao, Hequan; Lin, Aijun; Journal of Organic Chemistry; vol. 81; nb. 5; (2016); p. 2166 - 2173 View in Reaxys With thionyl chloride Yang, Zhi-Wei; Zhang, Qi; Jiang, Yuan-Ye; Li, Lei; Xiao, Bin; Fu, Yao; Chemical Communications; vol. 52; nb. 40; (2016); p. 6709 - 6711 View in Reaxys With thionyl chloride, Time= 2h, Reflux Chen, Fa-Jie; Liao, Gang; Li, Xin; Wu, Jun; Shi, Bing-Feng; Organic Letters; vol. 16; nb. 21; (2014); p. 5644 5647 View in Reaxys

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Srimontree, Watchara; Chatupheeraphat, Adisak; Liao, Hsuan-Hung; Rueping, Magnus; Organic Letters; vol. 19; nb. 12; (2017); p. 3091 - 3094 View in Reaxys With oxalyl dichloride in dichloromethane, N,N-dimethyl-formamide, Time= 2h, T= 20 °C Zhou, Xiaorong; Peng, Zhixing; Zhao, Hongyang; Zhang, Zhiyin; Lu, Ping; Wang, Yanguang; Chemical Communications; vol. 52; nb. 70; (2016); p. 10676 - 10679 View in Reaxys With oxalyl dichloride, N,N-dimethyl-formamide in dichloromethane, Time= 1h, T= 20 °C , Inert atmosphere, Sealed tube McClure, Jesse J.; Zhang, Cheng; Inks, Elizabeth S.; Peterson, Yuri K.; Li, Jiaying; James Chou; Journal of Medicinal Chemistry; vol. 59; nb. 21; (2016); p. 9942 - 9959 View in Reaxys General Procedures for Preparations of Aryl-2-oxazolines General procedure: Aryl acid (10 mmol) was dissolved in 20 mL of dried methylene chloride and cooled to 0 °C; 5 drops of DMF was added to the suspension. Oxalyl chloride (12 mmol) was added drop-wise to the reaction mixture. The reaction was warmed to room temperature and stirred for 3 h. The solvent was removed in vacuo and the residue was dried for 1 h on high vacuum. The residue was dissolved in 15 mL of methylene chloride and added drop wise to a suspension of 2-amino-2-methyl-1-propanol (1.39 g, 12 mmol), triethylamine (2.02 g, 20 mmol) in 35 mL of methylene chloride at 0 oC. The reaction stirred for 3 hand was warmed to rt. The reaction was diluted with methylene chloride and washed once with dilute HCl and washed twice with brine. The organic layer was dried, (MgSO4) filtered, and concentrated in vacuo to give the crude amide intermediate. The crude amide intermediate (2.07 g 10 mmol) was dissolved in 50 mL of DCM and triethylamine(1.21 g, 12 mmol) was added. The reaction was stirred for 30 min at 0 oC. Mesyl chloride (1.37 g, 12 mmol) was added drop wise and the reaction warmed to room temperature and stirred for 3 h. The reaction was diluted with DCM and washed twice with dilute HCl and twice with brine. The organic layer was dried,(MgSO4), filtered, and concentrated in vacuo to give the crude mesylate intermediate. The crude mesylate product was purified via flash chromatography in a gradient of hexane ethyl acetate respectively. The purified product was then diluted in 20 mL of ethanol and sodium hydroxide (480 mg, 9.3 mmol) was added and the reaction was stirred for 30 min. The reaction mixture was diluted with ethyl acetate and washed 3 times with brine. The organic layer was dried over MgSO4 filtered and concentrated in vacuo to afford the product after flash chromatography. With oxalyl dichloride, N,N-dimethyl-formamide in dichloromethane, Time= 3h, T= 20 °C , Inert atmosphere Gutierrez, David A.; Lee, Wan-Chen Cindy; Shen, Yuning; Li, Jie Jack; Tetrahedron Letters; vol. 57; nb. 48; (2016); p. 5372 - 5376 View in Reaxys With oxalyl dichloride in dichloromethane, N,N-dimethyl-formamide, Time= 12h, T= 0 - 20 °C Zhou, Zhi; Liu, Guixia; Lu, Xiyan; Organic Letters; vol. 18; nb. 21; (2016); p. 5668 - 5671 View in Reaxys With oxalyl dichloride, N,N-dimethyl-formamide in dichloromethane, Time= 4h, T= 0 - 20 °C , Inert atmosphere Chen, Zenghua; Hu, Le'an; Zeng, Fanyun; Zhu, Ranran; Zheng, Shasha; Yu, Qingzhen; Huang, Jianhui; Chemical Communications; vol. 53; nb. 30; (2017); p. 4258 - 4261 View in Reaxys With thionyl chloride, Time= 2h, Reflux Bera, Sourav Sekhar; Debbarma, Suvankar; Ghosh, Avick Kumar; Chand, Santanu; Maji, Modhu Sudan; Journal of Organic Chemistry; vol. 82; nb. 1; (2017); p. 420 - 430 View in Reaxys With oxalyl dichloride in dichloromethane, N,N-dimethyl-formamide, Time= 5h, T= 0 - 20 °C Liu, Shuang-Liang; Li, Xue-Hong; Shi, Tan-Hao; Yang, Guang-Chao; Wang, Hai-Li; Gong, Jun-Fang; Song, Mao-Ping; European Journal of Organic Chemistry; vol. 2017; nb. 16; (2017); p. 2280 - 2289 View in Reaxys With oxalyl dichloride in dichloromethane, N,N-dimethyl-formamide, Time= 2h, Inert atmosphere

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Lévesque, Éric; Bechara, William S.; Constantineau-Forget, Léa; Pelletier, Guillaume; Rachel, Natalie M.; Pelletier, Joelle N.; Charette, André B.; Journal of Organic Chemistry; vol. 82; nb. 10; (2017); p. 5046 - 5067 View in Reaxys With thionyl chloride in toluene, Time= 5h, Reflux Sevaille, Laurent; Gavara, Laurent; Bebrone, Carine; De Luca, Filomena; Nauton, Lionel; Achard, Maud; Mercuri, Paola; Tanfoni, Silvia; Borgianni, Luisa; Guyon, Carole; Lonjon, Pauline; Turan-Zitouni, Gülhan; Dzieciolowski, Julia; Becker, Katja; Bénard, Lionel; Condon, Ciaran; Maillard, Ludovic; Martinez, Jean; Frère, Jean-Marie; Dideberg, Otto; Galleni, Moreno; Docquier, Jean-Denis; Hernandez, Jean-François; ChemMedChem; vol. 12; nb. 12; (2017); p. 972 - 985 View in Reaxys With oxalyl dichloride, N,N-dimethyl-formamide in dichloromethane, Time= 4h, T= 0 - 20 °C , Inert atmosphere Sharma, Nidhi; Saha, Rajib; Parveen, Naziya; Sekar, Govindasamy; Advanced Synthesis and Catalysis; vol. 359; nb. 11; (2017); p. 1947 - 1958 View in Reaxys General Procedures for the Benzamide Substrates 14 General procedure: To a solution of the benzoic acid (3.66 mmol) and CH2Cl2 (5 mL) at 0 °C was added 3–5 drops of DMF. After effervescing subsided, oxalyl chloride (5.12 mmol) was added dropwise. After stirring at rt for 1 h, the reaction was concentrated in vacuo to give the acidchloride as an oil. It was taken back with CH2Cl2 (5 mL), cooled back 0 °C. A solution of2-aminophenyl-1H-pyrazole (3.29 mmol) in CH2Cl2 (5 mL) was added, followed bytriethylamine (3.66 mmol). The reaction was stirred at 0 °C for 10 min, and rt for 2 hwhen the reaction was judged complete by TLC, the reaction mixture was filtered. Thefiltrate was washed with saturated ammonium chloride, and brine, the organic layer wasdried over MgSO4, filtered and concentrated in vacuo. The residue was purified by flashchromatography eluting with Ethyl acetate/hexane (1:2) to give the desired benzamide 14. With oxalyl dichloride, N,N-dimethyl-formamide in dichloromethane, Time= 1h, T= 20 °C , Inert atmosphere Lee, Wan-Chen Cindy; Tehrani, Arya; Li, Jie Jack; Synthesis (Germany); vol. 49; nb. 13; (2017); p. 2865 - 2872 View in Reaxys With oxalyl dichloride, N,N-dimethyl-formamide in dichloromethane, Time= 12h, T= 0 - 20 °C , Inert atmosphere Parella, Ramarao; Babu, Srinivasarao Arulananda; Journal of Organic Chemistry; vol. 82; nb. 13; (2017); p. 6550 - 6567 View in Reaxys With oxalyl dichloride, N,N-dimethyl-formamide in dichloromethane, Time= 3h, T= 0 °C Taha, Taha Y.; Aboukhatwa, Shaimaa M.; Knopp, Rachel C.; Ikegaki, Naohiko; Abdelkarim, Hazem; Neerasa, Jayaprakash; Lu, Yunlong; Neelarapu, Raghupathi; Hanigan, Thomas W.; Thatcher, Gregory R. J.; Petukhov, Pavel A.; ACS Medicinal Chemistry Letters; vol. 8; nb. 8; (2017); p. 824 - 829 View in Reaxys 2. General procedure A: Preparation of 8-aminoquinolinyl amides General procedure: Synthesis of amides from the carboxylic acid: A 100 mL round bottom flask was charged with carboxylic acid (11 mmol) to which thionyl chloride (10 mL) was added dropwise under flow of argon at room temperature. The reaction mixture was refluxed for 3 h at 85 °C, then the excess SOCl2 was removed in vacuo to afford the crude acid chloride on one hand, whereas in another flask solution of 8-aminoquinoline (10 mmol) and NEt3 (11 mmol) in dichloromethane (20 mL) was stirred for 10-15 minutes. Deprotonated amine was added to a solution of acid chloride at 0 °C. The reaction was allowed to warm to room temperature and stirred overnight for complete conversion. Upon completion, it was quenched with saturated NaHCO3 solution and extracted with CH2Cl2 three times. These extracts were combined and dried over NaSO4. After evaporation in vacuum, the crude amide product was purified by flash column chromatography (Hexane: ethyl acetate 10:1) through silica gel. With thionyl chloride, Time= 3h, T= 20 - 85 °C , Inert atmosphere Kalsi, Deepti; Barsu, Nagaraju; Dahiya, Pardeep; Sundararaju, Basker; Synthesis (Germany); vol. 49; nb. 17; (2017); p. 3937 - 3944 View in Reaxys 2.8. N-(2-(2,6-dioxopiperidin-3-yl)-1-oxoisoindolin-4-yl)-2,2,2-trifluoroacetamide (2a)

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General procedure: Thionyl chloride (0.26 g, 2.1 mmol) was added to a solution of trifluoroacetate (0.26 g, 2 mmol) in DCM (10 mL). After the mixture was heated to reflux for 1h, it was concentrateed under reduced pressure to give a yellow oil.TEA (0.50 g, 5 mmol) was added to a solution of 10 (0.26 g, 1 mmol) in THF (20 mL), then the yellow oil in THF (10 mL) was added. The mixture was stirred at room tempreture for 6h, then H2O (1 mL) was added. After the start material was consumed which monitored by TLC, the mixture was concentrateed under reduced pressure. The residue was added 1N HCl (25 mL) and stirred for half an hour. Filter and wash the filter cake with water to yield 2a as a yellow solid. With thionyl chloride in dichloromethane, Time= 1h, Reflux Hu, Shengquan; Yuan, Libin; Yan, Hong; Li, Zhigang; Bioorganic and Medicinal Chemistry Letters; vol. 27; nb. 17; (2017); p. 4075 - 4081 View in Reaxys With oxalyl dichloride, N,N-dimethyl-formamide in dichloromethane, Time= 1h, T= 20 °C , Inert atmosphere Trifonov, Alexey L.; Levin, Vitalij V.; Struchkova, Marina I.; Dilman, Alexander D.; Organic Letters; vol. 19; nb. 19; (2017); p. 5304 - 5307 View in Reaxys General procedure: To a solution of phosphorus pentachloride (0.126 g, 0.610 mmol) in dichloromethane (11 mL), phenoxyacetic acid (0.092 g, 0.610 mmol) was added with stirring and the mixture refluxed for 30-40 minutes. After cooling, 4-methyl-1,2,5-oxadiazol-3-amine (0.060 g, 0.610 mmol) was added and the solution refluxed for 2-2.5 hours. The solvent was removed under reduced pressure and the residue quenched with water (50 mL). The solid was collected by vacuum filtration and washed with saturated sodium bicarbonate solution followed by water to afford compound 19 (0.103 g, 73percent) With phosphorus pentachloride in dichloromethane, Reflux Christoff, Rebecca M.; Murray, Gerald L.; Kostoulias, Xenia P.; Peleg, Anton Y.; Abbott, Belinda M.; Bioorganic and Medicinal Chemistry; vol. 25; nb. 24; (2017); p. 6267 - 6272 View in Reaxys

Rx-ID: 40278894 View in Reaxys 2/12 Yield

Conditions & References With bis(tri-t-butylphosphine)palladium(0), benzyltriphenylphosphonium chloride in toluene, Time= 24h, T= 110 °C , p= 15201Torr , Autoclave, Glovebox Quesnel, Jeffrey S.; Kayser, Laure V.; Fabrikant, Alexander; Arndtsen, Bruce A.; Chemistry - A European Journal; vol. 21; nb. 26; (2015); p. 9550 - 9555 View in Reaxys

H 2N N O

Rx-ID: 37348158 View in Reaxys 3/12 Yield

Conditions & References With oxalyl dichloride in dichloromethane, N,N-dimethyl-formamide Shang, Ming; Sun, Shang-Zheng; Dai, Hui-Xiong; Yu, Jin-Quan; Journal of the American Chemical Society; vol. 136; nb. 9; (2014); p. 3354 - 3357 View in Reaxys

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Rx-ID: 36713321 View in Reaxys 4/12 Yield

Conditions & References

98 %

With bis(tri-t-butylphosphine)palladium(0), benzyltriphenylphosphonium chloride in toluene, Time= 24h, T= 110 °C , p= 38002.6Torr , Glovebox, Autoclave, Inert atmosphere Quesnel, Jeffrey S.; Arndtsen, Bruce A.; Journal of the American Chemical Society; vol. 135; nb. 45; (2013); p. 16841 - 16844 View in Reaxys

Rx-ID: 6076740 View in Reaxys 5/12 Yield

Conditions & References Grekov; Trudy IREA; (1961); p. 131; ; vol. 58; nb. 3418a; (1963) View in Reaxys Ol'dekop; Kalinina; J. Gen. Chem. USSR (Engl. Transl.); vol. 34; (1964); p. 3473,3515 View in Reaxys Ol'dekop et al.; Doklady Chemistry; vol. 139; (1961); p. 862; Doklady Akademii Nauk SSSR; vol. 139; (1961); p. 1383 View in Reaxys Particular illustrative examples of acylation agents with formula (II) that can be cited are: acetic anhydride; ... crotonyl chloride; benzoyl chloride; p-nitrobenzoyl chloride; methoxybenzoyl chloride; naphthoyl chloride; Patent; Chimie, Rhodia; US6608232; (2003); (B1) English View in Reaxys A process according to claim 26, wherein the acylation agent is selected from the group consisting in: acetic anhydride; ... crotonyl chloride; benzoyl chloride; p-nitrobenzoyl chloride; methoxybenzoyl chloride; naphthoyl chloride; Patent; Chimie, Rhodia; US6608232; (2003); (B1) English View in Reaxys 15 : EXAMPLE 32 STR35 0.38 g (2 mmol) of naphthoyl chloride in 5 ml of CH2 Cl2 is added to 0.9 g (2 mmol) of amine d and 0.6 ml of triethylamine in 20 ml of dry CH2 Cl2, while cooling with ice. EXAMPLE 32 STR35 0.38 g (2 mmol) of naphthoyl chloride in 5 ml of CH2 Cl2 is added to 0.9 g (2 mmol) of amine d and 0.6 ml of triethylamine in 20 ml of dry CH2 Cl2, while cooling with ice. The mixture is subsequently stirred at 0° C. for 1 hour and left to stand overnight. Water is added, and the mixture is acidified and extracted several times with CH2 Cl2. The residue from the organic phase is purified by chromatography (SiO2, EtOAc/cyclohexane=3:1). 1 g (83percent) of "Example 32" is obtained. C38 H53 NO5 (603) MS: 610 (M+Li+)

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Patent; Hoechst Aktiengesellschaft; US5610151; (1997); (A1) English View in Reaxys Suitable acid halides include the following: ... o-methoxybenzoyl chloride, p-cyanobenzoyl chloride, p-toluoyl chloride, p-pentyloxybenzoyl chloride, 1-naphthoyl chloride, 2-naphthoyl chloride, p-iodobenzoyl chloride, 4-biphenylcarbonyl chloride, ... Patent; American Cyanamid Company; US4288592; (1981); (A1) English View in Reaxys

Rx-ID: 25033426 View in Reaxys 6/12 Yield

Conditions & References 12.a : Preparation of N-Cyanomethyl-1-naphthamide STR19 (a) a mixture of 17.2 g (0.1 mole) 1-naphthoic acid, 14 g (0.11 moles) oxalyl chloride, 150 ml methylene chloride and three drops DMF (dimethylformamide) were stirred for about 24 hours. The clear reaction mixture was stripped to give about 19.1 g of the 1-naphthoyl chloride as a brown liquid which was used in step (b) without further isolation. in dichloromethane Patent; Chevron Research Company; US4785019; (1988); (A1) English View in Reaxys

(v3)

Rx-ID: 6684327 View in Reaxys 7/12 Yield

Conditions & References T= 190 °C Zukerwanik et al.; Zhurnal Obshchei Khimii; vol. 29; (1959); p. 3295,3297; engl. Ausg. S. 3259, 3261 View in Reaxys

copper-powder Cl

Rx-ID: 6684328 View in Reaxys 8/12 Yield

Conditions & References T= 190 °C Zukerwanik et al.; Zhurnal Obshchei Khimii; vol. 29; (1959); p. 3295,3297; engl. Ausg. S. 3259, 3261 View in Reaxys

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FeBr2 Cl

Rx-ID: 6684329 View in Reaxys 9/12 Yield

Conditions & References T= 190 °C Zukerwanik et al.; Zhurnal Obshchei Khimii; vol. 29; (1959); p. 3295,3297; engl. Ausg. S. 3259, 3261 View in Reaxys

FeCl2 Cl

Rx-ID: 6684330 View in Reaxys 10/12 Yield

Conditions & References T= 190 °C Zukerwanik et al.; Zhurnal Obshchei Khimii; vol. 29; (1959); p. 3295,3297; engl. Ausg. S. 3259, 3261 View in Reaxys

Cl HO

Cl Cl

CuCl2

Cl O

HCl and CO and CO2

Cl Cl

Rx-ID: 6728599 View in Reaxys 11/12 Yield

Conditions & References T= 190 °C Zukerwanik et al.; Zhurnal Obshchei Khimii; vol. 29; (1959); p. 3295,3297; engl. Ausg. S. 3259, 3261 View in Reaxys

β-naphthoic acid chloride Cl

Rx-ID: 6076741 View in Reaxys 12/12 Yield

Conditions & References With carbon disulfide, aluminium trichloride Liebermann; Zsuffa; Chemische Berichte; vol. 44; (1911); p. 206 View in Reaxys

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