Citation: Li Zhejian, Gao Bao, Huang Hanmin. Amidation of Acid Chlorides to Primary Amides with Ammonium Salts[J]. Chinese Journal of Organic Chemistry, ;2018, 38(6): 1431-1436. doi: 10.6023/cjoc201801034 shu

Amidation of Acid Chlorides to Primary Amides with Ammonium Salts

a.
College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014
b.
Hefei National Laboratory for Physical Sciences at the Microscale, Department of Chemistry, University of Science and Technology of China, Hefei 230026

Corresponding author: Huang Hanmin, hanmin@ustc.edu.cn
Received Date: 24 January 2018
Revised Date: 6 March 2018
Available Online: 8 June 2018
Fund Project: the Anhui Provincial Natural Science Foundation 1708085MB28the National Natural Science Foundation of China 21702197Project supported by the National Natural Science Foundation of China (Nos. 21672199, 21702197), the CAS Interdisciplinary Innovation Team, the Fundamental Research Funds for the Central Universities and the Anhui Provincial Natural Science Foundation (No. 1708085MB28)the National Natural Science Foundation of China 21672199

Figures(1)

A practical amidation reaction for the synthesis of primary amides is presented, in which the simple NH₄Cl was identified as a practical and convenient amine source. A series of aromatic and aliphatic acid chlorides were successfully compatible with this protocol, affording the corresponding amides in good to excellent yields, which provides a rapid and reliable approach to amides from simple starting materials. Introducing the appropriate N-methyl pyrrolidone (NMP) into the system as solvent and acid-binding reagent plays a key role to avoid the use of stoichiometric amounts of base.
- ammonium salts,
- amidation,
- primary amides,
- acid chlorides,
- N-methyl pyrrolidone
1. [1]
  (a) Constable, D. J. C. ; Dunn, P. J. ; Hayler, J. D. ; Humphrey, G. R. ; Leazer, J. L. Jr. ; Linderman, R. J. ; Lorenz, K. ; Manley, J. ; Pearlman, B. A. ; Wells, A. ; Zaks, A. ; Zhang, T. Y. Green Chem. 2007, 9, 411.
  (b) Montalbetti, C. A. G. N. ; Falque, V. Tetrahedron 2005, 61, 10827.
  (c) Ghose, A. K. ; Viswanadhan, V. N. ; Wendoloski, J. J. J. Comb. Chem. 1999, 1, 55.
2. [2]
3. [3]
  (a) Hirano, T. ; Uehara, K. ; Kamata, K. ; Mizuno, N. J. Am. Chem. Soc. 2012, 134, 6425.
  (b) Zhang, S. ; Xu, H. ; Lou, C. ; Senan, A. M. ; Chen, Z. ; Yin, G. Eur. J. Org. Chem. 2017, 2017, 1870.
  (c) Veisi, H. ; Maleki, B. ; Hamelian, M. ; Ashrafi, S. S. RSC Adv. 2015, 5, 6365.
  (d) Marcé, P. ; Lynch, J. ; Blacker, A. J. ; Williams, J. M. J. Chem. Commun. 2016, 52, 1436.
  (e) Ramón, R. S. ; Marion, N. ; Nolan, S. P. Chem. -Eur. J. 2009, 15, 8695.
4. [4]
  (a) Jagdmann, G. E. Jr. ; Munson, H. R. Jr. ; Gero, T. W. Synth. Commun. 1990, 20, 1203.
  (b) Griffin, J. ; Atherton, J. ; Page, M. I. J. Phys. Org. Chem. 2013, 26, 1032.
  (c) Arrizabalaga, P. ; Castan P. ; Laurent, J. -P. J. Am. Chem. Soc. 1984, 106, 4814.
  (d) Garcia, J. ; Gonzádez, J. ; Segura, R. ; Urpí, F. ; Vilarrasa, J. J. Org. Chem. 1984, 49, 3322.
5. [5]
  Khalafi-Nezhad, A.; Zare, A.; Parhami, A.; Rad, M. N. S.; Nejabat, G. R. Phosphorus, Sulfur Silicon Relat. Elem. 2007, 182, 657. doi: 10.1080/10426500601047214
6. [6]
  (a) Cui, Z. ; Ling, Y. ; Li, B. ; Li, Y. ; Rui, C. ; Cui, J. ; Shi, Y. ; Yang, X. Molecules 2010, 15, 4267.
  (b) Wang, L. ; Dai, F. -Y. ; Zhu, J. ; Dong, K. -K. ; Wang, Y. -L. ; Chen, T. J. Chem. Res. 2011, 35, 313.
  (c) Srinivasan, S. ; Manisankar, P. Synth. Commun. 2010, 40, 3538.
7. [7]
  (a) Kent, R. E. ; McElvain, S. M. Org. Synth. 1955, 3, 490.
  (b) Fisher, L. E. ; Caroon, J. M. ; Stabler, S. R. ; Lundberg, S. ; Zaidi, S. ; Sorensen, C. M. ; Sparacino, M. L. ; Muchowski, J. M. Can. J. Chem. 1994, 72, 142.
  (c) Keurulainen, L. ; Heiskari, M. ; Nenonen, S. ; Nasereddin, A. ; Kopelyanskiy, D. ; Leino, T. O. ; Yli-Kauhaluoma, J. ; Jaffe, C. L. ; Kiuru, P. Med. Chem. Commun. 2015, 6, 1673.
  (d) Fǎrcasiu, D. ; Jähme, J. ; Rüchardt, C. J. Am. Chem. Soc. 1985, 107, 5717.
8. [8]
  (a) Green, R. A. ; Hartwig, J. F. Org. Lett. 2014, 16, 4388.
  (b) Kim, J. ; Chang, S. Chem. Commun. 2008, 3052.
  (c) Suresh, A. S. ; Baburajan, P. ; Ahmed, M. Tetrahedron Lett. 2015, 56, 4864.
  (d) Wu, X. ; Wannberg, J. ; Larhed, M. Tetrahedron 2006, 62, 4665.
9. [9]
  (a) Della, E. W. ; Kasum, B. ; Kirkbride, K. P. J. Am. Chem. Soc. 1987, 109, 2746.
  (b) Ma, Y. ; Stivala, C. E. ; Wright, A. M. ; Hayton, T. ; Liang, J. ; Kersztes, I. ; Lobkovsky, E. ; Collum, D. B. ; Zakarian, A. J. Am. Chem. Soc. 2013, 135, 16853.
  (c) Sakharov, S. G. ; Kovalev, V. V. ; Gorbunova, Y. E. ; Tokmakov, G. P. ; Skabitskii, I. V. ; Kokunov, Y. V. Russ. J. Coord. Chem. 2017, 43, 75.
  (d) Caner, J. ; Vilarrasa, J. J. Org. Chem. 2010, 75, 4880.
10. [10]
  (a) Gao, B. ; Zhang, G. ; Zhou, X. ; Huang, H. Chem. Sci. 2018, 9, 380.
  (b) Zhang, G. ; Ji, X. ; Yu, H. ; Yang, L. ; Jiao, P. ; Huang, H. Tetrahedron Lett. 2016, 57, 383.
  (c) Hu, Y. ; Shen, Z. ; Huang, H. ACS Catal. 2016, 6, 6785.
  (d) Zhang, G. ; Gao, B. ; Huang, H. Angew. Chem., Int. Ed. 2015, 54, 7657.
11. [11]
  Liu, J.; Li, H.; Spannenberg, A.; Franke, R.; Jackstell, R.; Beller, M. Angew. Chem., Int. Ed. 2016, 55, 13544. doi: 10.1002/anie.201605104
12. [12]
  (a) Yamada, K. ; Karuo, Y. ; Tsukada, Y. ; Kunishima, M. Chem. -Eur. J. 2016, 22, 14042.
  (b) Liu, H. ; Laurenczy, G. ; Yan, N. ; Dyson, P. J. Chem. Commun. 2014, 50, 341.
  (c) Song, Q. ; Feng, Q. ; Yang, K. Org. Lett. 2014, 16, 624.
  (d) Ma, X. -Y. ; He, Y. ; Hu, Y. -L. ; Lu, M. Tetrahedron Lett. 2012, 53, 449.
  (e) Freudenreich, C. ; Samama, J. -P. ; Biellmann, J. -F. J. Am. Chem. Soc. 1984, 106, 3344.
  (f) Khrustalev, V. N. ; Sandhu, B. ; Bentum, S. ; Fonari, A. ; Krivoshein, A. V. ; Timofeeva, T. V. Cryst. Growth Des. 2014, 14, 3360.
  (g) Blanchette, J. A. ; Brown, E. V. J. Am. Chem. Soc. 1952, 74, 1066.
  (h) Movassagh, B. ; Rezaei, N. New J. Chem. 2015, 39, 7988.
  (i) Mol, M. D. Recl. Trav. Chim. Pays-Bas 1907, 26, 373.
  (j) Martínez-Asencio, A. ; Yus, M. ; Ramón, D. J. Tetrahedron 2012, 68, 3948.
1. [1]
  Ruilong Geng , Lingzi Peng , Chang Guo . Dynamic kinetic stereodivergent transformations of propargylic ammonium salts via dual nickel and copper catalysis. Chinese Chemical Letters, 2024, 35(8): 109433-. doi: 10.1016/j.cclet.2023.109433
2. [2]
  Xin Zhou , Xuejia Li , Yujia Xiang , Heng Zhang , Chuanshu He , Zhaokun Xiong , Wei Li , Peng Zhou , Hongyu Zhou , Yang Liu , Bo Lai . The application of low-valent sulfur oxy-acid salts in advanced oxidation and reduction processes: A review. Chinese Chemical Letters, 2025, 36(9): 110664-. doi: 10.1016/j.cclet.2024.110664
3. [3]
  Yuxin Wang , Zhengxuan Song , Yutao Liu , Yang Chen , Jinping Li , Libo Li , Jia Yao . Methyl functionalization of trimesic acid in copper-based metal-organic framework for ammonia colorimetric sensing at high relative humidity. Chinese Chemical Letters, 2024, 35(6): 108779-. doi: 10.1016/j.cclet.2023.108779
4. [4]
  Liangfeng Yang , Liang Zeng , Yanping Zhu , Qiuan Wang , Jinheng Li . Copper-catalyzed photoredox 1,4-amidocyanation of 1,3-enynes with N-amidopyridin-1-ium salts and TMSCN: Facile access to α-amido allenyl nitriles. Chinese Chemical Letters, 2024, 35(11): 109685-. doi: 10.1016/j.cclet.2024.109685
5. [5]
  Hefei Yang , Le-Cheng Wang , Xiao-Feng Wu . Sustainable carbonylative transformation of alkyl iodides to amides via crosslinking of EDA and XAT. Chinese Chemical Letters, 2025, 36(9): 110843-. doi: 10.1016/j.cclet.2025.110843
6. [6]
  Chengyao Zhao , Jingyuan Liao , Yuxiang Zhu , Yiying Zhang , Lianjie Zhai , Junrong Huang , Hengzhi You . Polystyrene-supported phosphoric-acid catalyzed atroposelective construction of axially chiral N-aryl benzimidazoles. Chinese Chemical Letters, 2025, 36(6): 110337-. doi: 10.1016/j.cclet.2024.110337
7. [7]
  Li Li , Zhi-Xin Yan , Chuan-Kun Ran , Yi Liu , Shuo Zhang , Tian-Yu Gao , Long-Fei Dai , Li-Li Liao , Jian-Heng Ye , Da-Gang Yu . Electro-reductive carboxylation of CCl bonds in unactivated alkyl chlorides and polyvinyl chloride with CO₂. Chinese Chemical Letters, 2024, 35(12): 110104-. doi: 10.1016/j.cclet.2024.110104
8. [8]
  Beitong Zhu , Xiaorui Yang , Lirong Jiang , Tianhong Chen , Shuangfei Wang , Lintao Zeng . A portable and versatile fluorescent platform for high-throughput screening of toxic phosgene, diethyl chlorophosphate and volatile acyl chlorides. Chinese Chemical Letters, 2025, 36(1): 110222-. doi: 10.1016/j.cclet.2024.110222
9. [9]
  Haoran Shi , Jiaxin Wang , Yuqin Zhu , Hongyang Li , Guodong Ju , Lanlan Zhang , Chao Wang . Highly selective α-C(sp³)-H arylation of alkenyl amides via nickel chain-walking catalysis. Chinese Chemical Letters, 2024, 35(7): 109333-. doi: 10.1016/j.cclet.2023.109333
10. [10]
  Huashan Huang , Jingze Chen , Luyun Zhang , Hong Yan , Siqi Li , Fen-Er Chen . Oscillatory flow reactor facilitates fast photochemical Wolff rearrangement toward synthesis of α-substituted amides in flow. Chinese Chemical Letters, 2025, 36(2): 109992-. doi: 10.1016/j.cclet.2024.109992
11. [11]
  Quanxing Mao , Zhengliang Wang , Zhinan Hu , Ziqi Yang , Hui Li , Yali Yao , Zijun Yong , Tianyi Ma . Facial detection of formaldehyde by using acidichromic carbon dots and the reaction between formaldehyde and ammonium chloride. Chinese Chemical Letters, 2025, 36(7): 110499-. doi: 10.1016/j.cclet.2024.110499
12. [12]
  Long TANG , Yaxin BIAN , Luyuan CHEN , Xiangyang HOU , Xiao WANG , Jijiang WANG . Syntheses, structures, and properties of three coordination polymers based on 5-ethylpyridine-2,3-dicarboxylic acid and N-containing ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1975-1985. doi: 10.11862/CJIC.20240180
13. [13]
  Jingtai Bi , Yupeng Cheng , Mengmeng Sun , Xiaofu Guo , Shizhao Wang , Yingying Zhao . Efficient and selective photocatalytic nitrite reduction to N₂ through CO₂ anion radical by eco-friendly tartaric acid activation. Chinese Chemical Letters, 2024, 35(11): 109639-. doi: 10.1016/j.cclet.2024.109639
14. [14]
  Peng Wang , Jianjun Wang , Ni Song , Xin Zhou , Ming Li . Radical dehydroxymethylative fluorination of aliphatic primary alcohols and diverse functionalization of α-fluoroimides via BF₃·OEt₂-catalyzed C‒F bond activation. Chinese Chemical Letters, 2025, 36(1): 109748-. doi: 10.1016/j.cclet.2024.109748
15. [15]
  Xiaojun Wang , Yizhou Zhang , Linwei Guo , Jianwei Li , Peng Wang , Lei Yang , Zhiming Liu . V₂CT_X MXene-derived ammonium vanadate with robust carbon skeleton for superior rate aqueous zinc-ion batteries. Chinese Chemical Letters, 2025, 36(8): 111231-. doi: 10.1016/j.cclet.2025.111231
16. [16]
  Jingtao Bi , Yupeng Cheng , Mengmeng Sun , Xiaofu Guo , Shizhao Wang , Yingying Zhao . Corrigendum to “Efficient and selective photocatalytic nitrite reduction to N₂ through CO₂ anion radical by eco-friendly tartaric acid activation” [Chinese Chemical Letters 35 (2024) 109639]. Chinese Chemical Letters, 2025, 36(7): 110867-. doi: 10.1016/j.cclet.2025.110867
17. [17]
  Rong-Nan Yi , Wei-Min He . Electron donor-acceptor complex enabled arylation of dithiocarbamate anions with thianthrenium salts under aqueous micellar conditions. Chinese Chemical Letters, 2024, 35(11): 110194-. doi: 10.1016/j.cclet.2024.110194
18. [18]
  Junxin Li , Chao Chen , Yuzhen Dong , Jian Lv , Jun-Mei Peng , Yuan-Ye Jiang , Daoshan Yang . Ligand-promoted reductive coupling between aryl iodides and cyclic sulfonium salts by nickel catalysis. Chinese Chemical Letters, 2024, 35(11): 109732-. doi: 10.1016/j.cclet.2024.109732
19. [19]
  Rong-Nan Yi , Wei-Min He . Visible light/copper catalysis enabled radial type ring-opening of sulfonium salts. Chinese Chemical Letters, 2025, 36(4): 110787-. doi: 10.1016/j.cclet.2024.110787
20. [20]
  Jiayu Li , Binli Wang , Yu Luo , Hongyu Wang , Lei Zhang . The double-sided roles of difluorooxalatoborate contained electrolyte salts in electrochemical energy storage devices: A review. Chinese Chemical Letters, 2025, 36(8): 110220-. doi: 10.1016/j.cclet.2024.110220

Get Citation

PDF

XML

Metrics

PDF Downloads(75)
Abstract views(3162)
HTML views(255)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142