2-氨基-5-溴-N,3-二甲基苯甲酰胺的电化学合成
Electrochemical Synthesis of 2-Amino-5-Bromo-N,3-Dimethylbenzamide

作者: 杨雷 , 王波 , 郑瀚骁 , 刘波 , 由君 , 吴绵园 :哈尔滨理工大学化学与环境工程学院,哈尔滨;黑龙江省高校绿色化工技术重点实验室,哈尔滨;

关键词: 电化学2-氨基-N3-二甲基苯甲酰胺2-氨基-5-溴-N3-二甲基苯甲酰胺Electrochemical 2-Amino-N3-Dimethylbenzamide 2-Amino-5-Bromo-N3-Dimethylbenzamide

摘要:

在单室电解池中,金属铂片为阴阳电极,稀硫酸为支持电解质,40%氢溴酸为反应物,THF为溶剂,室温,2-氨基-N,3-二甲基苯甲酰胺在1.3~2.0 V电压下恒电流电解可以高产率地合成2-氨基-5--N,3-二甲基苯甲酰胺。经反应条件优化,2-氨基-N,3-二甲基苯甲酰胺电化学溴化的最佳条件为:支持电解质为H2SO4,浓度为10%40%HBr用量为8.0 mL,电流密度0.4 A,在此条件下反应电压为1.32~1.65 V,溴化产物收率为97.3%,电流效率为88.3%

Abstract:
In a single-chamber electrolytic cell, platinum as the anode and cathode, dilute sulfuric acid as the supporting electrolyte, 40wt.% hydrobromic acid in H2O as the reactant, 2-amino-N,3-dimethylbe- nzamide can be highly synthesized into 2-amino-5-bromo-N,3-dimethylbenzamide by the constant- current electrolysis under the voltage from 1.3 V to 2.0 V at room temperature. The optimum of reaction conditions is as follows: electrolyte is H2SO4, the volume of hydrogen bromide is 8 mL, current density is 0.4 A, the reaction voltage is 1.32 - 1.65 V, product yield is 97.3% and the current efficiency was 88.3%.

文章引用: 杨雷 , 王波 , 郑瀚骁 , 刘波 , 由君 , 吴绵园 (2014) 2-氨基-5-溴-N,3-二甲基苯甲酰胺的电化学合成。 有机化学研究, 2, 18-22. doi: 10.12677/JOCR.2014.22003

参考文献

[1] 柴宝山, 何晓敏, 王军峰 (2010) 氰虫酰胺的合成与生物活性. 农药, 3, 1-3.

[2] Annis, G.D., Bruening, J. and Currie, M.J. (2008) Process for preparing 2-amino-5-cyanobenzoic acid derivatives. WO 2008082502A2.

[3] Finkelstein, B.L., Lahm, G.P. and Selby, T.P. (2004) Ortho-substituted aryl amides for controlling invertebrate pests. US 2004192731A1.

[4] 孙斌, 林雪 (2013) 2-氨基-5-氰基-N,3-二甲基苯甲酰胺合成方法改进. 化学研究与应用, 4, 599-603.

[5] Bruening, J., Casalnuovo, A.L. and Grushin, V. (2012) Process for preparing 2-amino-5-cyanobenzoic acid derivatives. WO2008070158A1.

[6] 乔庆东 (1995) 电化学有机合成. 抚顺石油学院学报, 1, 34-39.

[7] 张婷, 刘伟, 毛春晖 (2010) 2-氨基-5-氯-N,3-二甲基苯甲酰胺的合成工艺研究. 精细化工中间体, 5, 17-19.

[8] 秦伟艳, 刘波, 由君 (2012) “一锅法”合成2-氨基-N,3-二甲基-5-卤代苯甲酰胺. 有机化学, 32, 896-899.

[9] Matsuda, Y., Morita, M. and Yamamoto, H. (1985) Chlorination of poly(vinyltoluene) by electrolysis in an organic water suspension system. Bulletin of the Chemical Society of Japan, 58, 3413-3414.

[10] Raju, T., Muthukumaran, A. and Bashahme, D. (1996) Electrochemical reactor for preparation of monochlorotoluenes. Bulletin of Electrochemistry, 12, 322-323.

[11] Guseinov, A. and Inst, P.M. (2007) Study of kinetic principles of electroch-emicachlorination 1-acetylcyclohexane. Zerbaidzhanskii Khimicheskii Zhurnal, 1, 108-112.

[12] Ibrisagic, Z., Pletcher, D. and Brooks, W.N. (1985) Electrosynthesis in systems of two immiscible liquids and a phase transfer catalyst VI: The influence of zinc chloride on the chlorination of naphthalene. Journal of Applied Electrochemistry, 15, 719-725.

[13] Langer Sranley, H. and Yurchak, S. (1970) Electrogenerative chlorination. Journal of the Electrochemical Society, 117, 510-511.

[14] 马淳安, 著 (2002) 有机电化学合成导论. 北京科学出版社, 北京, 171-173.

分享
Top