Chinese Journal of Organic Chemistry ›› 2019, Vol. 39 ›› Issue (12): 3542-3549.DOI: 10.6023/cjoc201904063 Previous Articles     Next Articles

Special Issue: 二氧化碳合辑


桑国智, 冯雪童, 陈鹃, 李闪闪, 李卓娜, 李潇, 韩利民, 洪海龙, 竺宁   

  1. 内蒙古工业大学化工学院 内蒙古自治区CO2捕集与资源化工程技术研究中心 呼和浩特 010051
  • 收稿日期:2019-04-25 修回日期:2019-07-05 发布日期:2019-08-01
  • 通讯作者: 竺宁
  • 基金资助:

Synthesis of o-Halothiobenzamide Derivatives from the Selective Thiolysis Reaction of o-Halobenzonitrile Mediated by CO2

Sang Guozhi, Feng Xuetong, Chen Juan, Li Shanshan, Li Zhuona, Li Xiao, Han Limin, Hong Hailong, Zhu Ning   

  1. Inner Mongolia Engineering Research Center for CO2 Capture and Utilization, Chemical Engineering College, Inner Mongolia University of Technology, Hohhot 010051
  • Received:2019-04-25 Revised:2019-07-05 Published:2019-08-01
  • Supported by:
    Project supported by the National Natural Science Foundation of China (Nos. 21865020, 21362019), the Natural Science Foundation of Inner Mongolia (No. 2019LH02009), and the Program for Young Talents of Science and Technology in Universities of Inner Mongolia Autonomous Region (2019).

A method for the selective synthesis of o-halothiobenzamide by thiolysis reaction of o-halobenzonitrile with NaHS under the action of CO2 was explored. CO2/H2O/NaHS was used as a buffer system to provide a suitable pH environment, which would make HS- attack the nitrile-based carbon selectively to produce the corresponding o-halothiobenzamide. Moreover, the buffer system also provided the additionally required hydrogen atom for the thiolysis reaction of o-haloben-zonitrile with NaHS. Further studies have found that the CO2/Na2S·9H2O buffer system could also efficiently promote the thiolysis reaction of o-halobenzonitrile to form the corresponding o-halothiobenzamide. This synthetic method could be used to prepare different substituted o-halobenzonitriles, which is a simple, efficient and high atom-economic reaction.

Key words: halobenzonitriles, thiolysis reaction, halohiobenzamide, carbon dioxide, NaHS