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

doi:10.6023/cjoc201904063

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

CO₂调控邻卤苯腈硫解选择性合成邻卤硫代苯甲酰胺类衍生物

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

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 E-mail:zhuning2622@yahoo.com
基金资助:
国家自然科学基金（Nos.21865020，21362019）、内蒙古自然科学基金（No.2019LH02009）和2019年度内蒙古自治区高等学校“青年科技英才支持计划”资助项目.

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

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).

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Abstract

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

Cite this article

Sang Guozhi, Feng Xuetong, Chen Juan, Li Shanshan, Li Zhuona, Li Xiao, Han Limin, Hong Hailong, Zhu Ning. Synthesis of o-Halothiobenzamide Derivatives from the Selective Thiolysis Reaction of o-Halobenzonitrile Mediated by CO₂[J]. Chinese Journal of Organic Chemistry, 2019, 39(12): 3542-3549.

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CO₂调控邻卤苯腈硫解选择性合成邻卤硫代苯甲酰胺类衍生物

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

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CO2调控邻卤苯腈硫解选择性合成邻卤硫代苯甲酰胺类衍生物