Citation: 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. doi: 10.6023/cjoc201904063 shu

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

Inner Mongolia Engineering Research Center for CO₂ Capture and Utilization, Chemical Engineering College, Inner Mongolia University of Technology, Hohhot 010051

Corresponding author: Zhu Ning, zhuning2622@yahoo.com
Received Date: 25 April 2019
Revised Date: 5 July 2019
Available Online: 1 December 2019
Fund Project: the Natural Science Foundation of Inner Mongolia 2019LH02009Project 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)the National Natural Science Foundation of China 21362019the National Natural Science Foundation of China 21865020

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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.
- halobenzonitriles,
- thiolysis reaction,
- halohiobenzamide,
- carbon dioxide,
- NaHS
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Synthesis of o-Halothiobenzamide Derivatives from the Selective Thiolysis Reaction of o-Halobenzonitrile Mediated by CO2

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通讯作者: 陈斌, bchen63@163.com

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