Synthesis of Isothiocyanates by Reaction of Amines with Phenyl Chlorothionoformate via One-Pot or Two-Step Process

Zheng-Yi Li; Hong-Zhao Ma; Chen Han; Hai-Tao Xi; Qi Meng; Xin Chen; Xiao-Qiang Sun

doi:10.1055/s-0033-1338744

Synthesis, Inhaltsverzeichnis

Synthesis 2013; 45(12): 1667-1674
DOI: 10.1055/s-0033-1338744

paper

Synthesis of Isothiocyanates by Reaction of Amines with Phenyl Chlorothionoformate via One-Pot or Two-Step Process

Zheng-Yi Li

^aJiangsu Key Laboratory of Fine Petrochemical Engineering, School of Petrochemical Engineering, Changzhou University, Changzhou, Jiangsu 213164, P. R. of China

,

Hong-Zhao Ma

^aJiangsu Key Laboratory of Fine Petrochemical Engineering, School of Petrochemical Engineering, Changzhou University, Changzhou, Jiangsu 213164, P. R. of China

,

Chen Han

^aJiangsu Key Laboratory of Fine Petrochemical Engineering, School of Petrochemical Engineering, Changzhou University, Changzhou, Jiangsu 213164, P. R. of China

,

Hai-Tao Xi

^aJiangsu Key Laboratory of Fine Petrochemical Engineering, School of Petrochemical Engineering, Changzhou University, Changzhou, Jiangsu 213164, P. R. of China

,

Qi Meng

^aJiangsu Key Laboratory of Fine Petrochemical Engineering, School of Petrochemical Engineering, Changzhou University, Changzhou, Jiangsu 213164, P. R. of China

,

Xin Chen*

^bSchool of Pharmaceutical & Life Sciences, Changzhou University, Changzhou, Jiangsu 213164, P. R. of China Fax: +86(519)86330251 eMail: xinchen@cczu.edu.cn eMail: xqsun@cczu.edu.cn

,

Xiao-Qiang Sun*

^aJiangsu Key Laboratory of Fine Petrochemical Engineering, School of Petrochemical Engineering, Changzhou University, Changzhou, Jiangsu 213164, P. R. of China

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Abstract

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Abstract

A facile and efficient synthesis of isothiocyanates from amines is described. This method involves the reaction of amines with phenyl chlorothionoformate in the presence of solid sodium hydroxide by either a one-pot process or a two-step approach. The one-pot process is useful for preparing alkyl and electron-rich aryl isothiocyanates, whereas the two-step approach is more versatile, working very well not only for alkyl and electron-rich aryl isothiocyanates, but also for highly electron-deficient aryl and heterocyclic isothiocyanates.

Key words

isothiocyanates - phenyl chlorothionoformate - amine - one-pot process - two-step approach

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