Synthesis 2013; 45(12): 1667-1674
DOI: 10.1055/s-0033-1338744
paper
© Georg Thieme Verlag Stuttgart · New York

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

Zheng-Yi Li
a   Jiangsu Key Laboratory of Fine Petrochemical Engineering, School of Petrochemical Engineering, Changzhou University, Changzhou, Jiangsu 213164, P. R. of China
,
Hong-Zhao Ma
a   Jiangsu Key Laboratory of Fine Petrochemical Engineering, School of Petrochemical Engineering, Changzhou University, Changzhou, Jiangsu 213164, P. R. of China
,
Chen Han
a   Jiangsu Key Laboratory of Fine Petrochemical Engineering, School of Petrochemical Engineering, Changzhou University, Changzhou, Jiangsu 213164, P. R. of China
,
Hai-Tao Xi
a   Jiangsu Key Laboratory of Fine Petrochemical Engineering, School of Petrochemical Engineering, Changzhou University, Changzhou, Jiangsu 213164, P. R. of China
,
Qi Meng
a   Jiangsu Key Laboratory of Fine Petrochemical Engineering, School of Petrochemical Engineering, Changzhou University, Changzhou, Jiangsu 213164, P. R. of China
,
Xin Chen*
b   School 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*
a   Jiangsu Key Laboratory of Fine Petrochemical Engineering, School of Petrochemical Engineering, Changzhou University, Changzhou, Jiangsu 213164, P. R. of China
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Publikationsverlauf

Received: 26. März 2013

Accepted after revision: 16. April 2013

Publikationsdatum:
08. Mai 2013 (online)


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.

Supporting Information