Jump to main content
Jump to site search
PLANNED MAINTENANCE Close the message box

Scheduled maintenance work on Wednesday 22nd May 2019 from 11:00 AM to 1:00 PM (GMT).

During this time our website performance may be temporarily affected. We apologise for any inconvenience this might cause and thank you for your patience.


Issue 4, 2017
Previous Article Next Article

Highly efficient synthesis of 2-mercaptobenzothiazole derivatives in water: metal sulfide–disulfide dynamic interchange reaction

Author affiliations

Abstract

A convenient and efficient method for the synthesis of 2-mercaptobenzothiazoles from disulfide and CS2 mediated by a metal sulfide in water is described. This synthetic methodology could be used to prepare diverse 2-mercaptobenzothiazole derivatives in good to excellent yields. In this paper, the concept of metal sulfide–disulfide dynamic interchange reaction was put forward. Then the intermediates of the interchange reaction between NaHS and a disulfide were detected by LC-MS, which demonstrated that the S–S bond of the disulfide could be broken by the metal sulfide through the dynamic interchange reaction. In addition, NaHS was eventually transformed into sulfur S8 by the dynamic interchange reaction. Moreover, the underlying mechanism of 2-mercaptobenzothiazole formation is proposed, in which NaHS not only acts as an S–S bond cleaving agent but also as an activator of CS2. As a result, a novel synthetic route for the preparation of sulfur-containing heterocycles from a disulfide is developed.

Graphical abstract: Highly efficient synthesis of 2-mercaptobenzothiazole derivatives in water: metal sulfide–disulfide dynamic interchange reaction

Back to tab navigation

Supplementary files

Publication details

The article was received on 06 Nov 2016, accepted on 02 Jan 2017 and first published on 03 Jan 2017


Article type: Paper
DOI: 10.1039/C6GC03053J
Green Chem., 2017,19, 1102-1108

  •   Request permissions

    Highly efficient synthesis of 2-mercaptobenzothiazole derivatives in water: metal sulfide–disulfide dynamic interchange reaction

    C. Lou, N. Zhu, R. Fan, H. Hong, L. Han, J. Zhang and Q. Suo, Green Chem., 2017, 19, 1102
    DOI: 10.1039/C6GC03053J

Search articles by author

Spotlight

Advertisements