Highly efficient synthesis of 2-mercaptobenzothiazole derivatives in water: metal sulfide-disulfide dynamic interchange reactionElectronic supplementary information (ESI) available: The detailed mechanism, LC-MS spectrometry, crystallographic details of S8, NMR spectra. See DOI: 10.1039/c6gc03053j

A convenient and efficient method for the synthesis of 2-mercaptobenzothiazoles from disulfide and CS 2 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 S 8 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 CS 2 . As a result, a novel synthetic route for the preparation of sulfur-containing heterocycles from a disulfide is developed. A convenient and efficient method for the synthesis of 2-mercaptobenzothiazoles from disulfide and CS 2 was performed by dynamic interchange reaction between a disulfide and a metal sulfide in water.