Water-Promoted Chlorination of 2-Mercaptobenzothiazoles was written by Wimmer, Laurin;Parmentier, Michael;Riss, Bernard;Kapferer, Tobias;Ye, Chao;Li, Lei;Kim, Hongyong;Li, Jialiang. And the article was included in Synthesis in 2018.Reference of 80945-83-1 This article mentions the following:
The substituted 2-mercaptobenzothiazoles were prepared (by reaction of 2-haloanilines and potassium o-Et carbonodithioate) and underwent chlorination using sulfuryl chloride/water so as to yield 2-chlorobenzothiazoles such as I [X = C, N; R = H, 6-Me, 7-Cl, etc.]. This straightforward and widely used reaction was impeded due to the poor reproducibility and low reaction yields. In this protocol, it was reported that the simple addition of water to the reaction lead to remarkable improvements in reaction efficiency because of the formation of acid through partial hydrolysis of sulfuryl chloride. The observations of improved yields were also obtained in the presence of some anhydrous acidic additives, but the simple combination of sulfuryl chloride and water reproducibly provided excellent yields for a range of chlorinated products I. In the experiment, the researchers used many compounds, for example, 2-Chlorobenzothiazole-6-carbonitrile (cas: 80945-83-1Reference of 80945-83-1).
2-Chlorobenzothiazole-6-carbonitrile (cas: 80945-83-1) belongs to thiazole derivatives. The thiazole ring is notable as a component of the vitamin thiamine (B1).Various laboratory methods exist for the organic synthesis of thiazoles. For example, 2,4-dimethylthiazole is synthesized from thioacetamide and chloroacetone.Reference of 80945-83-1
Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica