SYNTHESIS OF 2-AZIDO-1-METHYLAMINOBENZIMIDAZOLE

Abstract

1-Methylamino-2-hydrazinobenzimidazole was synthesized by the sequential action of hydrogen peroxide and hydrazine hydrate on 1-(acetylmethylamino)benzimidazoline-2-thione. Nitrosation of the former with nitrous acid led to 2-azido-1-(nitrosomethylamino)benzimidazole, which exists as a mixture of s-cis and s-trans conformers with hindered rotation about the N–NO bond. 2-Azido-1-methylaminobenzimidazole was obtained by treatment of the nitrosation product with conc. hydrochloric acid.

Authors: O. V. Dyablo and A. F. Pozharskii.

English Translation in Chemistry of Heterocyclic Compounds, 1999, 35 (10), pp 1222-1224

http://link.springer.com/article/10.1007/BF02323382