Abstract
I-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.
Similar content being viewed by others
References
A. F. Pozharskii, I. M. Nanavyan, and V. V. Kuz'menko,Mendeleev Commun., No. 1, 33 (1992).
A. F. Pozharskii, O. V. Dyablo, A. V. Belyaev, Z. A. Starikova, and A. I. Yanovskii,Tetrahedron,54, 9677 (1998).
O. V. Dyablo, A. F. Pozharskii, and V. V. Kuz'menko,Izv. Russ. Akad. Nauk, Ser. Khim., No. 11, 2231 (1995).
Additional information
Rostov State University, Rostov-on-Don 344090, Russia. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1404–1407, October, 1999.
Rights and permissions
About this article
Cite this article
Dyablo, O.V., Pozharskii, A.F. Synthesis of 2-azido-1-methyl-aminobenzimidazole. Chem Heterocycl Compd 35, 1222–1224 (1999). https://doi.org/10.1007/BF02323382
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF02323382