Cyanogen Bromide → HCID 178430968, compound

Participants

Reaction Steps

This compound is prepared by a combination of Schemes 1 and 4. Commercially available 2,6-dinitrotoluene is converted to 2,3-diamino-6-nitrotoluene according to scheme 2. Reaction with cyanogen bromide affords 2-amino-4-methyl-5-nitrobenzimidazole. After protection of the amino group with a tert-butoxycarbonyl group, the compound is reduced by hydrogenation (palladium-on-carbon) and brominated (bromine, sodium acetate, acetic acid) to afford 5-amino-6-bromo-2-tert-butoxycarbonylamino-4-methylbenzimidazole. The formation of the 5-(2-imidazolinylamino) group is completed in the usual fashion and the tert-butoxycarbonyl group is cleaved by treatment with hydrobromic acid to afford 2-amino-6-bromo-5-(2-imidazolinylamino)-4-methylbenzimidazole.

Provenance & Evidence