Process for removing sulfonyl groups from benzimidazole isomers

Details Process for removing sulfonyl groups from benzimidazole isomers Process for removing sulfonyl groups from benzimidazole isomers

C - Chemistry, Metallurgy

07

D

260/305.05, 260/

C07D 235/30 (2006.01) C07D 409/06 (2006.01)

Patent

CA 1187889

ABSTRACT OF THE DISCLOSURE This invention concerns a process for re- moving a sulfonyl group from the l-position of a benzimidazole to allow conversion of 2-amino-1,5- substituted-benzimidazole compounds into 2-amino- 1,6-substituted-benzimidazole compounds. The 5-isomer is reacted with an alkali metal hydroxide or carbonate in an inert aqueous organic solvent system. The reac- tion mixture is acidified to precipitate the base and form the intermediate benzimidazole tautomer. The intermediate is then reacted with a sulfonyl acylating agent or a haloalkyl isothiocyanate to form a mixture of 2-amino-1,5(6)-substituted-benzimidazole compounds. This invention also concerns the process for removing a sulfonyl group from the l-position of a benzimidazole to allow conversion of 2-amino-1,6-substituted-benz- imidazole compounds into 2-amino-1,5-substituted- benzimidazole compounds.

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