4-Hydroxy-6-methylthieno[2,3-b] thiopyran-2-sulfonamide,a intermediate of dorzolamide hydrochloride was synthesized from 2-mercaptothiophene and crotonic acid.Through addition to 3-(2-mercaptothiophene)butanoic acid.Through cycloration by phosphorus pentoxide,5,6-dihydro-6-methyl-4H-thieno[2,3-b] thiopyrane-4-one was prepared.Through chlorosulfonylation by chlorosulfonic acid and amination by ammonium hydroxide,finally,5,6-dihydro-6-methyl-4H-thieno[2,3-b] thiopyrane-4-one-2-sulfonamide was produced.Sodium borohydride,its overall yield was 16.0%.The chemical structure was confirmed by IR,1H NMR,MS.

This study successfully synthesized 4-hydroxy-6-methylthieno[2,3-b] thiopyran-2-sulfonamide, an intermediate in dorzolamide hydrochloride, with a yield of 16.0%.

Paper

Synthesis of 4-hydroxy-6-methylthieno[2,3-b] thiopyran-2-sulfonamide

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