Syntheses of 4 and 5-alkylsulfonylimidazoles

A series of isomeric 4 and 5-alkylsulfonyl, alkylsulfinylimidazoles 9,10 were prepared by two general methods. Chlorosulfonation of imidazole afforded 4(5)-chlorosulfonylimidazoles 2, 4, 5 . The chlorosulfonyl derivatives were reduced, alkylated and oxidized to give 9 and 10 . In the second method 2, 4, 5 were converted to sodium sulfinate 8 and reacted with alkyl halides to afford the title compound 9 .