The Grignard condensation of N-methoxy-N-methylbenzamide (I) with 4-(methylsulfanyl)benzylmagnesium bromide (II) in THF gives the expected ketone (III), which is brominated with Br2 in CCl4 yielding the alpha-bromoketone (IV). The oxidation of the thioether group of (IV) with oxone (potassium peroxymonosulfate) in dichloromethane/methanol/tert-butanol/water affords the corresponding sulfone (V) (1), which is finally cyclocondesed with thiazol-2-amine (VI) in refluxing ethanol or isopentanol.
The Grignard condensation of N-methoxy-N-methylbenzamide (I) with 4-(methylsulfanyl)benzylmagnesium bromide (II) in THF gives the expected ketone (III), which is brominated with Br2 in CCl4 yielding the alpha-bromoketone (IV). The oxidation of the thioether group of (IV) with oxone (potassium peroxymonosulfate) in dichloromethane/methanol/tert-butanol/water affords the corresponding sulfone (V) (1), which is condesed with 4H-1,2,4-triazole-3-thiol (VI) in refluxing ethanol to give 2-[4-(methylsulfonyl)phenyl]-1-phenyl-2-(4H-1,2,4-triazol-3-ylsulfanyl)ethanone (VII). Finally, this compound is cyclized with polyphosphoric acid (PPA) in refluxing xylene.