m-Toluamide → 5-(3-Methylphenyl)-2H-1,3,4-oxathiazol-2-one

Participants

Reaction Steps

m-Toluamide (116 g, 0.86 mol) and chlorocarbonylsulfenyl chloride (144 g, 1.1 mol, 28% excess) were heated to 100° C. in 400 ml of toluene, with stirring, for 5.5 hours. Cooling resulted in an orange solid. The solid, isolated by filtration, was dissolved in hot methylcyclohexane and decolorized. The light yellow product was recrystallized once from methyl-cyclohexane to give 76.05 g (45.8%) of white solid, m.p. 82. 5°-84°.

Provenance & Evidence