(Chlorothio)formyl chloride → 5-(alpha,alpha,alpha,alpha',alpha',alpha'-Hexafluoro-3,5-xylyl)-1,3,4-oxathiazol-2-one

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Reaction Steps

3,5-Bis(trifluoromethyl)benzamide (60.5 g, 0.235 mol) and five equivalents of chlorocarbonylsulfenyl chloride (154 g, 1.175 mol) were heated in 600 ml of toluene at reflux, with stirring, for 12 hours. The crude product, a dark brown oil, weighed 77.5 g. After decolorization in hexane, the material was taken up in methanol and recrystallized three times to give 22.0 g (0.0699 mol, 29.75%) of pale gold solid, m.p. 61°-62.5°.

Provenance & Evidence