Thionyl Chloride → N-benzylidene-4-trifluoromethylbenzenecarbohydrazonoyl chloride

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A mixture of N′-benzylidene-4-trifluoromethylbenzohydrazide (2.92 g), thionyl chloride (1.09 ml) and toluene (50 ml) was heated under reflux for 1 hr. After cooling, the reaction mixture was concentrated, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=8:1, volume ratio) and recrystallized from hexane to give N-benzylidene-4-trifluoromethylbenzenecarbohydrazonoyl chloride (1.85 g, yield 59%) as pale-yellow plate crystals. melting point: 95–96° C.

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