[F:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([F:12])[CH:11]=1)[CH2:5][N:6]=[C:7]=[S:8].[CH:13]([NH:15][NH2:16])=[O:14]>C(O)C>[F:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([F:12])[CH:11]=1)[CH2:5][NH:6][C:7](=[S:8])[NH:16][NH:15][CH:13]=[O:14]3,5-Difluorobenzyl isothiocyanate (9.9 g, 25.5 mmole) and formyl hydrazine (1.7 g, 28.7 mole) were refluxed in ethanol (30 ml) for one hour. The reaction was evaporated to dryness, triturated with hexane:ethyl acetate (1:1), filtered, and recrystallized from ethanol-hexane to yield 3.5 g (35%) of crude 4-(3',5'-difluorobenzyl)-1-formyl-3-thiosemicarbazide.
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