[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[C:9](=[N:11][OH:12])[CH3:10])=[CH:4][CH:3]=1.[NH2:14][NH:15][C:16]([NH2:18])=[S:17].CO>C(O)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[N:14][NH:15][C:16]([NH2:18])=[S:17])[C:9](=[N:11][OH:12])[CH3:10])=[CH:4][CH:3]=1A mixture of 4'-chloro-2-hydroxyiminopropiophenone (252.3 g), thiosemicarbazide (151.3 g), methanol (650 ml) water (300 ml), and acetic acid (9 ml) was refluxed for 31 hours with stirring. After cooling, the resulting precipitates were collected by filtration, washed successively with methanol, water and methanol, and then dried to give 4'-chloro-2-hydroxyiminopropiophenone thiosemicarbazone (298.88 g).
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