[CH:1]1[C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([C:11]([OH:13])=O)[C:5]=2[CH:4]=[N:3][N:2]=1.[NH2:14][NH:15][C:16]([NH2:18])=[S:17]>CN(C=O)C>[CH:1]1[C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([C:11]([NH:14][NH:15][C:16]([NH2:18])=[S:17])=[O:13])[C:5]=2[CH:4]=[N:3][N:2]=1To a 100 mL round bottom flask was added phthalazine-5-carboxylic acid (0.50 g, 2.9 mmol) 1,1′-carbonyldiimidazole (0.93 g, 5.7 mmol) and DMF (2.2 mL). The mixture was stirred at 70° C. for 1 hour and treated with thiosemicarbazide (0.81 g, 8.9 mmol). The resulting mixture was stirred at 70° C. for 30 minutes. The mixture was concentrated under vacuum to remove almost all of the DMF. The remaining residue was treated with 2 N HCl with stirring until the solution reached pH 4. Upon standing, a yellow solid formed. The precipitate was recovered by filtration, washing with water and air dried to provide 1-(phthalazine-5-carbonyl)thiosemicarbazide (0.45 g, 63%).
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