[S-:1][C:2]#[N:3].[NH4+].[C:5](Cl)(=[O:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[Cl:14][C:15]1[C:23]2[C:19](=[N:20][S:21][N:22]=2)[CH:18]=[CH:17][C:16]=1[NH2:24]>CC(C)=O.CO>[C:5]([NH:3][C:2]([NH:24][C:16]1[CH:17]=[CH:18][C:19]2=[N:20][S:21][N:22]=[C:23]2[C:15]=1[Cl:14])=[S:1])(=[O:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1The starting material is obtained as follows: A solution of 6 g ammonium thiocyanate in 200 ml acetone is treated with 7 ml benzoyl chloride and stirred for 10 minutes. To this solution 6 g of 4-chloro-5-amino-2,1,3-benzothiadiazole in 200 ml of methanol is added. The mixture is boiled for 2 hours and cooled yielding N-benzoyl-N'-(4-chloro-2,1,3-benzothiadiazol-5-yl)thiourea (M.Pt. 220°-222° from methanol). The precipitate was filtered off and quickly heated to reflux with 100 ml of a 2 N aqueous solution of sodium hydroxide.
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