[NH2:1][C:2]1[CH:13]=[CH:12][C:11]([I:14])=[CH:10][C:3]=1[C:4]([NH:6][CH2:7][CH2:8][CH3:9])=[O:5].[C:15](=S)=[S:16].C(=O)([O-])[O-].[K+].[K+].Cl>CN(C)C=O>[I:14][C:11]1[CH:10]=[C:3]2[C:2](=[CH:13][CH:12]=1)[NH:1][C:15](=[S:16])[N:6]([CH2:7][CH2:8][CH3:9])[C:4]2=[O:5]
To a solution of 2-amino-5-iodo-N-propylbenzamide (1.0 g, 3.1 mmol) and carbon disulfide (0.59 g, 9.38 mmol) in dimethylformamide (3.1 mL) was added potassium carbonate (0.43g, 3.1 mmol). The reaction mixture was heated to reflux for 2 h, cooled to room temperature, and added dropwise to 1N hydrochloric acid (25 mL). The resulting precipitate was filtered, washed with water (2×10 mL), methanol (2×10 mL) and diethyl ether (10 mL), and dried to deliver 1.04 g of the title compound, m.p. 267-269° C.; 1H NMR (300 MHz, Me2SO-d6): δ0.90 (t,3H); 1.68 (m,2H); 4.33 (t,2H); 7.18 (d,1H); 8.04 (dd,1H); 8.19 (d, 1H); 12.98 (s, 1H).
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