[NH2:1][NH:2][C:3]([NH2:5])=[S:4].C(O)(=O)C.[C:10]([NH:13][C:14]1[CH:21]=[CH:20][C:17]([CH:18]=O)=[CH:16][C:15]=1[Cl:22])(=[O:12])[CH3:11]>O.C(O)C>[C:10]([NH:13][C:14]1[CH:21]=[CH:20][C:17]([CH:18]=[N:1][NH:2][C:3]([NH2:5])=[S:4])=[CH:16][C:15]=1[Cl:22])(=[O:12])[CH3:11]A solution of 0.73 g (0.008 mole) of thiosemicarbazide (Aldrich T3,340-5) in 24 mL of water containing 1.6 mL of glacial acetic acid was added to a solution of 1.58 g of (0.008 mole) 4-acetamido-3-chlorobenzaldehyde (24) in 20 mL of ethanol at 70°. The mixture was stirred at this temperature for 45 minutes. A white precipitate developed in the reaction mixture, which was filtered after cooling to give 1.95 g (90%) of 25 as off white crystals, mp 235-2380°. Infrared (IR) and NMR analysis gave the following results: IR (potassium bromide): 3423, 3260, 3132, 1701 (C=O), 1594, 1508, 1303 cm−1. 1H nmr (90 MHz, DMSO-d6):δ 11.47 (1 H, s, thiosemicarbazone NH), 9.35 (1 H, s, amide NH), 8.15-7.91 (5H; m; H-2, H-5, imine H and thiosemicarbazone NH2), 7.6 (1H; dd, 3JH5-H6=8.1 Hz, 4JH2-H6=1.8 Hz; H-6) 2.18 (3H, s, CH3). Anal. Calcd. for C10H11CIN4OS (270.73): C, 44.36; H, 4.10; Cl, 13.10; N, 20.69; S, 11.84. Found: C, 44.51; H, 4.14; Cl, 12.91; N, 20.67; S, 12.27.
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