C(Cl)(Cl)=O.[NH2:5][C:6]1[S:7][CH:8]=[C:9]([CH3:21])[C:10]=1[S:11]([NH:14][C:15]([NH:17][CH:18]([CH3:20])[CH3:19])=S)(=[O:13])=[O:12].C(N(CC)CC)C.C(OCC)(=O)C>C1(C)C=CC=CC=1.C1COCC1>[CH:18]([NH:17][C:15]1[NH:5][C:6]2[S:7][CH:8]=[C:9]([CH3:21])[C:10]=2[S:11](=[O:13])(=[O:12])[N:14]=1)([CH3:20])[CH3:19]A 20% solution of phosgene in toluene (715 μl) was added to a stirred and cooled solution of N-(2-amino-4-methyl-3-thienylsulfonyl)-N′-isopropylthiourea (0.22 g) and triethylamine (313 μl) in dry THF (5 ml) the temperature being kept below 5° C. After stirring for 1.5 h the mixture was evaporated and triturated with 10 ml of water. The precipitate was collected by filtration and dried to give 0.14 g of crude product. The crystals were heated at 70° C. with 5 ml of ethyl acetate and the resulting mixture was cooled to 0° C. for 10 min and then filtered. The filter cake was rinsed with a minute amount of ethyl acetate and dried to give 0.087 g (yield 45%) of the title compound as tan crystals; m.p. 152-154° C.; 1H-NMR (DMSO-d6): δ(ppm): 7.10 (br d, 1 H, NH), 6.61 (s, 1 H, N(4)H), 6.52 (s, 1 H, C(6)H), 3.89 (m, 1 H, CH), 2.32 (s, 3 H, CH3), 1.18 (d, 6 H, CH3).
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