[CH3:1][C:2]1[CH:6]=[C:5]([CH2:7]Cl)[O:4][N:3]=1.[CH3:9][N:10]([CH3:21])[C:11]([N:13]([CH3:20])[C:14]1[S:15][C:16]([SH:19])=[N:17][N:18]=1)=[O:12].C(N(CC)CC)C>O1CCCC1>[CH3:9][N:10]([CH3:21])[C:11]([N:13]([CH3:20])[C:14]1[S:15][C:16]([S:19][CH2:7][C:5]2[O:4][N:3]=[C:2]([CH3:1])[CH:6]=2)=[N:17][N:18]=1)=[O:12]In a 100 ml round bottom flask were mixed 3-methyl-5-chloromethylisoxazole (1.5 g, 11 mmol), tetrahydrofuran (50 ml), 1,1,3-trimethyl-3-(5-mercapto-1,3,4-thiadiazol-2-yl) urea (2.5 g, 11 mmol) and triethylamine (5.1 g, 50 mmol). This was stirred at room temperature overnight. The reaction mixture was filtered and the solvent was stripped from the filtrate on a rotary evaporator. The residue was dissolved in dichloromethane and this was washed with water (2×60 ml) and the organic solution was dried over MgSO4. This was treated with decolorizing carbon, was filtered and the solvent was removed to give a pale tan oil which was dried in vacuo, 2.9 g, 84.1% yield. NMR: (CDCl3) 6.2 (S, 1H), 4.5 (S, 2H), 3.55 (S, 3H), 2.95 (S, 6H), 2.25 (S, 3H). IR (neat) 3120, 2960, 2930, 1660, 1600, 1480, 1440, 1410, 1370 1305, 1265, 1125, 1080, 1060 cm-1. Calcd: C, 42.16; H, 4.82; N, 22.35. Found: C, 42.06; H, 4.90; N, 22.10.
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