[OH-].[K+].[SH:3][C:4]1[S:8][C:7]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[S:16]([NH2:19])(=[O:18])=[O:17])=[N:6][N:5]=1.[CH3:20]I>CO>[CH3:20][S:3][C:4]1[S:8][C:7]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[S:16]([NH2:19])(=[O:18])=[O:17])=[N:6][N:5]=1To a solution containing 1.0 g of potassium hydroxide in 50 ml of methanol was added 5 g of the crude oxadiazole prepared in Example 2. After stirring about five minutes, 3.5 g of methyl iodide was added. The solution was refluxed one hour, cooled to 30°, an extra 10 ml of methyl iodide was added, and the solution was refluxed an additional two hours, then concentrated in vacuo. After water (about 150 ml) was added to the residue, the suspension was extracted with methylene chloride. The methylene chloride solution was dried (MgSO4), concentrated in vacuo, and the residue was recrystallized from acetonitrile to give 0.8 g of the subject compound; m.p. 175°-178° C. NMR(CDCl3, DMSO-d6): δ 2.8(s, SCH3); 4.9(s, CH2); 7.3(s, NH2); 7.4-8.3 (m, ar) ppm. Mass spectrum by direct probe using electron impact ionization showed highest significant m/e 301.
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