[CH3:1][N:2]1[C:6]([C:7]2[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=2)=[N:5][NH:4][C:3]1=[S:13].[CH3:14]I.[OH-].[Na+].O>CC(C)=O>[CH3:1][N:2]1[C:3]([S:13][CH3:14])=[N:4][N:5]=[C:6]1[C:7]1[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=1To a mechanically stirred and cooled (9° C.) suspension of 4-methyl-5-pyridin-4-yl-2,4-dihydro-3H-1,2,4-triazole-3-thione (267 g) and methyl iodide (197.7 g) in acetone (2.6 L), was added a solution of sodium hydroxide (54 g in 600 mL of water) at such a rate (ca. 20 mL/min) as to maintain the temperature between 10 and 15° C. Another portion of water (50 mL) was then added and the temperature was allowed to come to 21 to 24° C. After another 2 h, the acetone was distilled off from the reaction mixture in vacuo (water-bath kept at 30° C.). Another portion of water (750 mL) was then added before cooling (17 to 18° C.) and collection of the formed precipitate by filtration. This solid was then washed with water (2×1 L) before drying at 100 mbar under a gentle stream of air for 3 days to yield 235 g of the title compound as a white powder. 1H NMR (DMSO-d6): 2.7 (s, 3H), 3.6 (s, 3H), 7.7 (m, 2H), 8.8 (d, 2H).
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