[CH3:1][N:2]1[C:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:5][N:4]=[C:3]1[SH:13].O.[CH3:15]I>[OH-].[Na+].CCO>[CH3:1][N:2]1[C:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:5][N:4]=[C:3]1[S:13][CH3:15]To a solution of 4-methyl-5-phenyl-4H-1,2,4-triazole-3-thiol (2.00 g, 10 mmol) in NaOH 1.0 M in H2O (21 ml, 21 mmol) was added a solution of CH3I (0.98 mL, 16 mmol) in 6 mL EtOH. The reaction became cloudy and then clear. After 15 min, a white solid precipitated out of the reaction. The reaction was filtered, rinsing with water. The solid was collected and dried in vacuo to give 4-methyl-3-(methylthio)-5-phenyl-4H-1,2,4-triazole as a white solid. MS m/z=206 [M+H]+. Calc'd for C10H11N3S: 205.3.
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