[OH-].[Na+].[CH3:3]I.[OH:5][C:6]1[CH:11]=[CH:10][C:9]([N:12]2[C:16]([SH:17])=[N:15][N:14]=[N:13]2)=[CH:8][CH:7]=1>O.O1CCCC1.[Cl-].[Na+].O>[CH3:3][S:17][C:16]1[N:12]([C:9]2[CH:10]=[CH:11][C:6]([OH:5])=[CH:7][CH:8]=2)[N:13]=[N:14][N:15]=1A solution of sodium hydroxide (2.06 g) in water (120 ml) followed by methyl iodide (3.5 ml) was added to a solution of 1-(4-hydroxyphenyl)-1H-tetrazole-5-thiol (10 g) in tetrahydrofuran (30 ml) and stirred at room temperature for 5 h. The mixture was poured into brine (120 ml), extracted with ethyl acetate (3×60 ml), dried (Na2 SO4) and evaporated to give the title compound as a brown solid (10.64 g). T.l.c. (Dichloromethane/methanol (990:10)), Rf=0.42
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