Water → methyl 3-cyano-4-(1H-1,2,4-triazol-1-yl)-N-[(trimethylsilyl)methyl]benzenecarbimidothioate

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-cyano-4-(1H-1,2,4-triazol-1-yl)-N-[(trimethylsilyl)methyl]benzene-carbothioamide (1.5 g) in THF was added t-BuOK (0.64 g) under cooling (0° C.). After stirring for 15 minutes, methyl iodide (0.81 g) was added dropwise to the mixture under cooling (0° C.). The reaction liquor was returned to room temperature and stirred for 2 hours. Water was added to the reaction mixture, and aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution, subsequently dried over magnesium sulfate. After filtering the reaction mixture, the solvent was distilled off under reduced pressure, and the resulting mixture was purified by silica gel chromatography, to obtain methyl 3-cyano-4-(1H-1,2,4-triazol-1-yl)-N-[(trimethylsilyl)methyl]benzenecarbimidothioate at a yield of 64%.

Provenance & Evidence