Dimethyl Disulfide → HCID 86630963, compound

Participants

Reaction Conditions

Reaction Steps

(4-Methoxymethyl-thiazol-2-yl)-carbamic acid tert-butyl ester (840 mg, 3.4 mmol) was dissolved in dry THF (21 mL). At ˜−75° C. was added dropwise n-butyllithium solution 1.6 M in hexanes. (8.6 ml, 13.7 mmol). The dark-red mixture was stirred at ˜−75° C. for 30 min. At ˜−70° C. was then added dropwise methyl disulfide (970 mg, 10.3 mmol). The resultant yellow colored mixture was slowly warmed to rt and further stirred overnight. After quenching the reaction with saturated ammonium chloride solution, the organic layer was washed with brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure. After purification on silica gel with ethyl acetate and n-heptaene as eluents the title compound was obtained as a light yellow solid. (630 mg, 59%) MS (ISP): m/e 291.3 (M−H)+

Provenance & Evidence