Triethylamine → 1,2,3-Thiadiazole-5-methanol, 4-methyl-, 5-methanesulfonate

Participants

Reaction Steps

Under nitrogen atmosphere, 10.0 ml of triethylamine (72.6 m mol) and 4.1 ml of methanesulfonyl chloride (53 m mol) was added successively to a solution of 6.27 g of 5-hydroxymethyl-4-methyl-1,2,3-thiadiazole (48.16 m mol) in dichloromethane (50 ml) at −30° C. After stirring for 30 minutes, the mixture was poured into water-dichloromethane while the pH was kept between 8.5-9.0. The aqueous layer was separated, the organic layer was washed with saturated sodium hydrocarbonate, washed with dil-hydrochloric acid brine, dried over magnesium sulfate. After filtration, the filtrate was concentrated in vacuo to afford 5-methanesulfonyloxymethyl-4-methyl-1,2,3-thiadiazol (9.8 g).

Provenance & Evidence