Hydrochloric Acid → 2-([4-[2-(4-Methanesulfonyloxyphenyl)ethoxy]phenyl]methyl) 1,2,4-oxadiazolidine-3,5-dione

Participants

Reaction Conditions

Reaction Steps

0.45 g (4 mmole) N-(chlorocarbonyl)isocyanate was added dropwise to a solution of 1.2 g (3.6 ml) 4-(2-{4-[hydroxyaminomethyl]phenoxy}ethyl)phenyl methanesulfonate in 20 ml anhydrous tetrahydrofuran at −5° C. and the mixture was stirred at −5° C. for 30 minutes. The reaction mixture was poured on to 2 M hydrochloric acid and extracted with ethyl acetate, dried (sodium sulfate), filtered and evaporated in vacuo. The residue was redissolved in ethyl acetate, and material that did not go into solution was filtered off. The filtrate was evaporated in vacuo, diethyl ether was added to give a white precipitate which was filtered off and recrystallized in diethyl ether/acetone to give 0.223 g of the desired product. The mother liquid was evaporated in vacuo and purified by chromatography on silica gel using dichloromethane:methanol (95:5) as eluent and crystallized in diethyl ether to give 0.09 g more of the desired product (total yield 0.384 g, 26.2%).

Provenance & Evidence