Ammonia → HCID 19020738, compound

Participants

Reaction Steps

0.40 g of trichloromethyl chloroformate was added to a solution of 1.00 g of 5-chloro-2-(2,3-dihydroxypropyl)-1,2-benzisoxazol-3-one (prepared as disclosed in Japanese Patent Application Kokai No. Sho. 55-83766) in 20 ml of dry tetrahydrofuran and the mixture was then stirred at room temperature for 30 minutes. After this, 0.42 g of triethylamine was added dropwise at 5° C., and the mixture was again stirred at the same temperature for 30 minutes. At the end of this time, 5.0 ml of 28% v/v aqueous ammonia were added, and the mixture was stirred at room temperature for 2 hours. It was then heated under reflux for an additional 3 hours. The reaction mixture was then concentrated by evaporation under reduced pressure, and the residue was dissolved in 100 ml of ethyl acetate, washed with a 10% w/v aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate. The solvent was then removed by distillation under reduced pressure, and the residue was purified by column chromatography through silica gel, eluted with ethyl acetate, to give 0.75 g (yield 64.1%) of the title compound as a colorless powder, melting at 161°-162° C.

Provenance & Evidence