Ammonia → HCID 19020721, compound

Participants

Reaction Steps

A solution of 10.0 g (37.0 mmoles) of 5-(m-chlorophenyl)-3-(2,3-dihydroxypropoxy)isoxazole [prepared as described in step (a) above] in 300 ml of dry tetrahydrofuran was cooled to 5° C., and then 3.96 g (20.0 mmoles) of trichloromethyl chloroformate were added dropwise to the mixture. The mixture was then stirred at 5°-6° C. for 30 minutes. At the end of this time, 4.04 g (40.0 mmoles) of triethylamine were added dropwise to the mixture at 5°-10° C., and the mixture was stirred at 3°-5° C. for 1 hour. 50 ml (400.0 mmoles) of 28% v/v aqueous ammonia were then added at one time, and the mixture was stirred at room temperature for a further 18 hours. The reaction mixture was then concentrated by evaporation under reduced pressure, and the resulting residue was diluted with 400 ml of ethyl acetate. The mixture was then washed with 400 ml of a 10% w/v aqueous solution of sodium chloride. The organic layer was dried over anhydrous magnesium sulfate, the desiccant was removed by filtration, and the solvent was removed by distillation under reduced pressure to give a solid residue. This solid residue was recrystallized from ethyl acetate, to give 8.30 g (yield 72.1%) of the title compound as colorless scales, melting at 149°-150° C.

Provenance & Evidence