Triethylamine → HCID 13557232, compound

Participants

Reaction Steps

To a stirred solution of 3.0 grams (0.012 mole) of 2-(4-amino-2-chlorophenyl)methyl-4,4-dimethyl-3-isoxazolidinone and 1.2 grams (0.012 mole) of triethylamine in 30 ml of tetrahydrofuran was added dropwise 1.4 grams (0.013 mole) of cyclopropanecarboxylic acid chloride in 20 ml of tetrahydrofuran. During the addition the reaction mixture was cooled in an ice-water bath. Upon completion of addition the reaction mixture stirred for 16 hours; then was concentrated under reduced pressure to a residual solid. The solid was dissolved in 250 ml of methylene chloride. The solid was washed with water, which caused the precipitation of a solid that was insoluble in the liquid phases. The solid was removed by filtration. The organic phase was separated and washed with three 100 ml portions of water. The organic phase was dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to a residual solid. Both solids collected were subjected to thin layer chromatography and were determined to be the same material. The solids were combined and recrystallized from ethyl acetate/acetonitrile to give 2.5 grams of 2-[2-chloro-4-(cyclopropylcarbonylamino)phenyl]methyl-4,4-dimethyl-3-isoxazolidinone; m.p. 191°-193° C.

Provenance & Evidence