Water → HCID 13192589, compound

Participants

Reaction Steps

To a stirred solution of 2.6 grams (0.009 mole) of 5-chloro-2-[(2-chlorophenyl)methyl]-4,4-dimethyl-3-isoxazolidinone (Example 23(A)) in 25 ml of tetrahydrofuran was added dropwise to a solution of 1.8 grams (0.019 mole) of aniline in 5 ml of tetrahydrofuran. Upon completion of addition the reaction mixture was heated under reflux for 4 hours; thin layer chromatography of the reaction mixture indicated the presence of starting 5-chloro compound. The reaction mixture was heated under reflux for an additional 60 hours; thin layer chromatography of the mixture again indicated the 5-chloro starting material to be present. The tetrahydrofuran solvent was removed by evaporation under reduced pressure and 0.9 gram (1 equiv.) of aniline in 20 ml of dimethylformamide was added. The solution was heated at 110°-120° for six hours, and was allowed to cool to ambient temperature where it was stirred for 18 hours. The reaction mixture was poured into 100 ml of water and extracted with three 50-ml portions of methylene chloride. The combined extracts were washed with two 50-ml portions of an aqueous solution of 5% hydrochloric acid. The organic layer was dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to give an oil residue. The residue was subjected to column chromatography on silica gel using 30% ethyl acetate in heptane. The appropriate fractions were combined and concentrated under reduced pressure to give 1.8 grams of 2-[(2-chlorophenyl)methyl]-4,4-dimethyl-5-phenylamino-3-isoxazolidinone; mp 99°-101°.

Provenance & Evidence