Hydrochloric Acid → HCID 13557219, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2.0 grams (0.006 mole) of 2-[[2-chloro-4-(ethoxycarbonylamino)phenyl]methyl]-4,4-dimethyl-3-isoxazolidinone in 20 mL of chloroform was stirred under an argon atmosphere, and 1.1 mL (0.007 mole) of iodotrimethylsilane was added via syringe. The reaction mixture was heated to 60° C. where it was stirred for two hours. After this time the reaction mixture was warmed to 70° C. where it was stirred for 16 hours. The reaction mixture was cooled to ambient temperature, and 10 mL of methanolic 2N hydrochloric acid was added. The resultant clear solution was concentrated under reduced pressure, and the residue was slurried in 50 mL of water. An insoluble material was removed by filtration, and the filtrate was neutralized with an aqueous solution saturated with sodium bicarbonate. The mixture was extracted with methylene chloride, and the combined extracts were dried with magnesium sulfate. The mixture was filtered, and the filtrate was concentrated under reduced pressure to a solid residue. The solid was recrystallized from hexane-ethyl acetate to yield 0.4 gram of 2-[(4-amino-2-chlorophenyl)methyl]-4,4-dimethyl-3-isoxazolidinone; m.p. 105°-107° C.

Provenance & Evidence