Dichloromethane → HCID 15052042, compound

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[C:13](=[O:14])[C:12]([CH3:16])([CH3:15])[CH2:11][O:10]2)=[C:4]([Cl:17])[CH:3]=1.[C:18]1(=O)[O:23][C:21](=[O:22])[C:20]2[CH2:24][CH2:25][CH2:26][CH2:27][C:19]1=2.C(Cl)Cl>C(O)(=O)C>[Cl:17][C:4]1[CH:3]=[C:2]([N:1]2[C:21](=[O:22])[C:20]3[CH2:24][CH2:25][CH2:26][CH2:27][C:19]=3[C:18]2=[O:23])[CH:7]=[CH:6][C:5]=1[CH2:8][N:9]1[C:13](=[O:14])[C:12]([CH3:15])([CH3:16])[CH2:11][O:10]1

Participants

Procedure

A solution of 2.0 grams (0.008 mole) of 2-[(4-amino-2-chlorophenyl)methyl]-4,4-dimethyl-3-isoxazolidinone and 1.2 grams (0.008 mole) of 3,4,5,6-tetrahydrophthalic anhydride in 20 mL of acetic acid was stirred at ambient temperature for four hours and then was heated under reflux for six hours. The cooled reaction mixture was poured into 300 mL of methylene chloride and was washed in turn with two 100 mL portions of water, two 50 mL portions of a saturated aqueous sodium bicarbonate solution, and one 50 mL portion of water. The organic layer was dried with magnesium sulfate and was filtered. The filtrate was concentrated under reduced pressure to a residual oil. The oil was subjected to column chromatography on silica gel. Elution was accomplished with 1:1 ethyl acetate:heptane. The appropriate fractions were combined and concentrated under reduced pressure to yield 2.6 grams of 2-[[2-chloro-4-(3,4,5,6-tetrahydrophthalimido)phenyl]methyl]-4,4-dimethyl-3-isoxazolidinone; m.p. 102°-104° C.