Dichloromethane → HCID 15052042, compound

HRID 329566Notes

Reaction equation

HRID 329566 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

5

Reactant 3

HCID 6344DichloromethaneHCID 124753,4,5,6-Tetrahydrophthalic anhydrideHCID 13557219HCID 13557219, compound

Product 1

HCID 15052042HCID 15052042, compoundYield 83.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

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.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for six hours
  3. customThe cooled reaction mixture
  4. washwas 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
  5. dry with materialThe organic layer was dried with magnesium sulfate
  6. filtrationwas filtered
  7. concentrationThe filtrate was concentrated under reduced pressure to a residual oil
  8. washElution
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-79c18d7348414ca7885186b65048eb54
Source dataset
uspto-grants-1990_01
Patent number
US04892578

Reaction notes

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