Phthalic Anhydride → HCID 15051990, compound

HRID 329561Notes

Reaction equation

HRID 329561 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:28])[O:23][C:21](=[O:22])[C:20]2=[CH:24][CH:25]=[CH:26][CH:27]=[C:19]12>O1CCCC1.C(Cl)Cl>[Cl:17][C:4]1[CH:3]=[C:2]([NH:1][C:18]([C:19]2[CH:27]=[CH:26][CH:25]=[CH:24][C:20]=2[C:21]([OH:23])=[O:22])=[O:28])[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 2

HCID 6811Phthalic AnhydrideHCID 13557219HCID 13557219, compound

Product 1

HCID 15051990HCID 15051990, compoundYield 10.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

This compound was prepared in a manner analogous to that of Example 1, Step C, using 3.0 grams (0.012 mole) of 2-[(4-amino-2-chlorophenyl)methyl]-4,4-dimethyl-3-isoxazolidinone and 1.8 grams (0.012 mole) of phthalic anhydride in 125 mL of tetrahydrofuran. The reaction mixture was dissolved in 200 mL of methylene chloride and washed with four 50 mL portions of an aqueous 10% hydrochloric acid solution. The organic layer was dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to a semi-solid residue. The residue was stirred and heated in ethyl acetate-heptane. The resultant solid was collected by filtration and was recrystallized from acetate/hexane to yield 0.5 gram of 2-[[2-chloro-4-[(2-carboxyphenyl)carbonylamino]phenyl]methyl]-4,4-dimethyl-3-isoxazolidinone; m.p. 172° C., dec.

Workup

  1. customThis compound was prepared in a manner analogous to that of Example 1, Step C
  2. washwashed with four 50 mL portions of an aqueous 10% hydrochloric acid solution
  3. dry with materialThe organic layer was dried with magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure to a semi-solid residue
  6. temperatureheated in ethyl acetate-heptane
  7. filtrationThe resultant solid was collected by filtration
  8. customwas recrystallized from acetate/hexane

Sources & evidence

ORD record
ord-7ec9cc5dff5e45279abfbbfd8e6a7dcd
Source dataset
uspto-grants-1990_01
Patent number
US04892578

Reaction notes

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