Phthalic Anhydride → HCID 15051991, compound

HRID 329569Notes

Reaction equation

HRID 329569 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]([Br: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>[Br: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

4

Reactant 2

HCID 6811Phthalic AnhydrideHCID 14550851HCID 14550851, compound

Product 1

HCID 15051991HCID 15051991, compoundYield 93.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

This compound was prepared in a manner analogous to that of Example 1, Step C, using 2.0 grams (0.0067 mole) of 2-[(4-amino-2-bromophenyl)methyl]-4,4-dimethyl-3-isoxazolidinone and 1.0 gram (0.0067 mole) of phthalic anhydride in 50 ml of tetrahydrofuran. The reaction mixture was concentrated under reduced pressure to a residual solid. The solid was recrystallized from ethyl acetate-hexane to yield 2.8 grams of 2-[[2-bromo-4-[(2-carboxyphenyl)carbonylamino]phenyl]methyl]-4,4-dimethyl-3-isoxazolidinone, m.p. 177° C., dec.

Workup

  1. customThis compound was prepared in a manner analogous to that of Example 1, Step C
  2. concentrationThe reaction mixture was concentrated under reduced pressure to a residual solid
  3. customThe solid was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-9ad1fa9b11b5463faceac04003d4414d
Source dataset
uspto-grants-1990_01
Patent number
US04892578

Reaction notes

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