Homophthalic anhydride → HCID 15052017, compound

HRID 329562Notes

Reaction equation

HRID 329562 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:29])[O:24][C:22](=[O:23])[C:21]2=[CH:25][CH:26]=[CH:27][CH:28]=[C:20]2[CH2:19]1>O1CCCC1>[Cl:17][C:4]1[CH:3]=[C:2]([NH:1][C:18]([CH2:19][C:20]2[CH:28]=[CH:27][CH:26]=[CH:25][C:21]=2[C:22]([OH:24])=[O:23])=[O:29])[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 12801Homophthalic anhydrideHCID 13557219HCID 13557219, compound

Product 1

HCID 15052017HCID 15052017, compoundYield 58.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

This compound was prepared in a manner analogous to that of Example 1, Step C, using 4.0 grams (0.016 mole) of 2-[(4-amino-2-chlorophenyl)methyl]-4,4-dimethyl-3-isoxazolidinone and 2.6 grams (0.016 mole) of homophthalic anhydride in 150 mL of tetrahydrofuran. The reaction mixture was concentrated under reduced pressure to a residual oil. The oil was dissolved in acetone, and petroleum ether was added. The resultant solid was collected by filtration and was recrystallized from acetone/water to yield 3.9 grams of 2-[[2-chloro-4-[(2-carboxyphenylmethyl)carbonylamino]phenyl]methyl]-4,4-dimethyl-3-isoxazolidinone; m.p. 194°-196° C.

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 oil
  3. dissolutionThe oil was dissolved in acetone
  4. additionpetroleum ether was added
  5. filtrationThe resultant solid was collected by filtration
  6. customwas recrystallized from acetone/water

Sources & evidence

ORD record
ord-363e7f243a5f47ffbafbfdd32c94807e
Source dataset
uspto-grants-1990_01
Patent number
US04892578

Reaction notes

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