3a,4,5,7a-Tetrahydro-2-benzofuran-1,3-dione → N-[4-chloro-2-fluoro-5[(4,4-dimethyl-3-oxoisoxazolidin-2-yl)methyl]phenyl]-3,4,5,6-tetrahydrophthalimide

HRID 231444Notes

Reaction equation

HRID 231444 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([NH2:9])=[CH:4][C:3]=1[CH2:10][N:11]1[C:15](=[O:16])[C:14]([CH3:18])([CH3:17])[CH2:13][O:12]1.[C:19]1(=O)[O:24][C:22](=[O:23])[CH:21]2[CH2:25][CH2:26][CH:27]=[CH:28][CH:20]12>C(O)(=O)C>[Cl:1][C:2]1[C:3]([CH2:10][N:11]2[C:15](=[O:16])[C:14]([CH3:18])([CH3:17])[CH2:13][O:12]2)=[CH:4][C:5]([N:9]2[C:22](=[O:23])[C:21]3[CH2:25][CH2:26][CH2:27][CH2:28][C:20]=3[C:19]2=[O:24])=[C:6]([F:8])[CH:7]=1

Participants

4

Reactant 2

HCID 127266013a,4,5,7a-Tetrahydro-2-benzofuran-1,3-dioneHCID 20032369(2-Chloro-4-fluoro-5-aminophenyl)methyl-4,4-dimethyl-3-isoxazolidinone

Product 1

HCID 14501843N-[4-chloro-2-fluoro-5[(4,4-dimethyl-3-oxoisoxazolidin-2-yl)methyl]phenyl]-3,4,5,6-tetrahydrophthalimide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

By the method of Example 2, Step H, 3.0 g (0.011 mole) of 2-[(2-chloro-4-fluoro-5-aminophenyl)methyl-4,4-dimethyl-3-isoxazolidinone and 1.84 g (0.012 mole) of tetrahydrophthalic anhydride were reacted in 10 ml of acetic acid, yielding 3.0 g of N-[4-chloro-2-fluoro-5[(4,4-dimethyl-3-oxoisoxazolidin-2-yl)methyl]phenyl]-3,4,5,6-tetrahydrophthalimide as a yellow solid, m.p. 136°-138° C. The nmr and ir spectra were consistent with the proposed structure.

Sources & evidence

ORD record
ord-f803cbcb7d304893a5bf7982cb32472a
Source dataset
uspto-grants-1989_07
Patent number
US04846882

Reaction notes

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