4-tert-Butylphthalic anhydride → N-(4-Methoxybenzoyl)-2-(5-tert-butyl-1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)benzeneamine

HRID 395698

Reaction equation

[CH3:1][O:2][C:3]1[CH:18]=[CH:17][C:6]([C:7]([NH:9][C:10]2[C:11]([NH2:16])=[CH:12][CH:13]=[CH:14][CH:15]=2)=[O:8])=[CH:5][CH:4]=1.[C:19]([C:23]1[CH:24]=[C:25]2[C:30](=O)[O:29][C:27](=[O:28])[C:26]2=[CH:32][CH:33]=1)([CH3:22])([CH3:21])[CH3:20]>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:7]([NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[N:16]2[C:30](=[O:29])[C:25]3[C:26](=[CH:32][CH:33]=[C:23]([C:19]([CH3:21])([CH3:20])[CH3:22])[CH:24]=3)[C:27]2=[O:28])=[O:8])=[CH:17][CH:18]=1

Participants

Conditions

Temperature: 110 °C

Procedure

A slurry of N1-(4-methoxybenzoyl)-1,2-benzenediamine (100 mg, 0.413 mmol) and 4-tert-butylphthalic anhydride (84.3 mg, 0.413 mmol) in toluene (1.5 mL) was placed in a bath heated to 110° C. After 16 h, the mixture was concentrated in vacuo and the residue purified by flash chromatography (silica gel, hexanes/ethyl acetate) to afford 149 mg (85%) of the title compound. The material was further purified by recrystallization from hexanes/ethyl acetate.

Workup

concentrationthe mixture was concentrated in vacuo
customthe residue purified by flash chromatography (silica gel, hexanes/ethyl acetate)

Sources & evidence

ORD record: ord-c3af8869ce2247c6a49644eac12626b4
Source dataset: uspto-grants-2003_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06605626B2

Linked notes

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