4-Bromophthalic anhydride → N-(4-Methoxybenzoyl)-2-(5-bromo-1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)benzeneamine

HRID 427549Notes

Reaction equation

HRID 427549 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.[Br:19][C:20]1[CH:21]=[C:22]2[C:27](=O)[O:26][C:24](=[O:25])[C:23]2=[CH:29][CH:30]=1>O1CCCC1>[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:27](=[O:26])[C:22]3[C:23](=[CH:29][CH:30]=[C:20]([Br:19])[CH:21]=3)[C:24]2=[O:25])=[O:8])=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 665904-Bromophthalic anhydrideHCID 785232N-(2-Aminophenyl)-4-methoxybenzamide

Product 1

HCID 18357020N-(4-Methoxybenzoyl)-2-(5-bromo-1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)benzeneamineYield 93.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
110 °C

Procedure

A pressure tube was charged with N1-(4-methoxybenzoyl)-1,2-benzenediamine (2.00 g, 8.26 mmol), 4-bromophthalic anhydride (1.88 g, 8.26 mmol), and tetrahydrofuran (8 mL). The resultant slurry was then placed in a bath heated to 110° C. for 16 h. After cooling to ambient temperature, the product was triturated with ethyl acetate/hexanes and collected by filtration. Recrystallization from ethyl acetate/hexanes yielded 3.48 g (93%) of the title compound.

Workup

  1. customThe resultant slurry was then placed in a bath
  2. temperatureAfter cooling to ambient temperature
  3. customthe product was triturated with ethyl acetate/hexanes
  4. filtrationcollected by filtration
  5. customRecrystallization from ethyl acetate/hexanes

Sources & evidence

ORD record
ord-53309fa63af242a193d60febcc4eee7d
Source dataset
uspto-grants-2001_11
Patent number
US06313122B1

Reaction notes

Loading…