4-Bromoaniline → 1-(4-Bromophenyl)-3-phenylpyrrolidine-2,5-dione

HRID 432342Notes

Reaction equation

HRID 432342 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[C:9]1([CH:15]2[CH2:20][C:19](=O)[O:18][C:16]2=[O:17])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C1C=CC=CC=1>[Br:1][C:2]1[CH:8]=[CH:7][C:5]([N:6]2[C:19](=[O:18])[CH2:20][CH:15]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[C:16]2=[O:17])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 78074-BromoanilineHCID 136911Phenylsuccinic Anhydride

Product 1

HCID 123614511-(4-Bromophenyl)-3-phenylpyrrolidine-2,5-dioneYield 83%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 4-bromoaniline (5.48 g, 0.0318 mol) and phenylsuccinic anhydride (5.89 g, 0.0334 mol) in anhydrous benzene (80 mL) was heated at reflux for one and a half hours. The mixture was cooled to ambient temperature and concentrated under reduced pressure. To the residue, acetyl chloride (60 mL) was added and the solution was heated at reflux for one and a half hours. The reaction mixture was cooled to ambient temperature and the precipitate collected by filtration, washed with diethyl ether and dried to yield 1-(4-bromophenyl)-3-phenyl-2,5-pyrrolidinedione (8.7 g, 0.0264 mol) as an off-white solid.

Workup

  1. temperatureat reflux for one and a half hours
  2. concentrationconcentrated under reduced pressure
  3. additionTo the residue, acetyl chloride (60 mL) was added
  4. temperaturethe solution was heated
  5. temperatureat reflux for one and a half hours
  6. temperatureThe reaction mixture was cooled to ambient temperature
  7. filtrationthe precipitate collected by filtration
  8. washwashed with diethyl ether
  9. customdried

Sources & evidence

ORD record
ord-7ca01fcf3602473384502c4a04eb4517
Source dataset
uspto-grants-2003_12
Patent number
US06660744B1

Reaction notes

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