3-Bromoaniline → HCID 57516627, compound

HRID 1677552Notes

Reaction equation

HRID 1677552 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH2:8])[CH:5]=[CH:6][CH:7]=1.[CH3:9][C:10]1([CH3:17])[CH2:14][C:13](=O)[O:12][C:11]1=[O:16].C(N1C=CN=C1)(N1C=CN=C1)=O>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([N:8]2[C:13](=[O:12])[CH2:14][C:10]([CH3:17])([CH3:9])[C:11]2=[O:16])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 115623-BromoanilineHCID 682631,1'-CarbonyldiimidazoleHCID 870672,2-Dimethylsuccinic anhydride

Product 1

HCID 57516627HCID 57516627, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

3-Bromo-phenylamine (10.0 g, 58.1 mmol) and 3,3-dimethyl-dihydro-furan-2,5-dione (8.2 g, 63.9 mmol) were suspended in 387 ml of methylene chloride and heated at 50° C. for 3 hours. Carbonyldiimidazole (11.3 g, 69.7 mmol) was added in portions and the reaction was heated at 50° C. overnight. Most of the solvent was removed on a rotary evaporator. The solid residue was triturated with 20% ethyl acetate in hexanes, filtered and dried to give 15 g (92%) of somewhat impure 1-(3-bromo-phenyl)-3,3-dimethyl-pyrrolidine-2,5-dione which was used without further purification.

Workup

  1. temperaturethe reaction was heated at 50° C. overnight
  2. customMost of the solvent was removed on a rotary evaporator
  3. customThe solid residue was triturated with 20% ethyl acetate in hexanes
  4. filtrationfiltered
  5. customdried

Sources & evidence

ORD record
ord-57f060bf6bad401bb1dd0b76338e7986
Source dataset
uspto-grants-2011_08
Patent number
US08008298B2

Reaction notes

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