Dimethylformamide → 1-(2-Bromoethyl)pyrrolidine-2,5-dione

HRID 649497Notes

Reaction equation

HRID 649497 reaction equation
[C:1]1(=[O:7])[NH:5][C:4](=[O:6])[CH2:3][CH2:2]1.CN(C)C=O.C(=O)([O-])[O-].[K+].[K+].[Br:19][CH2:20][CH2:21]Br>O>[Br:19][CH2:20][CH2:21][N:5]1[C:4](=[O:6])[CH2:3][CH2:2][C:1]1=[O:7]

Participants

6

Procedure

9.9 g of succinimide and 50 ml of N,N-dimethylformamide were put into a 200-ml three-necked flask equipped with a stirrer and a thermometer. 14 g of potassium carbonate was added to the mixture. The admixture was then stirred at room temperature for 30 minutes. 39.6 g of 1,2-dibromoethane was added to the admixture. The admixture was allowed to react at a temperature of 40° to 50° C. for 2 hours. The reaction mixture was poured into water. The aqueous mixture was then extracted with ethyl acetate. The ethyl acetate layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was crystallized with hexane. The resulting crystal was filtered off and then air-dried. Yield: 16.7 g (81%); m.p. 55° to 56° C.

Workup

  1. customequipped with a stirrer
  2. customto react at a temperature of 40° to 50° C. for 2 hours
  3. extractionThe aqueous mixture was then extracted with ethyl acetate
  4. dry with materialThe ethyl acetate layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was crystallized with hexane
  7. filtrationThe resulting crystal was filtered off
  8. customair-dried

Sources & evidence

ORD record
ord-4e584702d5f04ad395559403f6cd915c
Source dataset
uspto-grants-1988_04
Patent number
US04740455

Reaction notes

Loading…