Acetic Anhydride → 1-Acetyl-1H-pyrrole-2,5-dione

HRID 2426867Notes

Reaction equation

HRID 2426867 reaction equation
[C:1]1(=[O:7])[NH:5][C:4](=[O:6])[CH:3]=[CH:2]1.[C:8](OC(=O)C)(=[O:10])[CH3:9]>>[C:8]([N:5]1[C:4](=[O:6])[CH:3]=[CH:2][C:1]1=[O:7])(=[O:10])[CH3:9]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 10935Maleimide

Product 1

HCID 140411181-Acetyl-1H-pyrrole-2,5-dioneYield 65.8%

Procedure

A solution of maleimide (68 g; 700 mmol) in acetic anhydride (500 ml) is placed in a 1000 ml three-necked flask and the reaction mixture is then brought to reflux for 3 hours. After returning to 20° C., the reaction mixture is evaporated under reduced pressure, resulting in an oil, which is crystallized from ethyl acetate (100 ml). After filtering-off the solid and washing with ethyl acetate (25 ml) and diisopropyl ether (100 ml), and drying under reduced pressure at constant weight, N-acetylmaleimide (64.1 g; 65.8%) is isolated, the characteristics of which are as follows:

Workup

  1. temperatureto reflux for 3 hours
  2. customAfter returning to 20° C.
  3. customthe reaction mixture is evaporated under reduced pressure
  4. customresulting in an oil, which
  5. customis crystallized from ethyl acetate (100 ml)
  6. washAfter filtering-off the solid and washing with ethyl acetate (25 ml) and diisopropyl ether (100 ml)
  7. customdrying under reduced pressure at constant weight

Sources & evidence

ORD record
ord-549ade81fb894f77b4c1cb0c10b2674b
Source dataset
uspto-grants-2011_06
Patent number
US07968566B2

Reaction notes

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