Urea → 2,2-Dimethylsuccinimide

HRID 14581Notes

Reaction equation

HRID 14581 reaction equation
[CH3:1][C:2]([CH3:10])([C:7](O)=[O:8])[CH2:3][C:4](O)=[O:5].[NH2:11]C(N)=O>O>[CH3:1][C:2]1([CH3:10])[CH2:3][C:4](=[O:5])[NH:11][C:7]1=[O:8]

Participants

4

Reactant 2

HCID 1176UreaHCID 117012,2-Dimethylsuccinic acid

Product 1

HCID 2256782,2-DimethylsuccinimideYield 89.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
160 °C

Procedure

The mixture of 10 g of 3,3-dimethylsuccinic acid and 102.7 g of urea was stirred for 10 hours at 160° C. Into the reaction mixture was added water at 100° C., and the mixture was cooled to near room temperature. The mixture was extracted with ethyl acetate three times. The organic layers were washed with a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to obtain 7.8 g of 3,3-dimethylpyrrolidin-2,5-dione.

Workup

  1. temperaturethe mixture was cooled to near room temperature
  2. extractionThe mixture was extracted with ethyl acetate three times
  3. washThe organic layers were washed with a saturated sodium chloride aqueous solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-bfec5973ad2643fa973dabb9e9e42e5e
Source dataset
uspto-grants-2010_06
Patent number
US07732448B2

Reaction notes

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