Urea → 2,2-Dimethylsuccinimide

HRID 423166Notes

Reaction equation

HRID 423166 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

10 g of 3,3-dimethyl succinic acid and 102.7 g of urea were mixed and stirred at 160° C. for 10 hours. Then water was added to the reaction mixture which was cooled to about 100° C., and further cooled to about room temperature, then extracted with ethyl acetated three times. The organic layers were joined, washed with saturated aqueous solution of sodium chloride, dried with anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography to obtain 7.8 g of 3,3-dimethyl-2,5-pyrrolidine dion.

Workup

  1. temperaturewas cooled to about 100° C.
  2. temperaturefurther cooled to about room temperature
  3. extractionextracted with ethyl
  4. washwashed with saturated aqueous solution of sodium chloride
  5. dry with materialdried with anhydrous magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-afc57db5b74d4b78be92e6daa89e28b4
Source dataset
uspto-grants-2012_01
Patent number
US08101753B2

Reaction notes

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