Epichlorohydrin → N-Glycidyl-dimethylmaleimide

HRID 236912

Reaction equation

HRID 236912 reaction equation
[CH3:1][C:2]1[C:7](=[O:8])[NH:6][C:4](=[O:5])[C:3]=1[CH3:9].[K].[CH2:11]([CH:13]1[O:15][CH2:14]1)Cl>[Cl-].C[N+](C)(C)C>[CH2:11]([N:6]1[C:7](=[O:8])[C:2]([CH3:1])=[C:3]([CH3:9])[C:4]1=[O:5])[CH:13]1[O:15][CH2:14]1

Participants

4

Reactant 2

HCID 7835EpichlorohydrinHCID 70453264Potassium 2,3-dimethylmaleimide

Product 1

HCID 20479874N-Glycidyl-dimethylmaleimide

Reagents, catalysts & solvents 1

HCID 6379Tetramethylammonium chlorideCatalyst

Procedure

30 g (0.184 mol) of potassium dimethylmaleimide are suspended in 175 g (1.89 mols) of epichlorohydrin. After adding 0.05 g of tetramethylammonium chloride, the mixture is heated, whilst stirring, and boiled under reflux for 18 hours and is then filtered. After removing the unconverted chlorohydrin by distillation under a waterpump vacuum, about 30 g of a viscous, pale brown liquid which has an epoxide content of 4.9 equivalents/kg (calculated: 5.5 equivalents/kg) remain. The NMR spectrum of the product corresponds to N-glycidyl-dimethylmaleimide of the formula ##STR30##

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 18 hours
  3. filtrationis then filtered
  4. customAfter removing the unconverted chlorohydrin
  5. distillationby distillation under a waterpump vacuum, about 30 g of a viscous, pale brown liquid which

Sources & evidence

ORD record
ord-67fa3fe99a3f42b98b21201f477ecadc
Source dataset
uspto-grants-1979_06
Patent number
US04158730

Linked notes

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