1,2-Dichloroethane → 3-(2-Chloroethyl)-5,5-dimethylimidazolidine-2,4-dione

HRID 2071591

Reaction equation

HRID 2071591 reaction equation
[CH3:1][C:2]1([CH3:9])[NH:6][C:5](=[O:7])[NH:4][C:3]1=[O:8].C(=O)([O-])[O-].[K+].[K+].[Cl:16][CH2:17][CH2:18]Cl.CN(C)C=O>O>[Cl:16][CH2:17][CH2:18][N:4]1[C:3](=[O:8])[C:2]([CH3:9])([CH3:1])[NH:6][C:5]1=[O:7]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 6228DimethylformamideHCID 6491DimethylhydantoinHCID 11430Potassium Carbonate

Product 1

HCID 2980853-(2-Chloroethyl)-5,5-dimethylimidazolidine-2,4-dione

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1,664 g of 5,5-dimethyl-hydantoin (13.0 mols), 897 g of anhydrous potassium carbonate (6.5 mols), 5,148 g of 1,2-dichloroethane (52 mols) and 1,485 ml of dimethylformamide is reacted for 18 hours and 20 minutes at 90° C to 100° C internal temperature (external temperature 155° C), the water of reaction produced being removed continuously by azeotropic circulatory distillation. Water of reaction split off: 110 g (94.0% of theory). Thereafter, the reaction mixture, whilst still hot, is separated by filtration from the potassium chloride produced, the filtrate is concentrated on a rotary evaporator at 100° C in a water pump vacuum and the residue is dried to constant weight at 100° C and 10-1 mm Hg.

Workup

  1. customis reacted for 18 hours and 20 minutes at 90° C to 100° C internal temperature (external temperature 155° C)
  2. customproduced
  3. custombeing removed continuously by azeotropic circulatory distillation
  4. customWater of reaction
  5. customsplit off
  6. customThereafter, the reaction mixture, whilst still hot, is separated by filtration from the potassium chloride
  7. customproduced
  8. concentrationthe filtrate is concentrated on a rotary evaporator at 100° C in a water pump vacuum
  9. customthe residue is dried to constant weight at 100° C

Sources & evidence

ORD record
ord-25d1f611cd6c4e1fa4a67558c10c97e4
Source dataset
uspto-grants-1977_09
Patent number
US04048170

Linked notes

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