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

HRID 1730837

Reaction equation

HRID 1730837 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>[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

5

Reactant 3

HCID 111,2-DichloroethaneHCID 6491DimethylhydantoinHCID 11430Potassium Carbonate

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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 1,458 ml of dimethylformamide is reacted for 18 hours and 20 minutes at 90° C to 100° C internal temperature (external temperature 155° C), whilst constantly removing the resulting water of reaction by azeotropic circulatory distillation. Water of reaction eliminated: 110 g (94.0% of theory). Thereafter the reaction mixture, whilst still hot, is separated by filtration from the potassium chloride produced, the filtrate concentrated on a rotary evaporator at 100° C 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. customwhilst constantly removing
  3. customthe resulting water of reaction
  4. distillationby azeotropic circulatory distillation
  5. customWater of reaction
  6. customThereafter the reaction mixture, whilst still hot, is separated by filtration from the potassium chloride
  7. customproduced
  8. concentrationthe filtrate concentrated on a rotary evaporator at 100° C
  9. customthe residue is dried to constant weight at 100° C

Sources & evidence

ORD record
ord-7521e075204e4d1b9be21e562ff7b6d9
Source dataset
uspto-grants-1976_11
Patent number
US03994858

Linked notes

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