1,2-Dichloroethane → 3-(beta-Chloroethyl)-5-ethyl-5-methyl-hydantoin

HRID 2071592Notes

Reaction equation

HRID 2071592 reaction equation
[CH3:1][C:2]1([CH2:9][CH3:10])[NH:6][C:5](=[O:7])[NH:4][C:3]1=[O:8].C(=O)([O-])[O-].[K+].[K+].[Cl:17][CH2:18][CH2:19]Cl>CN(C)C=O>[Cl:17][CH2:18][CH2:19][N:4]1[C:3](=[O:8])[C:2]([CH3:1])([CH2:9][CH3:10])[NH:6][C:5]1=[O:7]

Participants

5

Reactant 3

HCID 111,2-DichloroethaneHCID 11430Potassium CarbonateHCID 821625-Ethyl-5-methylhydantoin

Product 1

HCID 214116513-(beta-Chloroethyl)-5-ethyl-5-methyl-hydantoin

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

284.3 g of 5-methyl-5-ethyl-hydantoin (2.0 mols), 138.2 g of anhydrous potassium carbonate (1.0 mol), 791.7 g of 1,2-dichloroethane (8.0 mols) and 230 ml of dimethylformamide are subjected to an azeotropic circulatory distillation, analogously to A, for 25 hours at 90° C to 107° C internal temperature (external temperature: 160° C). After completion of the reaction, the mixture is filtered whilst still hot and the filtrate is concentrated on a rotary evaporator at 90° C under a water pump vacuum. The reaction mixture is then dried to constant weight at 90° C and 10-1 mm Hg. 392.5 g of a brown, clear product (95.9% of theory) are obtained, and purified by vacuum distillation (boiling point0.2 : 147° C). Yield of pure material: 327.3 g (80% of theory). A sample recrystallised from diethyl ether melts at 58.0° C to 59.0° C.

Workup

  1. customAfter completion of the reaction
  2. filtrationthe mixture is filtered whilst still hot and the filtrate
  3. concentrationis concentrated on a rotary evaporator at 90° C under a water pump vacuum
  4. customThe reaction mixture is then dried to constant weight at 90° C
  5. custom392.5 g of a brown, clear product (95.9% of theory) are obtained
  6. distillationpurified by vacuum distillation (boiling point0.2 : 147° C)
  7. customA sample recrystallised from diethyl ether melts at 58.0° C to 59.0° C.

Sources & evidence

ORD record
ord-9d63ceace05948618b158d284b43c655
Source dataset
uspto-grants-1977_09
Patent number
US04048170

Reaction notes

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