Dimethylhydantoin → 3-(4-Chlorobutyl)-5,5-dimethyl-hydantoin

HRID 1730838Notes

Reaction equation

HRID 1730838 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][CH2:19][CH2:20]Cl>>[Cl:16][CH2:17][CH2:18][CH2:19][CH2:20][N:4]1[C:3](=[O:8])[C:2]([CH3:9])([CH3:1])[NH:6][C:5]1=[O:7]

Participants

4

Reactant 3

HCID 6491DimethylhydantoinHCID 80591,4-DichlorobutaneHCID 11430Potassium Carbonate

Product 1

HCID 138858453-(4-Chlorobutyl)-5,5-dimethyl-hydantoin

Procedure

A mixture of 538 g of 5,5-dimethyl-hydantoin (4.2 mols), 290 g of anhydrous potassium carbonate (2.1 mols) and 2,130 g of 1,4-dichlorobutane (16.77 mols) is reacted for 8 hours at 138° to 141° C internal temperature (external temperature 200° C), as described under Example 1 (a). Working up is carried out according to Example 1 (a), and 830.9 g of a brown, viscous crude product (90.5% of theory) are obtained, and are purified by vacuum distillation (boiling point0.2 : 151°-153° C) and subsequent recrystallisation from diethyl ether. The pure product melts at 54.4° to 56.3° C.

Workup

  1. customis reacted for 8 hours at 138° to 141° C internal temperature (external temperature 200° C)
  2. customare obtained
  3. distillationare purified by vacuum distillation (boiling point0.2 : 151°-153° C) and subsequent recrystallisation from diethyl ether

Sources & evidence

ORD record
ord-4c67a6a63aa84c9fb10fc0ed6149c7ab
Source dataset
uspto-grants-1976_11
Patent number
US03994858

Reaction notes

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