Ethylene Glycol → 1-Benzyl-5-(2-hydroxyethoxy)hydantoin

HRID 1886307Notes

Reaction equation

HRID 1886307 reaction equation
C(O)(=O)C.[CH2:5]([N:12]1[CH2:18][C:16](=[O:17])[NH:15][C:13]1=[O:14])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.BrBr.[CH2:21]([OH:24])[CH2:22][OH:23]>O>[CH2:5]([N:12]1[CH:18]([O:23][CH2:22][CH2:21][OH:24])[C:16](=[O:17])[NH:15][C:13]1=[O:14])[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 176Acetic AcidHCID 24408BromineHCID 27354851-Benzylimidazolidine-2,4-dione

Product 1

HCID 198756771-Benzyl-5-(2-hydroxyethoxy)hydantoinYield 74%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

500 ml of acetic acid was added to 57 g of 1-benzylhydantoin and, while maintaining at 80° C. with stirring, 50.3 g of bromine was dropwise added thereto. After completion of the dropwise addition, the solution was further stirred for 2 hours. The reaction solution was then cooled and, while cooling with ice, 56 g of ethylene glycol was added thereto. After stirring for 30 minutes, the solution was further stirred for 3 hours at room temperature. One liter of water was added to the reaction solution, followed by extraction with 500 ml of ethyl acetate. The extract was further washed twice with 500 ml of water. The thus obtained ethyl acetate solution was dried with sodium sulfate, concentrated, and purified by silica gel chromatography to obtain 52 g of 1-benzyl-5-(2-hydroxyethoxy)hydantoin. (Yield: 74%)

Workup

  1. additionAfter completion of the dropwise addition
  2. stirringthe solution was further stirred for 2 hours
  3. temperatureThe reaction solution was then cooled
  4. additionwas added
  5. stirringAfter stirring for 30 minutes
  6. stirringthe solution was further stirred for 3 hours at room temperature
  7. extractionfollowed by extraction with 500 ml of ethyl acetate
  8. washThe extract was further washed twice with 500 ml of water
  9. dry with materialThe thus obtained ethyl acetate solution was dried with sodium sulfate
  10. concentrationconcentrated
  11. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-4e2a8d702e54478cbf7a28a47e0b6cb2
Source dataset
uspto-grants-1992_09
Patent number
US05151356

Reaction notes

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