Acetic Acid → 1-Benzyl-5-hydroxyimidazolidine-2,4-dione

HRID 324906Notes

Reaction equation

HRID 324906 reaction equation
C(O)(=[O:3])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.C(=O)(O)[O-].[Na+]>O.C(OCC)(=O)C>[OH:3][CH:18]1[N:12]([CH2:5][C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:13](=[O:14])[NH:15][C:16]1=[O:17]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 24408BromineHCID 516892Sodium BicarbonateHCID 27354851-Benzylimidazolidine-2,4-dione

Product 1

HCID 101304681-Benzyl-5-hydroxyimidazolidine-2,4-dione

Reagents, catalysts & solvents 2

HCID 962WaterSolvent3×HCID 8857Ethyl AcetateSolvent

Procedure

In a solvent mixture of 250 ml of acetic acid and 40 ml of ethyl acetate was dispersed 190 g of 1-benzylhydantoin and the mixture was refluxed under heating with stirring. To the mixture was added dropwise 164 g of bromine over a period of one hour, and the mixture was refluxed under heating for 30 minutes. The solvent was distilled off under a reduced pressure and the residue was allowed to stand for cooling. To the residue were added dropwise an aqueous sodium bicarbonate solution prepared by dissolving 53 g of sodium bicarbonate in 400 ml of water and then 200 ml of water. The reaction vessel was cooled with water and the crystals thus-deposited were collected by filtration, washed with water and dried to obtain 182 g of 5-hydroxy-1-benzylhydantoin as colorless crystals.

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating
  3. temperaturethe mixture was refluxed
  4. temperatureunder heating for 30 minutes
  5. distillationThe solvent was distilled off under a reduced pressure
  6. temperaturefor cooling
  7. additionTo the residue were added dropwise an aqueous sodium bicarbonate solution
  8. customprepared
  9. filtrationthe crystals thus-deposited were collected by filtration
  10. washwashed with water
  11. customdried

Sources & evidence

ORD record
ord-17dd8c638def47cd8913f7e54029a4a9
Source dataset
uspto-grants-2001_04
Patent number
US06220925B1

Reaction notes

Loading…