Phenol → 5-(4-Hydroxyphenyl)imidazolidine-2,4-dione

HRID 1452065Notes

Reaction equation

HRID 1452065 reaction equation
[NH:1]1[CH2:7][C:5](=[O:6])[NH:4][C:2]1=[O:3].BrBr.[C:10]1([OH:16])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>[Br-].[Zn+2].[Br-].O1CCOCC1>[OH:16][C:10]1[CH:15]=[CH:14][C:13]([CH:7]2[NH:1][C:2](=[O:3])[NH:4][C:5]2=[O:6])=[CH:12][CH:11]=1

Participants

6

Reactant 3

HCID 996PhenolHCID 10006HydantoinHCID 24408Bromine

Product 1

HCID 942335-(4-Hydroxyphenyl)imidazolidine-2,4-dioneYield 61%

Reagents, catalysts & solvents 2

HCID 10421208Zinc bromideCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

4.0 g (40 mmol) of hydantoin, 50 ml of dioxane, 0.025 g of zinc bromide, and 2.0 ml (40 mmol) of bromine were mixed at room temperature. The reaction mixture was then vigorously stirred at a temperature of 60° C. for 30 minutes. The reaction system was then allowed to cool to room temperature. To the reaction system was then added 7.6 g (80 mmol) of phenol. The reaction mixture was then allowed to undergo reaction at a temperature of 50° C. for 4 hours. The resulting precipitate was recovered by filtration, washed with water, and then dried to obtain 4.69 g (yield: 61%) of 5-(p-hydroxyphenyl)hydantoin.

Workup

  1. temperatureto cool to room temperature
  2. customreaction at a temperature of 50° C. for 4 hours
  3. filtrationThe resulting precipitate was recovered by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-2700260ba71142aea150353bf8b88563
Source dataset
uspto-grants-1997_02
Patent number
US05606071

Reaction notes

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