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

HRID 1452066Notes

Reaction equation

HRID 1452066 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>CS(O)(=O)=O.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 24408Bromine2×

Product 1

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

Reagents, catalysts & solvents 2

HCID 6395Methanesulfonic AcidCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4.00 g (40 mmol) of hydantoin, 6.4 g (40 mmol) of bromine, 0.01 g of methanesulfonic acid, and 30 ml of dioxane was heated to a temperature of 100° C. with stirring for 3 minutes. The reaction mixture was further stirred at a temperature of 50° C. until bromine disappeared. To the reaction mixture was then added 7.52 g (80 mmol) of phenol. The reaction mixture was then heated to a temperature of 50° C. with stirring for 4 hours. The reaction mixture was then allowed to cool to room temperature. The reaction mixture was further cooled over an ice bath for 2 hours. The resulting crystal was recovered by filtration, washed thoroughly with water, and then air-dried to obtain 4.69 g (24.4 mmol; yield: 61%) of 5-(p-hydroxyphenyl)-hydantoin in the form of white crystal.

Workup

  1. temperatureThe reaction mixture was then heated to a temperature of 50° C.
  2. stirringwith stirring for 4 hours
  3. temperatureto cool to room temperature
  4. temperatureThe reaction mixture was further cooled over an ice bath for 2 hours
  5. filtrationThe resulting crystal was recovered by filtration
  6. washwashed thoroughly with water
  7. customair-dried

Sources & evidence

ORD record
ord-0214e8f2588846e4b8c5dcb704537440
Source dataset
uspto-grants-1997_02
Patent number
US05606071

Reaction notes

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