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

HRID 1452063Notes

Reaction equation

HRID 1452063 reaction equation
[NH:1]1[CH2:7][C:5](=[O:6])[NH:4][C:2]1=[O:3].S(Cl)(Cl)(=O)=O.[C:13]1([OH:19])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CC(N=NC(C#N)(C)C)(C#N)C.O1CCOCC1>[OH:19][C:13]1[CH:18]=[CH:17][C:16]([CH:7]2[NH:1][C:2](=[O:3])[NH:4][C:5]2=[O:6])=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 996PhenolHCID 10006HydantoinHCID 24648Sulfuryl chloride

Product 1

HCID 942335-(4-Hydroxyphenyl)imidazolidine-2,4-dioneYield 5.3%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

4.0 g (40 mmol) of hydantoin, 50 ml of dioxane, 5.4 g (40 mmol) of sulfuryl chloride, and 0.01 g of azobisiso-butylonitrile were mixed. The reaction mixture was then stirred at a temperature of 90° C. for 5 hours. 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 80° C. for 5 hours. The resulting precipitate was recovered by filtration, washed with water, recrystallized from water and then dried to obtain 0.41 g (yield: 5.3%) of 5-(p-hydroxyphenyl)hydantoin.

Workup

  1. temperatureto cool to room temperature
  2. customreaction at a temperature of 80° C. for 5 hours
  3. filtrationThe resulting precipitate was recovered by filtration
  4. washwashed with water
  5. customrecrystallized from water
  6. customdried

Sources & evidence

ORD record
ord-fbfe2e9f1cf24e3181327bced30baccf
Source dataset
uspto-grants-1997_02
Patent number
US05606071

Reaction notes

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