Anisole → 5-(4-Methoxyphenyl)imidazolidine-2,4-dione

HRID 1452071

Reaction equation

HRID 1452071 reaction equation
[NH:1]1[CH2:7][C:5](=[O:6])[NH:4][C:2]1=[O:3].BrBr.[C:10]1([O:16][CH3:17])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C(O)(=O)C>[CH3:17][O: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

5

Reactant 3

HCID 7519AnisoleHCID 10006HydantoinHCID 24408Bromine

Product 1

HCID 2654455-(4-Methoxyphenyl)imidazolidine-2,4-dioneYield 48%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

4.0 g (40 mmol) of hydantoin, 30 ml of acetic acid 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 2 hours. After cooling the reaction mixture to room temperature, 8.64 g (80 mmol) of anisol was added to the reaction mixture and the reaction was further conducted at a temperature of 100° C. for 6 hours. The resulting precipitate was recovered by filtration, washed with water, and then dried to obtain 3.96 g (yield 48%) of 5-(p-methoxyphenyl)hydantoin.

Workup

  1. temperatureAfter cooling the reaction mixture to room temperature
  2. waitthe reaction was further conducted at a temperature of 100° C. for 6 hours
  3. filtrationThe resulting precipitate was recovered by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-ef6827e3c6114e9099ec6e224c87bb65
Source dataset
uspto-grants-1997_02
Patent number
US05606071

Linked notes

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