Phenol → 5-(4-Hydroxyphenyl)imidazolidine-2,4-dione
Reaction equation
Cl[CH:2]1[NH:6][C:5](=[O:7])[NH:4][C:3]1=[O:8].[C:9]1([OH:15])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>O1CCOCC1>[OH:15][C:9]1[CH:14]=[CH:13][C:12]([CH:2]2[NH:6][C:5](=[O:7])[NH:4][C:3]2=[O:8])=[CH:11][CH:10]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
1.34 g (10 mmol) of 5-chlorohydantoin and 1.88 g (20 mmol) of phenol were dissolved in 10 ml of dioxane. The solution was then heated to a temperature of 70° C. with stirring for 6 hours. The reaction system was then allowed to cool to room temperature. The reaction system 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 0.93 g (4.8 mmol; yield: 48%) of 5-(p-hydroxyphenyl)hydantoin in the form of white crystal. The crystal thus obtained exhibited a melting point of 262° to 264°0 C. (decomposition). The IR spectrum, NMR spectrum, and Rf value of thin layer chromatography showed a good conformance to that of a specimen which had been separately synthesized.
Workup
- temperatureto cool to room temperature
- temperatureThe reaction system was further cooled over an ice bath for 2 hours
- filtrationThe resulting crystal was recovered by filtration
- washwashed thoroughly with water
- customair-dried
Sources & evidence
- ORD record
- ord-bf77d185fabb4e66bf342785a0fde407
- Source dataset
- uspto-grants-1997_02
- Patent number
- US05606071
Reaction notes
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