Dimethylhydantoin → Hydantoin, 3-benzyl-5,5-dimethyl-

HRID 2226166Notes

Reaction equation

HRID 2226166 reaction equation
[CH3:1][C:2]1([CH3:9])[NH:6][C:5](=[O:7])[NH:4][C:3]1=[O:8].C(=O)([O-])[O-].[K+].[K+].[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CC(C)=O.C(OCC)(=O)C>[CH2:16]([N:4]1[C:3](=[O:8])[C:2]([CH3:9])([CH3:1])[NH:6][C:5]1=[O:7])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 6491DimethylhydantoinHCID 7498Benzyl BromideHCID 11430Potassium Carbonate

Product 1

HCID 141912Hydantoin, 3-benzyl-5,5-dimethyl-Yield 91.3%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To the stirred solution of 5,5-dimethylhydantoin (7 g, 54.7 mmole) in dry acetone (150 mL) under nitrogen were added potassium carbonate (10.6 g, 76.8 mmole) and benzylbromide (11.2 g, 65.9 mmole) at room temperature. The reaction mixture was refluxed for 20 hr. The reaction mixture was cooled to room temperature and the solid was filtered off by suction filtration. The titrate was concentrated on a rotary evaporator to give a residue. The residue was diluted with ethyl acetate and washed with water and brine, dried over sodium sulfate and evaporated to give 10.9 g (yield=91.3 %) of 3-benzyl-5,5-dimethylhydantoin as a white solid, mp=101°-104° C. This intermediate was subjected to the next step without further purification.

Workup

  1. temperatureThe reaction mixture was refluxed for 20 hr
  2. filtrationthe solid was filtered off by suction filtration
  3. concentrationThe titrate was concentrated on a rotary evaporator
  4. customto give a residue
  5. washwashed with water and brine
  6. dry with materialdried over sodium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-6048fe66643441ba9d8694ebe2a7efd2
Source dataset
uspto-grants-1994_09
Patent number
US05346913

Reaction notes

Loading…