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

HRID 904135Notes

Reaction equation

HRID 904135 reaction equation
[CH3:1][C:2]1([CH3:9])[NH:6][C:5](=[O:7])[NH:4][C:3]1=[O:8].[H-].[Na+].[H][H].[CH2:14](Cl)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CN(C)C=O>[CH2:14]([N:4]1[C:3](=[O:8])[C:2]([CH3:9])([CH3:1])[NH:6][C:5]1=[O:7])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 6491DimethylhydantoinHCID 7503Benzyl ChlorideHCID 24758Sodium hydrideHCID 178418361HCID 178418361, compound

Product 1

HCID 141912Hydantoin, 3-benzyl-5,5-dimethyl-

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

5,5-Dimethyl hydantoin (5.15 g, 0.039 mole) was added to a suspension of sodium hydride (1.87 g, 50% oil dispersion) in dry dimethylformamide (50 ml) and the mixture stirred and heated at 50° C. until evolution of hydrogen ceased. The solution was cooled and benzyl chloride (4.94 ml, 1.1 equivalents) was added and the mixture heated at 50° C. for 11/2 hours. The dimethylformamide was removed under reduced pressure and the residue partitioned between ether and brine. The ethereal extracts were combined, washed with water, dried (MgSO4) and the solvent evaporated to yield the title compound as a white crystalline solid m.p. 100°-102° C. Yield=8.0 g=91%.

Workup

  1. temperatureThe solution was cooled
  2. customThe dimethylformamide was removed under reduced pressure
  3. customthe residue partitioned between ether and brine
  4. washwashed with water
  5. dry with materialdried (MgSO4)
  6. customthe solvent evaporated

Sources & evidence

ORD record
ord-68d2a5d4c3194296b3e79ddda1996ac9
Source dataset
uspto-grants-1980_10
Patent number
US04230709

Reaction notes

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