Hydantoin → 3-(4-Nitrobenzyl)imidazolidine-2,4-dione

HRID 483373Notes

Reaction equation

HRID 483373 reaction equation
[NH:1]1[CH2:7][C:5](=[O:6])[NH:4][C:2]1=[O:3].[OH-].[Na+].[N+:10]([C:13]1[CH:20]=[CH:19][C:16]([CH2:17]Br)=[CH:15][CH:14]=1)([O-:12])=[O:11]>CO>[N+:10]([C:13]1[CH:20]=[CH:19][C:16]([CH2:17][N:4]2[C:5](=[O:6])[CH2:7][NH:1][C:2]2=[O:3])=[CH:15][CH:14]=1)([O-:12])=[O:11]

Participants

5

Reactant 3

HCID 10006HydantoinHCID 14798Sodium HydroxideHCID 660114-Nitrobenzyl bromide

Product 1

HCID 107522073-(4-Nitrobenzyl)imidazolidine-2,4-dioneYield 57.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of hydantoin (5.0 g, Aldrich) in 2N aqu. NaOH (25 ml) was stirred at room temperature for 1 hour, then a solution of p-nitrobenzyl bromide (10.8 g, Aldrich) in methanol (50 ml) was added and the mixture refluxed for 16 hours. The mixture was cooled and the pale yellow precipitate filtered off, dried in vacuo, and recrystalised from ethanol to give the desired product as pale yellow crystals (6.8 g).

Workup

  1. temperaturethe mixture refluxed for 16 hours
  2. temperatureThe mixture was cooled
  3. filtrationthe pale yellow precipitate filtered off
  4. customdried in vacuo
  5. customrecrystalised from ethanol

Sources & evidence

ORD record
ord-86d2fe63c1234c87a9d1b4441aa934dc
Source dataset
uspto-grants-1993_07
Patent number
US05225431

Reaction notes

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