Water → 1-Methyl-3-[(4-nitrophenyl)methyl]-2,4-imidazolidinedione

HRID 1398076Notes

Reaction equation

HRID 1398076 reaction equation
[CH3:1][N:2]1[CH2:8][C:6](=[O:7])[NH:5][C:3]1=[O:4].[H-].[Na+].[N+:11]([C:14]1[CH:21]=[CH:20][C:17]([CH2:18]Br)=[CH:16][CH:15]=1)([O-:13])=[O:12].O>CN(C)C=O.O1CCCC1>[CH3:1][N:2]1[CH2:8][C:6](=[O:7])[N:5]([CH2:18][C:17]2[CH:20]=[CH:21][C:14]([N+:11]([O-:13])=[O:12])=[CH:15][CH:16]=2)[C:3]1=[O:4]

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 660114-Nitrobenzyl bromideHCID 692171-Methylhydantoin

Product 1

HCID 576981821-Methyl-3-[(4-nitrophenyl)methyl]-2,4-imidazolidinedione

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture solution of 685 mg (6.0 mmol) of 1-methylhydantoin in 10 mL of N,N-dimethylformamide and 10 mL of tetrahydrofuran was added 240 mg (6.9 mmol) of sodium hydride (60% oily) at room temperature, and the mixture was stirred for 30 minutes at the same temperature. Then, 1.08 g (5.0 mmol) of p-nitrobenzyl bromide was added to the reaction mixture, and the mixture was stirred for over night at room temperature. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was dried over with anhydrous sodium sulfate and the solvent was removed under reduced pressure to give 1.38 g (quantitative) of the title compound.

Workup

  1. stirringthe mixture was stirred for over night at room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialThe organic layer was dried over with anhydrous sodium sulfate
  4. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-2d58e319cb3d4a74aef241d3813e263f
Source dataset
uspto-grants-2014_12
Patent number
US08901315B2

Reaction notes

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