Potassium Iodide → 3-(4-Methoxybenzyl)-5-methylimidazolidine-2,4-dione

HRID 2411175Notes

Reaction equation

HRID 2411175 reaction equation
[CH3:1][CH:2]1[NH:6][C:5](=[O:7])[NH:4][C:3]1=[O:8].[CH3:9][O:10][C:11]1[CH:18]=[CH:17][C:14]([CH2:15]Cl)=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>O.CN(C)C=O>[CH3:9][O:10][C:11]1[CH:18]=[CH:17][C:14]([CH2:15][N:4]2[C:3](=[O:8])[CH:2]([CH3:1])[NH:6][C:5]2=[O:7])=[CH:13][CH:12]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 692165-MethylhydantoinHCID 699934-Methyloxybenzyl chloride

Product 1

HCID 683283563-(4-Methoxybenzyl)-5-methylimidazolidine-2,4-dione

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a mixture of 5-methylimidazolidine-2,4-dione (2.00 g), 4-methoxybenzyl chloride (2.85 mL) and potassium carbonate (3.15 g) were added N,N-dimethylformamide (20 mL) and potassium iodide (0.29 g), and the mixture was stirred at 90° C. for 9 hr. The reaction mixture was cooled, water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and the solvent was evaporated. The obtained residue was recrystallized from ethyl acetate/diisopropyl ether to give the title compound (2.82 g).

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water and saturated brine
  4. customthe solvent was evaporated
  5. customThe obtained residue was recrystallized from ethyl acetate/diisopropyl ether

Sources & evidence

ORD record
ord-d0e25b499a0540669b3fa0f3f6861ba5
Source dataset
uspto-grants-2014_08
Patent number
US08816079B2

Reaction notes

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