Methyl iodide → 5-Benzyl-3-(2,5-difluorophenyl)-1-methylimidazolidine-2,4-dione

HRID 1165687Notes

Reaction equation

HRID 1165687 reaction equation
[CH2:1]([CH:8]1[NH:12][C:11](=[O:13])[N:10]([C:14]2[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=2[F:21])[C:9]1=[O:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH3:25]I>CN(C=O)C.O>[CH2:1]([CH:8]1[N:12]([CH3:25])[C:11](=[O:13])[N:10]([C:14]2[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=2[F:21])[C:9]1=[O:22])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 146505055-Benzyl-3-(2,5-difluorophenyl)imidazolidine-2,4-dione

Product 1

HCID 146505095-Benzyl-3-(2,5-difluorophenyl)-1-methylimidazolidine-2,4-dioneYield 56.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

5-Benzyl-3-(2,5-difluorophenyl)imidazolidine-2,4-dione (2.0 g, 6.62 mmol) in DMF (10 mL) was added dropwise to a suspension of sodium hydride (166 mg, 6.95 mmol) in DMF (5 mL) at 0° C. The solution was stirred for 1 hour; then methyl iodide (0.62 mL, 9.9 mmol) was added and the mixture was stirred for 5 hours, then diluted with water and extracted with ethyl acetate (3×). The combined extracts were washed with brine (saturated), dried (over MgSO4), filtered and concentrated to give 1.19 grams of 5-benzyl-3-(2,5-difluorophenyl)-1-methylimidazolidine-2,4-dione, as an oil (compound 1 under Table A).

Workup

  1. stirringthe mixture was stirred for 5 hours
  2. extractionextracted with ethyl acetate (3×)
  3. washThe combined extracts were washed with brine (saturated)
  4. dry with materialdried (over MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d2a4a2b10bf94d08bf52d5ddaab297c9
Source dataset
uspto-grants-1990_03
Patent number
US04911748

Reaction notes

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