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

HRID 1165693Notes

Reaction equation

HRID 1165693 reaction equation
[CH3:1][C:2]1[CH:23]=[CH:22][C:5]([CH:6]=[C:7]2[NH:11][C:10](=[O:12])[N:9]([C:13]3[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=3[F:20])[C:8]2=[O:21])=[CH:4][CH:3]=1.[C:24](=O)([O-])[O-].[Cs+].[Cs+].CI>CN(C=O)C.O>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([CH:6]=[C:7]2[N:11]([CH3:24])[C:10](=[O:12])[N:9]([C:13]3[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=3[F:20])[C:8]2=[O:21])=[CH:22][CH:23]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 54007378HCID 54007378, compound

Product 1

HCID 537367675-(4-Methylbenzylidene)-3-(2,5-difluorophenyl)-1-methylimidazolidine-2,4-dioneYield 186.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

The 5-(4-methylbenzylidene)-3-(2,5-difluorophenyl)imidazolidine-2,4-dione (2.25 g, 7.16 mmol), cesium carbonate (1.22 g, 3.76 mmol) and methyl iodide (1.5 g, 3.76 mmol) were stirred together in DMF (20 mL) overnight. The solution was 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 2.3 grams of 5-(4-methylbenzylidene)-3-(2,5-difluorophenyl)-1-methylimidazolidine-2,4-dione, m.p. 136°-140° C. (compound 104 under Table B).

Workup

  1. extractionextracted with ethyl acetate (3×)
  2. washThe combined extracts were washed with brine (saturated)
  3. dry with materialdried (over MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-1d0f4f3c74cb40cd8079abffbee4e705
Source dataset
uspto-grants-1990_03
Patent number
US04911748

Reaction notes

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