Methyl iodide → HCID 53896831, compound

HRID 1165691Notes

Reaction equation

HRID 1165691 reaction equation
[F:1][C:2]1[CH:23]=[CH:22][CH:21]=[CH:20][C:3]=1[CH:4]=[C:5]1[NH:9][C:8](=[O:10])[N:7]([C:11]2[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:12]=2[F:18])[C:6]1=[O:19].[C:24](=O)([O-])[O-].[Cs+].[Cs+].CI>CN(C=O)C.O>[F:1][C:2]1[CH:23]=[CH:22][CH:21]=[CH:20][C:3]=1[CH:4]=[C:5]1[N:9]([CH3:24])[C:8](=[O:10])[N:7]([C:11]2[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:12]=2[F:18])[C:6]1=[O:19]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 53748986HCID 53748986, compound

Product 1

HCID 53896831HCID 53896831, compoundYield 189.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

The 5-(2-fluorobenzylidene)-3-(2,5-difluorophenyl)imidazolidine-2,4-dione (1.25 g, 3.9 mmol), cesium carbonate (0.67 g, 2.06 mmol) and methyl iodide (0.84 g, 5.9 mmol) were allowed to stir overnight in DMF (15 mL), under a N2 atmosphere. The resulting solution was 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 1.3 grams of 5-(2-fluorobenzylidene)-3-(2,5-difluorophenyl)-1-methylimidazolidine-2,4-dione m.p. 94°-97° C. (compound 106 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-5aaa8f32ed614b59ba97c34d316a19b5
Source dataset
uspto-grants-1990_03
Patent number
US04911748

Reaction notes

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