Methyl iodide → HCID 57032911, compound

HRID 1165695Notes

Reaction equation

HRID 1165695 reaction equation
[CH:1]1([CH:7]=[C:8]2[NH:12][C:11](=[O:13])[N:10]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[F:20])[C:9]2=[O:21])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:22](=O)([O-])[O-].[Cs+].[Cs+].CI>CN(C=O)C.O>[CH:1]1([CH:7]=[C:8]2[N:12]([CH3:22])[C:11](=[O:13])[N:10]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[F:20])[C:9]2=[O:21])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 57222144HCID 57222144, compound

Product 1

HCID 57032911HCID 57032911, compoundYield 80.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

The 5-cyclohexylmethylene-3-(2-fluorophenyl)-imidazolidine-2,4-dione (2.25 g, 7.81 mmol), cesium carbonate (2.6 g, 8.0 mmol) and methyl iodide (1.66 g, 11.7 mmol) were stirred overnight in DMF (25 mL). The solution was diluted with water and extracted with ethyl acetate (3×). The combined extracts were washed with brine (saturated, 2×), dried (over MgSO4), filtered and concentrated. Purification by column chromatography afforded 1.9 grams of 5-cyclohexylmethylene-3-(2-fluorophenyl)-1-methylimidazolidine-2,4-dione, a white solid, m.p. 131°-137° C.

Workup

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

Sources & evidence

ORD record
ord-c75575912c544a619ddd028dd4ff9cfe
Source dataset
uspto-grants-1990_03
Patent number
US04911748

Reaction notes

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