Methyl iodide → HCID 14650510, compound

HRID 1165688Notes

Reaction equation

HRID 1165688 reaction equation
[CH3:1][CH:2]([CH3:19])[CH2:3][CH:4]1[NH:8][C:7](=[O:9])[N:6]([C:10]2[CH:15]=[C:14]([F:16])[CH:13]=[CH:12][C:11]=2[F:17])[C:5]1=[O:18].[H-].[Na+].[CH3:22]I>CN(C=O)C.O>[CH3:1][CH:2]([CH3:19])[CH2:3][CH:4]1[N:8]([CH3:22])[C:7](=[O:9])[N:6]([C:10]2[CH:15]=[C:14]([F:16])[CH:13]=[CH:12][C:11]=2[F:17])[C:5]1=[O:18]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 14650506HCID 14650506, compound

Product 1

HCID 14650510HCID 14650510, compoundYield 86.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent3×

Procedure

5-(2'-Methylpropyl)-3-(2,5-difluorophenyl)imidazolidine-2,4-dione (3.0 g, 11.1 mmol) in DMF (15 mL) was added dropwise to an ice-cold suspension of sodium hydride (0.30 g, 12.5 mmol) in DMF (4 mL). The solution was allowed to stir for 2 hours, after which methyl iodide (1.04 mL, 2.38 g, 16.8 mmol) in DMF (5 mL) was added dropwise. The solution was stirred overnight and then diluted with water. The product was extracted with ethyl acetate (3×), and the combined extracts were washed with brine (saturated), dried (over MgSO4), filtered and concentrated. Purification by column chromatography gave 2.7 grams of 5-(2'-methylpropyl)-3-(2,5-difluorophenyl)-1-methylimidazolidine-2,4-dione, as an oil (compound 3 under Table A).

Workup

  1. stirringThe solution was stirred overnight
  2. extractionThe product was extracted with ethyl acetate (3×)
  3. washthe combined extracts were washed with brine (saturated)
  4. dry with materialdried (over MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by column chromatography

Sources & evidence

ORD record
ord-f3a01567152f4c7da558d87d168160fb
Source dataset
uspto-grants-1990_03
Patent number
US04911748

Reaction notes

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