Methyl iodide → HCID 67131041, compound

HRID 2427130Notes

Reaction equation

HRID 2427130 reaction equation
[O:1]=[C:2]1[NH:6][C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)([CH2:7][O:8][CH2:9][CH:10]=[CH2:11])[C:4](=[O:18])[N:3]1[C:19]1[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[C:21]([C:27]([F:30])([F:29])[F:28])[CH:20]=1.IC.[C:33](=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[O:1]=[C:2]1[N:6]([CH3:33])[C:5]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)([CH2:7][O:8][CH2:9][CH:10]=[CH2:11])[C:4](=[O:18])[N:3]1[C:19]1[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[C:21]([C:27]([F:30])([F:28])[F:29])[CH:20]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 67131045HCID 67131045, compound

Product 1

HCID 67131041HCID 67131041, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 0.86 g of 4-[2,5-dioxo-4-phenyl-4-[(2-propenyloxy)methyl]imidazolidin-1-yl]-2-trifluoromethyl-benzonitrile and 0.26 mL of iodomethane in 30 mL of DMF is added 430 mg of potassium carbonate. The mixture is stirred at rt for 5 hours, evaporated to dryness, diluted with water and extracted with ethyl acetate. The organic layer is dried over magnesium sulfate, filtered and evaporated. The crude product is purified by chromatography over silica gel while eluting with 70/30 heptane/ethyl acetate mixture to provide the desired product.

Workup

  1. customevaporated to dryness
  2. additiondiluted with water
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer is dried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude product is purified by chromatography over silica gel
  8. washwhile eluting with 70/30 heptane/ethyl acetate mixture

Sources & evidence

ORD record
ord-341c8ee414d24f0f89061c80f9fb9889
Source dataset
uspto-grants-2011_06
Patent number
US07968581B2

Reaction notes

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