Methyl iodide → 4-[2,5-Dioxo-4-(4-fluorophenyl)-3-methyl-4-[(2-propenyloxy)methyl]imidazolidin-1-yl]-2-trifluoromethylbenzonitrile

HRID 389875Notes

Reaction equation

HRID 389875 reaction equation
[C:1](=O)([O-])[O-].[K+].[K+].IC.[O:9]=[C:10]1[NH:14][C:13]([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)([CH2:15][O:16][CH2:17][CH:18]=[CH2:19])[C:12](=[O:27])[N:11]1[C:28]1[CH:35]=[CH:34][C:31]([C:32]#[N:33])=[C:30]([C:36]([F:39])([F:38])[F:37])[CH:29]=1>CN(C=O)C>[O:9]=[C:10]1[N:14]([CH3:1])[C:13]([C:20]2[CH:21]=[CH:22][C:23]([F:26])=[CH:24][CH:25]=2)([CH2:15][O:16][CH2:17][CH:18]=[CH2:19])[C:12](=[O:27])[N:11]1[C:28]1[CH:35]=[CH:34][C:31]([C:32]#[N:33])=[C:30]([C:36]([F:38])([F:39])[F:37])[CH:29]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 671310494-[2,5-Dioxo-4-(4-fluorophenyl)-4-[(2-propenyloxy)methyl]imidazolidin-1-yl]-2-trifluoromethylbenzonitrile

Product 1

HCID 671309984-[2,5-Dioxo-4-(4-fluorophenyl)-3-methyl-4-[(2-propenyloxy)methyl]imidazolidin-1-yl]-2-trifluoromethylbenzonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

325 mg of potassium carbonate and 0.25 mL of iodomethane are added to a solution of 0.85 g of 4-[2,5-dioxo-4-(4-fluorophenyl)-4-[(2-propenyloxy)methyl]imidazolidin-1-yl]-2-trifluoromethylbenzonitrile obtained in step 4, dissolved in 3 mL of DMF. The mixture is stirred at rt for 4 hours under argon atmosphere, evaporated to dryness, diluted with water and brine and extracted with ethyl acetate. The organic layer is dried over sodium sulfate, filtered and evaporated to provide the desired product.

Workup

  1. customevaporated to dryness
  2. additiondiluted with water and brine
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer is dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-bde40fa0fff64822b1fd5f21daa777c8
Source dataset
uspto-grants-2013_02
Patent number
US08383608B2

Reaction notes

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