Propargyl bromide → 4-[2,5-Dioxo-4-(4-fluorophenyl)-4-[(2-propenyloxy)methyl]-3-(2-propynyl)imidazolidin-1-yl]-2-trifluoromethylbenzonitrile

HRID 389877Notes

Reaction equation

HRID 389877 reaction equation
[O:1]=[C:2]1[NH:6][C:5]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)([CH2:7][O:8][CH2:9][CH:10]=[CH2:11])[C:4](=[O:19])[N:3]1[C:20]1[CH:27]=[CH:26][C:23]([C:24]#[N:25])=[C:22]([C:28]([F:31])([F:30])[F:29])[CH:21]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:38](Br)[C:39]#[CH:40]>CN(C=O)C>[O:1]=[C:2]1[N:6]([CH2:40][C:39]#[CH:38])[C:5]([C:12]2[CH:13]=[CH:14][C:15]([F:18])=[CH:16][CH:17]=2)([CH2:7][O:8][CH2:9][CH:10]=[CH2:11])[C:4](=[O:19])[N:3]1[C:20]1[CH:27]=[CH:26][C:23]([C:24]#[N:25])=[C:22]([C:28]([F:30])([F:31])[F:29])[CH:21]=1

Participants

5

Reactant 3

HCID 7842Propargyl bromide2×HCID 11430Potassium CarbonateHCID 671310494-[2,5-Dioxo-4-(4-fluorophenyl)-4-[(2-propenyloxy)methyl]imidazolidin-1-yl]-2-trifluoromethylbenzonitrile

Product 1

HCID 866414594-[2,5-Dioxo-4-(4-fluorophenyl)-4-[(2-propenyloxy)methyl]-3-(2-propynyl)imidazolidin-1-yl]-2-trifluoromethylbenzonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 0.42 g of 4-[2,5-dioxo-4-(4-fluorophenyl)-4-[(2-propenyloxy)methyl]imidazolidin-1-yl]-2-trifluoromethylbenzonitrile in 3 mL of DMF, 160 mg of potassium carbonate and 0.2 mL of propargylbromide (80% solution in toluene) are added. The mixture is stirred at room temperature for 4 hours under argon atmosphere. Then 0.04 mL of propargylbromide (80% solution in toluene) is added and the mixture is stirred 1 hour at room temperature, evaporated to dryness, diluted with water and brine and extracted with ethyl acetate. The organic layer is dried over sodium sulfate filtered and evaporated.

Workup

  1. stirringthe mixture is stirred 1 hour at room temperature
  2. customevaporated to dryness
  3. additiondiluted with water and brine
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic layer is dried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-3858a7b6d6fb4454a9aff0c6846a95a9
Source dataset
uspto-grants-2013_02
Patent number
US08383608B2

Reaction notes

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