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

HRID 2427138Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2427138
[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

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-52f50dd7c7ce4add8150c89b79256c0d
Quelldatensatz
uspto-grants-2011_06
Patentnummer
US07968581B2

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