Allyl bromide → (1-Allyl-4-phenyl-1H-imidazole-2-yl)(4-methylphenyl)methanone

HRID 31546

Reaktionsgleichung

Reaktionsgleichung von HRID 31546
CC(C)([O-])C.[K+].[C:7]1([C:13]2[N:14]=[CH:15][NH:16][CH:17]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH2:18](Br)[CH:19]=[CH2:20].C(N(CC)CC)C.[C:29]1([CH3:38])[CH:34]=[CH:33][C:32]([C:35](Cl)=[O:36])=[CH:31][CH:30]=1>CN(C=O)C.O>[CH2:18]([N:16]1[CH:17]=[C:13]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:14]=[C:15]1[C:35]([C:32]1[CH:33]=[CH:34][C:29]([CH3:38])=[CH:30][CH:31]=1)=[O:36])[CH:19]=[CH2:20]

Komponenten

8

Edukt 5

HCID 7841Allyl bromideHCID 8471TriethylamineHCID 134054-Methylbenzoyl ChlorideHCID 23665647Potassium tert-butoxideHCID 178418822HCID 178418822, Verbindung

Produkt 1

HCID 59863324(1-Allyl-4-phenyl-1H-imidazole-2-yl)(4-methylphenyl)methanoneAusbeute 30 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Potassium t-butoxide (2.59 g, 23.1 mmol) was dissolved in DMF (100 ml), and thereto was added 4-phenyl-1H-imidazole (3.00 g, 21 mmol) with stirring. The mixture was stirred at room temperature for 30 minutes, and thereto was added allyl bromide (3.50 g, 31.5 mmol). The mixture was stirred at 40° C. for 4 hours. To the reaction solution was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated saline, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The resulting residue was dissolved in pyridine (24 ml), and thereto were added successively triethylamine (17.9 g, 17.7 mmol) and 4-toluoyl chloride (3.7 g, 16.3 mmol), and the mixture was stirred at 60° C. for 5 hours. To the reaction solution was added water (50 ml), and the mixture was extracted with ethyl acetate. The organic layer was washed with water, 1N diluted hydrochloric acid, and saturated saline, and dried over magnesium sulfate. Then, the solvent was evaporated under reduced pressure, and the resulting residue was purified by silica gel column chromatography to give the title compound (760 mg, 30%).

Aufarbeitung

  1. stirringThe mixture was stirred at room temperature for 30 minutes
  2. stirringThe mixture was stirred at 40° C. for 4 hours
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with water and saturated saline
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was removed under reduced pressure
  7. dissolutionThe resulting residue was dissolved in pyridine (24 ml)
  8. stirringthe mixture was stirred at 60° C. for 5 hours
  9. extractionthe mixture was extracted with ethyl acetate
  10. washThe organic layer was washed with water, 1N diluted hydrochloric acid, and saturated saline
  11. dry with materialdried over magnesium sulfate
  12. customThen, the solvent was evaporated under reduced pressure
  13. customthe resulting residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-bf2eefba035149b195bd8b452f9e4bb0
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07425642B2

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