Benzyl Chloride → 1-Benzyl-2-pyridin-2-yl-1H-benzoimidazole

HRID 1926471

Reaktionsgleichung

Reaktionsgleichung von HRID 1926471
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[NH:8][C:9]2[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=2[N:11]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:22](Cl)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CN(C)C=O>[CH2:22]([N:11]1[C:10]2[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=2[N:8]=[C:7]1[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Komponenten

5

Edukt 3

HCID 7503Benzyl Chloride2×HCID 11430Potassium CarbonateHCID 708212-(2'-Pyridyl)benzimidazole

Produkt 1

HCID 7973371-Benzyl-2-pyridin-2-yl-1H-benzoimidazoleAusbeute 82,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a flask were added 2.0 g 2-(2-pyridyl)benzimidazole, 1.8 g potassium carbonate, 30 ml N,N-dimethylformamide and the mixture was stirred under nitrogen at 10 C. 1.5 g benzyl chloride were added and the mixture allowed to warm to 22 C and stirred for 3 hours. Another 0.3 g benzyl chloride was added and the reaction was stirred at 22 C for another 16 hours. The reaction was quenched with 40 ml water and the product was filtered and washed with water. The product was dissolved in 10 ml ethanol and 15 ml of water were added. After cooling to 5 C, the product was filtered, washed and dried resulting in 2.4 g of off-white solid.

Aufarbeitung

  1. temperatureto warm to 22 C
  2. stirringstirred for 3 hours
  3. stirringthe reaction was stirred at 22 C for another 16 hours
  4. customThe reaction was quenched with 40 ml water
  5. filtrationthe product was filtered
  6. washwashed with water
  7. dissolutionThe product was dissolved in 10 ml ethanol
  8. addition15 ml of water were added
  9. temperatureAfter cooling to 5 C
  10. filtrationthe product was filtered
  11. washwashed
  12. customdried

Quellen und Nachweise

ORD-Eintrag
ord-5442a9017f33442f8e703cb55ca08d30
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08182718B2

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