Benzimidazole → 1-propyl-1h-benzimidazole

HRID 1926487Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1926487
[N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].I[CH2:17][CH2:18][CH3:19]>CN(C)C=O>[CH2:17]([N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1)[CH2:18][CH3:19]

Komponenten

5

Edukt 3

HCID 5798BenzimidazoleHCID 11430Potassium CarbonateHCID 336431-Iodopropane

Produkt 1

HCID 7387691-propyl-1h-benzimidazoleAusbeute 55,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a flask were added 2.0 g benzimidazole, 3.5 g potassium carbonate, 4.3 g 1-iodopropane and 20 ml N,N-dimethylformamide. The mixture was heated to 45 C under nitrogen for 16 hours and then quenched with 30 ml water and the product was extracted with ethyl acetate. Following removal of the solvent, the product was purified by silica gel chromatography using 66% ethyl acetate in hexane. The brown oil was again purified by silica gel chromatography using ethyl acetate, giving a slightly yellow oil 1.5 g.

Aufarbeitung

  1. temperatureThe mixture was heated to 45 C under nitrogen for 16 hours
  2. customquenched with 30 ml water
  3. extractionthe product was extracted with ethyl acetate
  4. customremoval of the solvent
  5. customthe product was purified by silica gel chromatography
  6. customThe brown oil was again purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-7deddd5e5917413291d9d7ca9540347b
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08182718B2

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