Benzophenone → Benzimidazole

HRID 730327

Reaktionsgleichung

Reaktionsgleichung von HRID 730327
S(=O)(=O)(O)O.[NH2:6][CH2:7][C:8]#[N:9].[C:10]([C:18]1C=CC=CC=1)(=O)[C:11]1C=CC=C[CH:12]=1.[CH3:24]CN(C(C)C)C(C)C>ClCCl>[N:9]1[C:8]2[CH:18]=[CH:10][CH:11]=[CH:12][C:7]=2[NH:6][CH:24]=1

Komponenten

5

Edukt 3

HCID 3102BenzophenoneHCID 81531DiisopropylethylamineHCID 196971Aminoacetonitrile sulfate (1:1)

Produkt 1

HCID 5798BenzimidazoleAusbeute 156.273,703 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred solution of 2-aminoacetonitrile bisulfate (2.9 g, 0.013 mmol) in dichloromethane (50 mL) was added benzophenone (3.48 mL, 0.0208 mmol) followed by DIEA (4.53 mL, 0.026 mmol). After stirring 18 h, the dichloromethane solution was washed with water (50 mL), dried over sodium sulfate, filtered, and the filtrate concentrated under reduced pressure. The residue was purified on a flash silica gel column (hexanes:EtOAc, 1:1) to give 3 (2.40 g, 82%).

Aufarbeitung

  1. washthe dichloromethane solution was washed with water (50 mL)
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated under reduced pressure
  5. customThe residue was purified on a flash silica gel column (hexanes:EtOAc, 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-0e81b14c40264ccfa4abbea20ac7b045
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07582668B2

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