Ethanol → 1H-Benzimidazole-2-acetic acid

HRID 481958Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 481958
[N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][C:2]=1CC#N.[OH-:13].[Na+].[CH2:15]([OH:17])[CH3:16]>>[N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][C:2]=1[CH2:16][C:15]([OH:13])=[O:17]

Komponenten

4

Edukt 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 204551H-Benzimidazole-2-acetonitrile

Produkt 1

HCID 261171H-Benzimidazole-2-acetic acidAusbeute 95 %

Versuchsvorschrift

A mixture of 2-benzimidazolylacetonitrile (5.58 g, 35.5 mmol) and 4M sodium hydroxide solution (25 ml) in ethanol (100 ml) was heated at reflux for 8 h. The reaction mixture was concentrated in vacuo, the residue dissolved in water (100 ml), and extracted with ethyl acetate (2×100 ml). The aqueous phase was acidified with dilute hydrochloric acid to pH 4-5, the precipitated solid was filtered, washed with water, and dried to give the title compound (5.97 g, 95%) as a buff solid; δH (DMSO-d6) 2.47 (2H, s, CH2CO2H), 7.09 (2H, m, ArH), 7.39 (1H, brs, ArH), 7.48 (1H, brs, ArH), and 12.13 (1H, brs, NH).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 8 h
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. dissolutionthe residue dissolved in water (100 ml)
  5. extractionextracted with ethyl acetate (2×100 ml)
  6. filtrationthe precipitated solid was filtered
  7. washwashed with water
  8. customdried

Quellen und Nachweise

ORD-Eintrag
ord-4053784c8cd24b068a427b1401351059
Quelldatensatz
uspto-grants-1998_08
Patentnummer
US05792768

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