Ethanol → Ethyl 1H-benzimidazole-6-carboxylate

HRID 397488

Reaktionsgleichung

Reaktionsgleichung von HRID 397488
[N:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]([OH:12])=[O:11])=[CH:9][C:4]=2[NH:3][CH:2]=1.OS(O)(=O)=O.[CH3:18][CH2:19]O>>[CH2:18]([O:11][C:10]([C:8]1[CH:7]=[CH:6][C:5]2[N:1]=[CH:2][NH:3][C:4]=2[CH:9]=1)=[O:12])[CH3:19]

Komponenten

4

Edukt 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 4594565-Benzimidazolecarboxylic acid

Produkt 1

HCID 13505555Ethyl 1H-benzimidazole-6-carboxylate

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a stirred solution of benzimidazole-5-carboxylic acid (Aldrich, 10 g, 61.7 mmol) in EtOH (200 mL) was added dropwise conc. H2SO4 (8 mL), and the solution was heated to reflux. After 1 h the solution was cooled to 60° C. and stirred for 16 h. The solution was then concentrated in vacuo and the residue was partitioned between EtOAc and saturated Na2CO3 solution. The layers were separated and the aqueous layer was extracted with EtOAc. The combined organic layers were washed with brine, dried (Na2SO4), and concentrated in vacuo to afford the title compound as a brown solid:

Aufarbeitung

  1. temperaturethe solution was heated to reflux
  2. concentrationThe solution was then concentrated in vacuo
  3. customthe residue was partitioned between EtOAc and saturated Na2CO3 solution
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted with EtOAc
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-5561ea08c67a4d34b9ede2a7dff3ea8b
Quelldatensatz
uspto-grants-2003_08
Patentnummer
US06610701B2

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