Ethanol → 2-Benzyl-5-ethoxycarbonylbenzimidazole

HRID 321964Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 321964
[N+:1]([C:4]1[C:5](CC)=[C:6]([CH:10]=[CH:11][C:12]=1[NH:13][C:14](=O)[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:7]([O-:9])=[O:8])([O-])=O.[CH2:25](O)[CH3:26]>C(O)(=O)C>[CH2:15]([C:14]1[NH:1][C:4]2[CH:5]=[C:6]([C:7]([O:9][CH2:25][CH3:26])=[O:8])[CH:10]=[CH:11][C:12]=2[N:13]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Komponenten

4

Edukt 2

HCID 702EthanolHCID 701409133-Nitro-4-phenylacetylamino-ethylbenzoate

Produkt 1

HCID 102213332-Benzyl-5-ethoxycarbonylbenzimidazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

A mixture of 3-nitro-4-phenylacetylamino-ethylbenzoate (3.60 g), ethanol (47 ml), acetic acid (23 ml) and reduced iron (6.4 g) is refluxed for four hours. Solids are separated through filtration and the filtrate is concentrated. Ethanol (50 ml) and 35% hydrochloric acid (5 g) are added to the residue and the solution is refluxed for 40 hours. The solution is neutralized with sodium bicarbonate and chloroform extraction is performed. The organic layer is concentrated under reduced pressure and then purified using silica gel column chromatography. Thus, 2-benzyl-5-ethoxycarbonylbenzimidazole (2.30 g) is obtained. 1H-NMR (CDCl3, δ): 1.39 (3H, t, J=7.1 Hz), 4.26 (2H, s), 4.37 (2H, q, J=7.1 Hz), 7.22-7.36 (5H, m), 7.50 (1H, d, J=8.6 Hz), 7.94 (1H, dd, J=1.5 and 8.6 Hz), 8.23 (1H, d, J=1.3 Hz).

Aufarbeitung

  1. temperatureis refluxed for four hours
  2. customSolids are separated through filtration
  3. concentrationthe filtrate is concentrated
  4. additionEthanol (50 ml) and 35% hydrochloric acid (5 g) are added to the residue
  5. temperaturethe solution is refluxed for 40 hours
  6. extractionThe solution is neutralized with sodium bicarbonate and chloroform extraction
  7. concentrationThe organic layer is concentrated under reduced pressure
  8. custompurified

Quellen und Nachweise

ORD-Eintrag
ord-272485b9e0474238a166b526b3f48b61
Quelldatensatz
uspto-grants-2001_04
Patentnummer
US06211177B1

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