Ethanol → 2-Benzyl-5-ethoxycarbonylbenzimidazole

HRID 1276894Notes

Reaction equation

HRID 1276894 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:12]=[CH:13][C:14]=1[NH:15][C:16](=O)[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8])([O-])=O.C(O)C>C(O)(=O)C>[CH2:17]([C:16]1[NH:1][C:4]2[CH:5]=[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH:12]=[CH:13][C:14]=2[N:15]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 702EthanolHCID 54219833Ethyl 3-nitro-4-phenylacetylaminobenzoate

Product 1

HCID 102213332-Benzyl-5-ethoxycarbonylbenzimidazoleYield 74.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 3.60 g of ethyl 3-nitro-4-phenylacetylaminobenzoate, 47 ml of ethanol, 23 ml of acetic acid and 6.4 g of reduced iron was heat-refluxed for 4 hours. The solid material was separated through filtration, and the filtrate was concentrated. To the residue were added 50 ml of ethanol and 5 g of 35% hydrochloric acid. The mixture was stirred for 40 hours while being heat-refluxed. The reaction solution was neutralized with sodium hydrogencarbonate, and was extracted with chloroform. The organic layer was concentrated under reduced pressure, and was purified through silica-gel column chromatography to give 2.30 g of 2-benzyl-5-ethoxycarbonylbenzimidazole (150).

Workup

  1. temperaturewas heat-refluxed for 4 hours
  2. customThe solid material was separated through filtration
  3. concentrationthe filtrate was concentrated
  4. additionTo the residue were added 50 ml of ethanol and 5 g of 35% hydrochloric acid
  5. temperaturewhile being heat-refluxed
  6. extractionwas extracted with chloroform
  7. concentrationThe organic layer was concentrated under reduced pressure
  8. customwas purified through silica-gel column chromatography

Sources & evidence

ORD record
ord-384b02c926f74153afdcc2a21e3277f8
Source dataset
uspto-grants-2000_12
Patent number
US06166219

Reaction notes

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