Ethanol → HCID 18680954, compound

HRID 1276938Notes

Reaction equation

HRID 1276938 reaction equation
C(O)C.[N+:4]([C:7]1[CH:28]=[CH:27][C:10]([CH2:11][N:12]2[C:16]3[CH:17]=[C:18]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH:19]=[CH:20][C:15]=3[N:14]=[C:13]2[CH3:26])=[CH:9][CH:8]=1)([O-])=O>C(O)(=O)C>[NH2:4][C:7]1[CH:8]=[CH:9][C:10]([CH2:11][N:12]2[C:16]3[CH:17]=[C:18]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH:19]=[CH:20][C:15]=3[N:14]=[C:13]2[CH3:26])=[CH:27][CH:28]=1

Participants

4

Reactant 2

HCID 702EthanolHCID 18680938HCID 18680938, compound

Product 1

HCID 18680954HCID 18680954, compoundYield 100.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Six milliliters of ethanol and 0.8 ml of acetic acid were added to 0.50 g of 1-(4-nitrobenzyl)-6-ethoxycarbonyl-2-methylbenzimidazole and 0.47 g of reduced iron, and the mixture was refluxed for 4.5 hours. The reaction mixture was extracted with water and with ethyl acetate. The organic layer was washed with water, dried, and then concentrated under reduced pressure to give 0.46 g of 1-(4-aminobenzyl)-6-ethoxycarbonyl-2-methylbenzimidazole (363).

Workup

  1. temperaturethe mixture was refluxed for 4.5 hours
  2. extractionThe reaction mixture was extracted with water and with ethyl acetate
  3. washThe organic layer was washed with water
  4. customdried
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b2728ab9a3e1491eae7976d1a228ab38
Source dataset
uspto-grants-2000_12
Patent number
US06166219

Reaction notes

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