Ethanol → HCID 18680954, compound

HRID 276077Notes

Reaction equation

HRID 276077 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-c604464d92a5431d85ec88f09dd8a8d1
Source dataset
uspto-grants-2002_03
Patent number
US06352985B1

Reaction notes

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