HCID 10543259, compound → 4-benzyloxy-1-ethyl-2-methyl-1H-benzimidazole

HRID 2287546Notes

Reaction equation

HRID 2287546 reaction equation
[C:1]([N:4]([CH2:22][CH3:23])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:6]=1[N+:19]([O-])=O)(=O)[CH3:2]>C(O)(=O)C.C(O)C.[Fe]>[CH2:12]([O:11][C:7]1[C:6]2[N:19]=[C:1]([CH3:2])[N:4]([CH2:22][CH3:23])[C:5]=2[CH:10]=[CH:9][CH:8]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 1

HCID 10543259HCID 10543259, compound

Product 1

HCID 108017214-benzyloxy-1-ethyl-2-methyl-1H-benzimidazoleYield 34.2%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

To a solution of N-acetyl-3-benzyloxy-N-ethyl-2-nitroaniline (1.37 g) in acetic acid (11 ml) and ethanol (2.7 ml) was added iron (2.43 g), and the mixture was refluxed for 4 hours. Insoluble material was filtered off, and the filtrate was concentrated in vacuo. To the residue was added saturated sodium bicarbonate solution, and extracted with ethyl acetate. The organic layer was washed with saturated sodium bicarbonate solution, water and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by silica gel flash chromatography (hexane-ethyl acetate) to give 4-benzyloxy-1-ethyl-2-methyl-1H-benzimidazole (397 mg).

Workup

  1. temperaturethe mixture was refluxed for 4 hours
  2. filtrationInsoluble material was filtered off
  3. concentrationthe filtrate was concentrated in vacuo
  4. additionTo the residue was added saturated sodium bicarbonate solution
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with saturated sodium bicarbonate solution, water and brine
  7. dry with materialdried over magnesium sulfate
  8. customevaporated in vacuo
  9. customThe residue was purified by silica gel flash chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-f94257a0a9224cf08fe17381c8972269
Source dataset
uspto-grants-2000_07
Patent number
US06083961

Reaction notes

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