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

HRID 636471Notes

Reaction equation

HRID 636471 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-f1814757259c46909773cfc68000b4f6
Source dataset
uspto-grants-2001_02
Patent number
US06194396B1

Reaction notes

Loading…