5-Nitrobenzimidazole → HCID 178441251, compound

HRID 2299122Notes

Reaction equation

HRID 2299122 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]2[N:8]=[CH:9][NH:10][C:6]=2[CH:5]=1)([O-:3])=[O:2].[Li][CH2:14][CH2:15][CH2:16][CH3:17]>CO>[CH2:14]([C:5]1[C:6]2[NH:10][CH:9]=[N:8][C:7]=2[CH:11]=[CH:12][C:4]=1[N+:1]([O-:3])=[O:2])[CH2:15][CH2:16][CH3:17].[CH2:14]([C:5]1[C:6]2[NH:10][CH:9]=[N:8][C:7]=2[CH:11]=[CH:12][C:4]=1[NH2:1])[CH2:15][CH2:16][CH3:17]

Participants

5

Reactant 2

HCID 71955-NitrobenzimidazoleHCID 178418339Butyllithium

Product 2

HCID 178441251HCID 178441251, compoundHCID 178441364HCID 178441364, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 5-nitrobenzimidazole (0.41 g, 2.5 mmol) was added a solution of n-BuLi (7.5 mmol) and reaction mixture was stirred for 1 h at 0° C. The reaction mixture was quenched by adding a few drops of H2O and concentrated in vacuo yielding an oil which was subjected to silica gel column chromatography (5% MeOH/ EtOAC) to provide 0.13 g of 4-n-butyl-5-nitrobenzimidazole and 0.19 g of 4-n-butyl-5-aminobenzimidazole. The nitrobenzimidazole was converted to the amine in hydrogenation (H2/Pd-C) to provide 0.28 g (1.5 mmol, 60%) of the desired product.

Workup

  1. customThe reaction mixture was quenched
  2. additionby adding a few drops of H2O
  3. concentrationconcentrated in vacuo
  4. customyielding an oil which

Sources & evidence

ORD record
ord-ba7ac737321842158b8688df7f6b88df
Source dataset
uspto-grants-2002_12
Patent number
US06495583B1

Reaction notes

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