5-Nitrobenzimidazole → HCID 178439638, compound

HRID 2299121Notes

Reaction equation

HRID 2299121 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].[CH2:13]([Mg]Br)[CH2:14][CH3:15].ClC1C(=O)C(Cl)=C(Cl)C(=O)C=1Cl>C1COCC1>[CH2:13]([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])[CH2:14][CH3:15]

Participants

5

Reactant 3

HCID 71955-NitrobenzimidazoleHCID 8371ChloranilHCID 178455851HCID 178455851, compound

Product 1

HCID 178439638HCID 178439638, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-15 °C

Procedure

To a solution of 5-nitrobenzimidazole (2.3 g, 14 mmol) was added 14 ml of n-PrMgBr solution (42 mmol) and reaction mixture was stirred for 2 h at −15° C. The reaction was quenched by adding a solution of tetrachloro-1,4-benzoquinone (4 g, 16 mmol) in 10 ml of THF. The reaction mixture was concentrated in vacuo to provide an oil, which was subjected to column chromatographic separation (EtOAc, neat) to provide 1.4 g (7.2 mmol, 52%) of 4-n-propyl-5-nitrobenzimidazole, which was converted to the corresponding amine (1.2 g, >95%) by hydrogenation(H2, Pd/C).

Workup

  1. customThe reaction was quenched
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customto provide an oil, which
  4. customwas subjected to column chromatographic separation (EtOAc, neat)

Sources & evidence

ORD record
ord-6be41e55978b44d681e29ed804fc7403
Source dataset
uspto-grants-2002_12
Patent number
US06495583B1

Reaction notes

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