5-Nitrobenzimidazole → HCID 178439638, compound

HRID 429549Notes

Reaction equation

HRID 429549 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-1217378f342047da9dd8efe3989d6a29
Source dataset
uspto-grants-2001_11
Patent number
US06316637B1

Reaction notes

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