Benzimidazole, 2-butyl- → 2-n-Butyl-1-{(5'-chloro-2'-cyanobiphenyl-4-yl)methyl]benzimidazole

HRID 1728575Notes

Reaction equation

HRID 1728575 reaction equation
[CH2:1]([C:5]1[NH:6][C:7]2[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=2[N:9]=1)[CH2:2][CH2:3][CH3:4].[H-].[Na+].Br[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[CH:31]=[C:30]([Cl:32])[CH:29]=[CH:28][C:25]=2[C:26]#[N:27])=[CH:20][CH:19]=1>CN(C)C=O>[CH2:1]([C:5]1[N:6]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]3[CH:31]=[C:30]([Cl:32])[CH:29]=[CH:28][C:25]=3[C:26]#[N:27])=[CH:20][CH:19]=2)[C:7]2[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=2[N:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 22122Benzimidazole, 2-butyl-HCID 24758Sodium hydrideHCID 224180002-(4-Bromomethylphenyl)4-chlorobenzonitrile

Product 1

HCID 224180032-n-Butyl-1-{(5'-chloro-2'-cyanobiphenyl-4-yl)methyl]benzimidazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

522 g of 2-n-butylbenzimidazole was dissolved in 10 ml of dimethylformamide and dropwise added to 130 g of sodium hydride. The mixture was stirred at room temperature for 30 min, and 920 mg of 2-(4-bromomethylphenyl)-4-chlorobenzonitrile dissolved in 10 ml of dimethylformamide was dropwise added thereto. The mixture was stirred at room temperature for 10 min, and the reaction mixture was filtered. The filtrate was concentrated and water and ethyl acetate were added to the residue. The organic phase was separated, dried over anhydrous magnesium sulfate and then concentrated. The residue was purified by column chromatography (chloroform:ethanol=98:2) (yield: 1.12 g) .

Workup

  1. additionwas dropwise added
  2. stirringThe mixture was stirred at room temperature for 10 min
  3. filtrationthe reaction mixture was filtered
  4. concentrationThe filtrate was concentrated
  5. additionwater and ethyl acetate were added to the residue
  6. customThe organic phase was separated
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated
  9. customThe residue was purified by column chromatography (chloroform:ethanol=98:2) (yield: 1.12 g)

Sources & evidence

ORD record
ord-26b3a4271bee44c092e03c5f4b324f48
Source dataset
uspto-grants-1994_07
Patent number
US05328911

Reaction notes

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