Benzimidazole → 4-(1H-Benzimidazol-1-yl)butanenitrile

HRID 462808Notes

Reaction equation

HRID 462808 reaction equation
[N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][CH:2]=1.[H-].[Na+].Cl[CH2:13][CH2:14][CH2:15][C:16]#[N:17]>O1CCOCC1>[N:1]1([CH2:13][CH2:14][CH2:15][C:16]#[N:17])[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

5

Reactant 3

HCID 5798BenzimidazoleHCID 123364-ChlorobutyronitrileHCID 24758Sodium hydride2×

Product 1

HCID 130667534-(1H-Benzimidazol-1-yl)butanenitrile

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a suspension of 23.6 grams of benzimidazole in 300 ml of dioxane is added 9.8 grams of a 50% dispersion of sodium hydride in mineral oil and the resulting mixture is stirred at room temperature for two hours. Then a solution of 20.7 grams of 4-chlorobutyronitrile in 100 ml of dioxane is added and the mixture is refluxed for 5 hours. An additional 3 grams of sodium hydride suspension is added and the mixture refluxed for 17 hours. The mixture is then filtered, concentrated, and washed with petroleum ether to remove the mineral oil. The residual oil is then chromatographed on silica gel packed with chloroform and eluted with chloroform and chloroform containing increasing quantities of methanol. The fractions eluted with 0.5% and 1% methanol are combined and the solvent is evaporated to obtain 1H-benzimidazole-1-butanenitrile.

Workup

  1. temperaturethe mixture is refluxed for 5 hours
  2. temperaturethe mixture refluxed for 17 hours
  3. filtrationThe mixture is then filtered
  4. concentrationconcentrated
  5. washwashed with petroleum ether
  6. customto remove the mineral oil
  7. customThe residual oil is then chromatographed on silica gel
  8. washeluted with chloroform and chloroform containing
  9. temperatureincreasing quantities of methanol
  10. washThe fractions eluted with 0.5% and 1% methanol
  11. customthe solvent is evaporated

Sources & evidence

ORD record
ord-7bb4460713d84bba935fca63351b784c
Source dataset
uspto-grants-1985_05
Patent number
US04517310

Reaction notes

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