Benzimidazole → 3-(1H-benzimidazol-1-yl)propanenitrile

HRID 1902449Notes

Reaction equation

HRID 1902449 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.[C:10](#[N:13])[CH:11]=[CH2:12].[OH-].C([N+](C)(C)C)C1C=CC=CC=1>O1CCOCC1>[N:1]1([CH2:12][CH2:11][C:10]#[N:13])[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 7855AcrylonitrileHCID 66854Benzyltrimethylammonium hydroxide

Product 1

HCID 29985553-(1H-benzimidazol-1-yl)propanenitrile

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 15.8 grams of 1H-benzimidazole, 8 grams of acrylonitrile and 0.2 ml of benzyltrimethylammonium hydroxide (40% solution in methanol) in 200 ml of dioxane was stirred at room temperature for 24 hours. The solvent was evaporated from the resulting yellow solution under reduced pressure and the residual yellow solid was triturated first with ether and then with water to give 1H-benzimidazole-1-propionitrile melting at about 108°-110° C.

Workup

  1. customThe solvent was evaporated from the resulting yellow solution under reduced pressure
  2. customthe residual yellow solid was triturated first with ether

Sources & evidence

ORD record
ord-1b72e175346c4c3283b4e744a1a46f48
Source dataset
uspto-grants-1982_12
Patent number
US04363808

Reaction notes

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