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

HRID 1388906Notes

Reaction equation

HRID 1388906 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-5aaa153e88614aac9f923b89f8443bf3
Source dataset
uspto-grants-1984_02
Patent number
US04434174

Reaction notes

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