1H-Benzimidazole-2-acetonitrile → HCID 828331, compound

HRID 2405027Notes

Reaction equation

HRID 2405027 reaction equation
[N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][C:2]=1[CH2:10][C:11]#[N:12].[N:13]([O-])=[O:14].[Na+]>C(O)(=O)C.O>[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10](=[N:13][OH:14])[C:11]#[N:12]

Participants

5

Reactant 2

HCID 204551H-Benzimidazole-2-acetonitrileHCID 23668193Sodium Nitrite

Product 1

HCID 828331HCID 828331, compoundYield 99.7%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To an ice-cooled stirred solution of 10 g of 2-benzimidazolylacetonitrile (63.6 mmol, 1 eq) in 50 ml of glacial acetic acid is added dropwise a solution of 4.83 g of sodium nitrite (70 mmol, 1.1 eq) dissolved in a minimum amount of water (10 mL). When the addition is completed, the reaction mixture is allowed to stir at room temperature for 1 h. The precipitate formed in the course of the reaction is filtered and washed with 2×20 ml of cold water and 2×30 ml of diethylether to provide 11.8 g of the product as light yellow solid.

Workup

  1. additionWhen the addition
  2. customThe precipitate formed in the course of the reaction
  3. filtrationis filtered
  4. washwashed with 2×20 ml of cold water and 2×30 ml of diethylether

Sources & evidence

ORD record
ord-39a1c03c11d94b96b2a2e95367c68120
Source dataset
uspto-grants-2014_08
Patent number
US08802858B2

Reaction notes

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