O-Phenylenediamine → 1H-Benzimidazole-2-acetonitrile

HRID 565076

Reaction equation

HRID 565076 reaction equation
[C:1]1([NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH2:7].[C:9]([CH2:11][C:12](OCC)=O)#[N:10]>C(OCCC)(=O)C>[N:7]1[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=2[NH:8][C:12]=1[CH2:11][C:9]#[N:10]

Participants

4

Reactant 2

HCID 7243O-PhenylenediamineHCID 7764Ethyl cyanoacetate

Product 1

HCID 204551H-Benzimidazole-2-acetonitrile

Reagents, catalysts & solvents 1

HCID 7997Propyl AcetateSolvent

Procedure

Benzimidazole-2-acetonitrile was prepared as follows. A mixture of o-phenylenediamine (1 mole) and ethyl cyanoacetate (2 moles) was refluxed for about 30 hours, cooled, diluted with propyl acetate (225 mL), filtered, washed and dried, to provide benzimidazole-2-acetonitrile in a 60-70% yield. Benzimidazole-2-acetonitrile is also available commercially from Aldrich Chemical Company.

Workup

  1. customBenzimidazole-2-acetonitrile was prepared
  2. temperaturewas refluxed for about 30 hours
  3. temperaturecooled
  4. filtrationfiltered
  5. washwashed
  6. customdried

Sources & evidence

ORD record
ord-a970094587af454482a0d3fad6c612f0
Source dataset
uspto-grants-2001_01
Patent number
US06169185A

Linked notes

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