N-Phenyl-o-phenylenediamine → 2-methyl-1-phenyl-1H-benzimidazole

HRID 2231239Notes

Reaction equation

HRID 2231239 reaction equation
[C:1]1([NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[NH2:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:15](C(CC)(CC)C([O-])([O-])[O-])[CH3:16]>C(O)C>[C:1]1([N:7]2[C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[N:14]=[C:15]2[CH3:16])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 68297N-Phenyl-o-phenylenediamineHCID 21875354Triethylorthoaceate

Product 1

HCID 6394272-methyl-1-phenyl-1H-benzimidazoleYield 106.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 10 g (0.054, mole) of N-phenyl-1,2phenylenediamine and 9.94 ml (0.054 mole) of triethylorthoacetate in 200 ml of ethanol was heated to reflux for 4 hours. The solvent was removed and the residue partitioned between chloroform and water. The organic layer was separated, dried and removed to give 11.99 g of product as an oil.

Workup

  1. temperatureto reflux for 4 hours
  2. customThe solvent was removed
  3. customthe residue partitioned between chloroform and water
  4. customThe organic layer was separated
  5. customdried
  6. customremoved

Sources & evidence

ORD record
ord-8c238487331849a6a131d87a5ca19e75
Source dataset
uspto-grants-1988_11
Patent number
US04782050

Reaction notes

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