N-Phenyl-o-phenylenediamine → 1-Phenyl-1H-benzoimidazole

HRID 1471231Notes

Reaction equation

HRID 1471231 reaction equation
[C:1]1([NH:7][C:8]2[C:9]([NH2:14])=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:15](O)(=O)C.C(N)=N>COCCO>[C:1]1([N:7]2[C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[N:14]=[CH:15]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 68297N-Phenyl-o-phenylenediamineHCID 160693Formamidine acetate

Product 1

HCID 6066691-Phenyl-1H-benzoimidazole

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Procedure

To a flask were added crude N-phenylbenzene-1,2-diamine, 9.7 g formamidine acetate and 175 ml 2-methoxyethanol and the mixture was heated to reflux under nitrogen for 30 minutes. After cooling to 22 C, the solvent was removed and the mixture was dissolved in ethyl acetate and washed with water. Following removal of the solvent, the product was purified by silica gel chromatography using 50% ethyl acetate in hexane giving a tan oil.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux under nitrogen for 30 minutes
  3. temperatureAfter cooling to 22 C
  4. customthe solvent was removed
  5. dissolutionthe mixture was dissolved in ethyl acetate
  6. washwashed with water
  7. customremoval of the solvent
  8. customthe product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-9b811d6629244032ab12ab28d62fe42c
Source dataset
uspto-grants-2015_04
Patent number
US09011734B2

Reaction notes

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