O-Phenylenediamine → 2-(4-Bromophenyl)benzimidazole

HRID 375541Notes

Reaction equation

HRID 375541 reaction equation
S(=O)(O)[O-].[Na+].[Br:6][C:7]1[CH:14]=[CH:13][C:10]([CH:11]=O)=[CH:9][CH:8]=1.[NH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[NH2:22]>C(O)C>[Br:6][C:7]1[CH:14]=[CH:13][C:10]([C:11]2[NH:22][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=3[N:15]=2)=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 7243O-PhenylenediamineHCID 707414-BromobenzaldehydeHCID 23665763Sodium Bisulfite

Product 1

HCID 2861822-(4-Bromophenyl)benzimidazoleYield 71.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium bisulfite (14.4 g) is added to 4-bromobenzaldehye (17.1 g) in ethanol (100 mL) and the mixture stirred at reflux for 15 minutes. 1,2-Diaminobenzene (10 g) is added and the mixture stirred at reflux for 16 hours. The solvent is evaporated and the residue is washed with water and ethanol to afford 18.0 g of the title compound as a beige solid.

Workup

  1. temperatureat reflux for 15 minutes
  2. stirringthe mixture stirred
  3. temperatureat reflux for 16 hours
  4. customThe solvent is evaporated
  5. washthe residue is washed with water and ethanol

Sources & evidence

ORD record
ord-692ad1c1884a401f89e25912f9826ed9
Source dataset
uspto-grants-1996_01
Patent number
US05486517

Reaction notes

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