p-Toluenesulfonic acid → 2-(4-Bromophenyl)-1-phenyl-1H-benzo(d)imidazole

HRID 2354523Notes

Reaction equation

HRID 2354523 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.[Br:15][C:16]1[CH:23]=[CH:22][C:19]([CH:20]=O)=[CH:18][CH:17]=1.CC1C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Br:15][C:16]1[CH:23]=[CH:22][C:19]([C:20]2[N:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[N:14]=2)=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 68297N-Phenyl-o-phenylenediamineHCID 707414-Bromobenzaldehyde

Product 1

HCID 230940702-(4-Bromophenyl)-1-phenyl-1H-benzo(d)imidazoleYield 57.71%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

N-Phenyl-o-phenylenediamine 13.27 g (72 mmole), 4-bromobenzaldehyde 16 g (87 mmole), and 2.8 g of PTSA (14 mmole) was stirred in 150 ml of Toluene, the reaction mixture was then heated to reflux for 16 hours, after cooling, the reaction mixture was extracted with water, and then the organic layer was evaporated to dry, the residue was then recrystallized with acetone to get 14.51 g of product (yield=57.71%).

Workup

  1. temperaturethe reaction mixture was then heated
  2. temperatureto reflux for 16 hours
  3. temperatureafter cooling
  4. extractionthe reaction mixture was extracted with water
  5. customthe organic layer was evaporated
  6. customto dry
  7. customthe residue was then recrystallized with acetone

Sources & evidence

ORD record
ord-239ca4b44dfa40a2a47b3555eadecfbc
Source dataset
uspto-grants-2010_07
Patent number
US07754348B2

Reaction notes

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