p-Toluenesulfonic acid → 2-(4-Bromophenyl)benzimidazole

HRID 2354527Notes

Reaction equation

HRID 2354527 reaction equation
[C:1]1([NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH2:7].[Br:9][C:10]1[CH:17]=[CH:16][C:13]([CH:14]=O)=[CH:12][CH:11]=1.CC1C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Br:9][C:10]1[CH:17]=[CH:16][C:13]([C:14]2[NH:8][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=3[N:7]=2)=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 7243O-PhenylenediamineHCID 707414-Bromobenzaldehyde

Product 1

HCID 2861822-(4-Bromophenyl)benzimidazoleYield 64.54%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

o-Phenylenediamine 7.79 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 12.69 g of product (yield=64.54%).

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-8046d73dfc0346a29c2b0d01b546bd98
Source dataset
uspto-grants-2010_07
Patent number
US07754348B2

Reaction notes

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