O-Xylene → 1-(4-Bromophenyl)-2-phenyl-1H-benzimidazole

HRID 420461Notes

Reaction equation

HRID 420461 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[NH:15][C:16](=O)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:4][CH:3]=1.C1(C)C(C)=CC=CC=1.BrC1C=CC(NC2C=CC=CC=2[N+]([O-])=O)=CC=1.C(OCC)(=O)C>O.ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[N:15]=[C:16]2[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 7237O-XyleneHCID 8857Ethyl AcetateHCID 12000290N-(4-bromophenyl)-2-nitroanilineHCID 23160217N-[2-(4-bromophenylamino)phenyl]benzamide

Product 1

HCID 230940711-(4-Bromophenyl)-2-phenyl-1H-benzimidazoleYield 52%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Suspending 2.1 g (5.7 mmol) of N-[2-(4-bromophenylamino)phenyl]benzamide obtained in the above step (2) into 30 milliliter of xylene, and adding 0.6 g (2.9 mmol) of p-toluenesulfonic acid 1 hydrate, the resultant solution was azeotropically dehydrated while refluxing with heating for 3 hours. After naturally cooling the reacted solution, ethyl acetate, dichloromethane and water were added to the reacted solution, followed by separating an insoluble substance by filtration. Extracting an organic layer from mother liquor, the organic layer was washed with water and a saturated solution of sodium chloride and then, dried with anhydrous sodium sulfate, followed by removing the solvent by distillation under reduced pressure. Refining the residue with silicagel column chromatography, 1.0 g of 1-(4-bromophenyl)-2-phenyl-1H-benzimidazole was obtained as white crystals with a slight pink color (yield: 52%).

Workup

  1. temperaturewhile refluxing
  2. temperaturewith heating for 3 hours
  3. additionwere added to the reacted solution
  4. customby separating an insoluble substance
  5. filtrationby filtration
  6. extractionExtracting an organic layer from mother liquor
  7. washthe organic layer was washed with water
  8. dry with materiala saturated solution of sodium chloride and then, dried with anhydrous sodium sulfate
  9. customby removing the solvent
  10. distillationby distillation under reduced pressure

Sources & evidence

ORD record
ord-41b512548d3d4d268ebf68a5c4e481d4
Source dataset
uspto-grants-2012_01
Patent number
US08097349B2

Reaction notes

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