Dichloromethane → 1-(4-Bromophenyl)-2-phenyl-1H-benzimidazole

HRID 2405454Notes

Reaction equation

HRID 2405454 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.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(OCC)(=O)C.C(Cl)Cl>C1(C)C(C)=CC=CC=1.O>[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 6344DichloromethaneHCID 8857Ethyl AcetateHCID 521998p-Toluenesulfonic acid monohydrateHCID 23160217N-[2-(4-bromophenylamino)phenyl]benzamide

Product 1

HCID 230940711-(4-Bromophenyl)-2-phenyl-1H-benzimidazoleYield 50.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7237O-XyleneSolvent

Procedure

2.1 g (5.7 mmol) of N-[2-(4-bromophenylamino)phenyl]benzamide was suspended in 30 mL of xylene. After the addition of 0.6 g (2.9 mmol) of p-toluenesulfonic acid monohydrate, the mixture was subjected to azeotropic dehydration under reflux for 3 hours. After allowing the reaction solution to cool, ethyl acetate, methylene chloride, and water were added to the reaction solution, and an insoluble component was removed by filtration. The organic phase was extracted from the mother filtrate, washed with water and a saturated sodium chloride solution, and dried over anhydrous sodium sulfate. The solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography to obtain 1.0 g of 1-(4-bromophenyl)-2-phenyl-1H-benzimidazole as a slightly pinkish white crystal (yield: 52%).

Workup

  1. temperatureunder reflux for 3 hours
  2. temperatureto cool
  3. customan insoluble component was removed by filtration
  4. extractionThe organic phase was extracted from the mother filtrate
  5. washwashed with water
  6. dry with materiala saturated sodium chloride solution, and dried over anhydrous sodium sulfate
  7. customThe solvent was then evaporated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-d952ba3e6c864c32aea756558697cbca
Source dataset
uspto-grants-2014_08
Patent number
US08803420B2

Reaction notes

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