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

HRID 2274132Notes

Reaction equation

HRID 2274132 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 52%

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. To the resulting suspension, 0.6 g (2.9 mmol) of p-toluenesulfonic acid monohydrate was added, and the resultant was subjected to azeotropic dehydration while heating under reflux for 3 hours. After allowing it to be cool, ethyl acetate, methylene chloride and water were added to the reaction solution, and unsoluble matters were filtered off. An organic phase was extracted from a mother solution, washed with water and saturated saline, and dried with anhydrous sodium sulfate. The solvent was distilled off under a reduced pressure. Residues were purified by silica gel column chromatography, whereby 1.0 g of slightly pinky white crystals of 1-(4-bromophenyl)-2-phenyl-1H-benzimidazole were obtained (yield 52%).

Workup

  1. temperaturewhile heating
  2. temperatureunder reflux for 3 hours
  3. temperatureto be cool
  4. filtrationwere filtered off
  5. extractionAn organic phase was extracted from a mother solution
  6. washwashed with water and saturated saline
  7. dry with materialdried with anhydrous sodium sulfate
  8. distillationThe solvent was distilled off under a reduced pressure
  9. customResidues were purified by silica gel column chromatography, whereby 1.0 g of slightly pinky white crystals of 1-(4-bromophenyl)-2-phenyl-1H-benzimidazole
  10. customwere obtained (yield 52%)

Sources & evidence

ORD record
ord-07a8aea0033a413f898cff2f937b00ee
Source dataset
uspto-grants-2015_09
Patent number
US09126943B2

Reaction notes

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