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

HRID 1172774
Notes
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Reaction equation

HRID 1172774 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.O.C1(C)C=CC(S(O)(=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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 7237O-XyleneHCID 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 962
Water
Solvent
HCID 6344DichloromethaneSolvent

Procedure

2.1 g (5.7 mmol) of N-[2-(4-bromophenylamino)phenyl]benzamide were suspended into 30 mL of xylene, 0.6 g (2.9 mmol) of p-toluenesulfonic acid monohydrate was added, and the whole was refluxed under heating for 3 hours. After the resultant had been stood to cool, the reaction solution was added with ethyl acetate, dichloromethane, and water for filtering insoluble matter out. An organic layer was extracted from a mother liquor, washed with water and a saturated sodium chloride solution, and dried with anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by means of silica gel column chromatography to obtain 1.0 g of 1-(4-bromophenyl)-2-phenyl-1H-benzimidazole (52% yield).

Workup

  1. additionwas added
  2. temperaturethe whole was refluxed
  3. temperatureunder heating for 3 hours
  4. temperatureto cool
  5. filtrationfor filtering insoluble matter out
  6. extractionAn organic layer was extracted from a mother liquor
  7. washwashed with water
  8. dry with materiala saturated sodium chloride solution, and dried with anhydrous sodium sulfate
  9. distillationthe solvent was distilled off under reduced pressure
  10. customThe residue was purified by means of silica gel column chromatography

Sources & evidence

ORD record
ord-84a522a111994de28722d0611d40d82f
Source dataset
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07833632B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes