p-Toluenesulfonic acid monohydrate → 5-Bromo-1-methyl-2-phenyl-1H-benzo[d]imidazole

HRID 1172770Notes

Reaction equation

HRID 1172770 reaction equation
[Br:1][C:2]1[CH:17]=[CH:16][C:5]([N:6]([CH3:15])[C:7](=O)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[C:4]([NH2:18])[CH:3]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C(C)=CC=CC=1>[Br:1][C:2]1[CH:17]=[CH:16][C:5]2[N:6]([CH3:15])[C:7]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)=[N:18][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 230940734'-bromo-N-methyl-2'-aminobenzanilide

Product 1

HCID 230940805-Bromo-1-methyl-2-phenyl-1H-benzo[d]imidazoleYield 89%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

7.8 g (26 mmol) of 4′-bromo-N-methyl-2′-amino-benzanilide were suspended into 50 mL of xylene. Then, 1.5 g (7.7 mmol) of p-toluenesulfonic acid monohydrate was added, and the whole was refluxed under heating for 7 hours. After the completion of the reaction, the resultant was filtered. The resultant solid was dissolved into methylene chloride, washed with 10-mass % K2CO3 and a saturated sodium chloride solution, and dried with magnesium sulfate. After that, the solvent was distilled off under reduced pressure. The filtrate was washed with 10-mass % K2CO3 and a saturated sodium chloride solution, and dried with magnesium sulfate. After that, the solvent was distilled off under reduced pressure. The resultant two residues were coalesced, and the resultant was purified by means of silica gel column chromatography to obtain 6.5 g of 5-bromo-1-methyl-2-phenyl-1H-benzimidazole as a white solid (89% yield).

Workup

  1. temperaturethe whole was refluxed
  2. temperatureunder heating for 7 hours
  3. customAfter the completion of the reaction
  4. filtrationthe resultant was filtered
  5. dissolutionThe resultant solid was dissolved into methylene chloride
  6. washwashed with 10-mass % K2CO3
  7. dry with materiala saturated sodium chloride solution, and dried with magnesium sulfate
  8. distillationAfter that, the solvent was distilled off under reduced pressure
  9. washThe filtrate was washed with 10-mass % K2CO3
  10. dry with materiala saturated sodium chloride solution, and dried with magnesium sulfate
  11. distillationAfter that, the solvent was distilled off under reduced pressure
  12. customthe resultant was purified by means of silica gel column chromatography

Sources & evidence

ORD record
ord-97d4f9474ef84625bf5494aa7726bca9
Source dataset
uspto-grants-2010_11
Patent number
US07833632B2

Reaction notes

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