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

HRID 420471Notes

Reaction equation

HRID 420471 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.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 6101p-Toluenesulfonic acidHCID 230940734'-bromo-N-methyl-2'-aminobenzanilide

Product 1

HCID 230940805-Bromo-1-methyl-2-phenyl-1H-benzo[d]imidazoleYield 87.1%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

Suspending 7.8 g (26 mmol) of 4′-bromo-N-methyl-2′-amino-benzanilide obtained in the above step (3) into 50 milliliter of xylene, and adding 1.5 g (7.7 mmol) of p-toluenesulfonic acid 1 hydrate, the resultant solution was refluxed with heating for 7 hours. After completing the reaction, the resultant solution was filtered. Dissolving the resultant solids into methylene chloride, the resultant solution was washed with 10% K2CO3 aqueous solution and with a saturated solution of sodium chloride, and then, after drying with the use of magnesium sulfate, the solvent was removed by distillation. Washing the filtrate with 10% K2CO3 aqueous solution and with saturated solution of sodium chloride, and then, after drying with the use of magnesium sulfate, the solvent was removed by distillation. Combining the above two kinds of residues after removing by distillation, the resultant product was refined with silicagel column chromatography, 6.50 g of 5-bromo-1-methyl-2-phenyl-1H-benzimidazole was obtained as white solids (yield: 89%).

Workup

  1. temperaturewith heating for 7 hours
  2. customthe reaction
  3. filtrationthe resultant solution was filtered
  4. dissolutionDissolving the resultant solids into methylene chloride
  5. washthe resultant solution was washed with 10% K2CO3 aqueous solution and with a saturated solution of sodium chloride
  6. dry with materialafter drying with the use of magnesium sulfate
  7. customthe solvent was removed by distillation
  8. washWashing the filtrate with 10% K2CO3 aqueous solution
  9. dry with materialwith saturated solution of sodium chloride, and then, after drying with the use of magnesium sulfate
  10. customthe solvent was removed by distillation
  11. customafter removing by distillation

Sources & evidence

ORD record
ord-10259f3fe7bd47a79b208c3526ae7a2f
Source dataset
uspto-grants-2012_01
Patent number
US08097349B2

Reaction notes

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