HCID 23094072, compound → HCID 23094067, compound

HRID 420467Notes

Reaction equation

HRID 420467 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:6]([CH:11]=1)[NH:7][C:8](=O)[CH3:9]>C1(C)C(C)=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:8]([CH3:9])=[N:7][C:6]=2[CH:11]=1

Participants

3

Reactant 1

HCID 23094072HCID 23094072, compound2×

Product 1

HCID 23094067HCID 23094067, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

Suspending 3.6 g (12 mmol) of 5′-bromo-2′-(N-phenylamino)-acetanilide obtained in the above step (1) into 30 milliliter of xylene, and adding 0.68 g (3.6 mmol) of p-toluenesulfonic acid 1 hydrate, the resultant solution was azeotropically dehydrated while refluxing with heating for 5 hours. The reacted solution was cooled down to room temperature, and the solvent was removed by distillation. Dissolving the resultant solid into ethyl acetate, and after sequentially washing with water, with 10% potassium carbonate aqueous solution and with saturated solution of sodium chloride, it was dried with sulfuric anhydride magnesium, followed by removing the solvent by distillation under reduced pressure, 3.0 g of 5-bromo-2-methyl-1-phenyl-1H-benzimidazole was obtained (yield: 90%).

Workup

  1. temperaturewhile refluxing
  2. temperaturewith heating for 5 hours
  3. customthe solvent was removed by distillation
  4. dissolutionDissolving the resultant solid into ethyl acetate
  5. washafter sequentially washing with water, with 10% potassium carbonate aqueous solution and with saturated solution of sodium chloride, it
  6. dry with materialwas dried with sulfuric anhydride magnesium
  7. customby removing the solvent
  8. distillationby distillation under reduced pressure

Sources & evidence

ORD record
ord-3a74383c056c43e9b55a663ecbb39ba9
Source dataset
uspto-grants-2012_01
Patent number
US08097349B2

Reaction notes

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