O-Xylene → HCID 23094081, compound

HRID 420457Notes

Reaction equation

HRID 420457 reaction equation
N1C=CC=CC=1NC1C=CC=CC=1C(N[C:13]1[CH:18]=[CH:17][C:16]([Br:19])=[CH:15][CH:14]=1)=O.[N+:24]([C:27]1[CH:39]=[CH:38][CH:37]=[CH:36][C:28]=1[NH:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=1)([O-])=O.[C:40]1(C)C(C)=CC=CC=1>>[N:31]1[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=1[N:29]1[C:28]2[CH:36]=[CH:37][CH:38]=[CH:39][C:27]=2[N:24]=[C:40]1[C:13]1[CH:14]=[CH:15][C:16]([Br:19])=[CH:17][CH:18]=1

Participants

4

Reactant 3

HCID 7237O-XyleneHCID 23094082HCID 23094082, compoundHCID 59785875N-(2-Nitrophenyl)pyridin-2-amine

Product 1

HCID 23094081HCID 23094081, compoundYield 67%

Procedure

Suspending 5.5 g (15.0 mmol) of 2-(2-pyridylamino)-4′-bromobenzanilide obtained in the above step (2) into 60 milliliter of xylene, and adding 0.86 g (4.5 mmol) of p-toluenesulfonic acid 1 hydrate, the resultant solution was azeotropically dehydrated while refluxing with heating for 8 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, 3.5 g of 1-(2-pyridyl)-2-(4-bromophenyl)-1H-benzimidazole was obtained (yield: 67%).

Workup

  1. temperaturewhile refluxing
  2. temperaturewith heating for 8 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-6d4d4d00fc854a2995ae8383b458c7fa
Source dataset
uspto-grants-2012_01
Patent number
US08097349B2

Reaction notes

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