HCID 85997294, compound → HCID 23094069, compound

HRID 420472Notes

Reaction equation

HRID 420472 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[C:6]([CH:16]=1)[NH:7][C:8](=O)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1>C1(C)C(C)=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:17]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:8]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=3)=[N:7][C:6]=2[CH:16]=1

Participants

3

Reactant 1

HCID 85997294HCID 85997294, compound2×

Product 1

HCID 23094069HCID 23094069, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

Suspending 3.1 g (8.4 mmol) of 5′-bromo-2′-(N-phenylamino)-picoline anilide obtained in the above step (1) into 30 milliliter of xylene, and adding 0.48 g (2.5 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 the use of magnesium sulfuric anhydride, followed by removing the solvent by distillation under reduced pressure, 2.0 g of 5-bromo-1-phenyl-2-(2-pyridyl)-1H-benzimidazole was obtained (yield: 69%).

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 the use of magnesium sulfuric anhydride
  7. customby removing the solvent
  8. distillationby distillation under reduced pressure

Sources & evidence

ORD record
ord-bd6ea8c6817e4727b0226e2af412ae79
Source dataset
uspto-grants-2012_01
Patent number
US08097349B2

Reaction notes

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