O-Phenylenediamine → 2-(6-chloropyridin-3-yl)-1H-1,3-benzodiazole

HRID 499155Notes

Reaction equation

HRID 499155 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=O)=[CH:4][N:3]=1.[C:11]1([NH2:18])[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[NH2:17].C([O-])(O)=O.[Na+]>O>[Cl:1][C:2]1[N:3]=[CH:4][C:5]([C:6]2[NH:18][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N:17]=2)=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 7243O-PhenylenediamineHCID 792226-Chloronicotinic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 14883902-(6-chloropyridin-3-yl)-1H-1,3-benzodiazoleYield 40%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 6-chloronicotinic acid (0.785 g, 5.000 mmol) and o-phenylenediamine (0.540 g, 5.000 mmol) was added to pre-heated (150° C.) polyphosphoric acid (5 g) with stirring. The stirring was continued at 150° C. overnight. Water was added to the reaction mixture, and the resulting solution was neutralized with NaHCO3, and extracted with ethyl acetate. The organic phase was dried and evaporated to afford 2-(6-chloropyridin-3-yl)-1H-benzoimidazole in 40% yield (0.468 g, 2.04 mmol).

Workup

  1. additionwas added
  2. extractionextracted with ethyl acetate
  3. customThe organic phase was dried
  4. customevaporated

Sources & evidence

ORD record
ord-6c93e7c87fe2486f9f6f310b3eb6e03a
Source dataset
uspto-grants-2010_08
Patent number
US07767677B2

Reaction notes

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