O-Phenylenediamine → 2-(6-methylpyridin-3-yl)-1H-benzimidazole

HRID 1449021Notes

Reaction equation

HRID 1449021 reaction equation
[C:1]1([NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH2:7].[CH3:9][C:10]1[CH:15]=[CH:14][C:13]([C:16](O)=O)=[CH:12][N:11]=1.C(=O)([O-])[O-].[Na+].[Na+]>O>[CH3:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[NH:7][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=3[N:8]=2)=[CH:12][N:11]=1

Participants

5

Reactant 3

HCID 7243O-PhenylenediamineHCID 10340Sodium CarbonateHCID 1378606-Methylnicotinic acid

Product 1

HCID 7543762-(6-methylpyridin-3-yl)-1H-benzimidazole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

11.9 g. of o-phenylenediamine, 13.7 g. of 2-methylpyridine-5-carboxylic acid and 100 g. of polyphosphoric acid were stirred under a nitrogen gas current at 180° C. to 200° C. for 4 hours. To the reaction mixture were added 800 ml. of water and then a concentrated aqueous solution of sodium carbonate to neutrality. The resulting crystals were filtered off, dried and recrystallized from acetonitrile to give 15.7 g. of colorless needles of the product (75% of theory), M.P. 265.5°-266.0° C.

Workup

  1. additionTo the reaction mixture were added 800 ml
  2. filtrationThe resulting crystals were filtered off
  3. customdried
  4. customrecrystallized from acetonitrile
  5. customto give 15.7 g

Sources & evidence

ORD record
ord-9ab65bc9ccc64aeebdc51669c83452d2
Source dataset
uspto-grants-1980_02
Patent number
US04188486

Reaction notes

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