Methanol → 2-(5-Ethyl-2-pyridyl)benzimidazole

HRID 1449026Notes

Reaction equation

HRID 1449026 reaction equation
[C:1]1([NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH2:7].[C:9]([C:11]1[CH:16]=[CH:15][C:14]([CH2:17][CH3:18])=[CH:13][N:12]=1)#N.CO.[Na]>C(O)(=O)C>[CH2:17]([C:14]1[CH:15]=[CH:16][C:11]([C:9]2[NH:7][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=3[N:8]=2)=[N:12][CH:13]=1)[CH3:18]

Participants

6

Reactant 4

HCID 887Methanol2×HCID 7243O-PhenylenediamineHCID 5360545SodiumHCID 114463525-Ethylpicolinonitrile

Product 1

HCID 497462-(5-Ethyl-2-pyridyl)benzimidazole

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

1.1 g. of o-phenylenediamine and 1.3 g. of 2-cyano-5-ethylpyridine were dissolved in 5 ml. of methanol. To the solution was added 0.05 g. of sodium in 1 ml. of methanol. The mixture was refluxed for 2 hours, then acidified with acetic acid and refluxed again for an additional 4 hours. The reaction mixture was evaporated.

Workup

  1. additionTo the solution was added 0.05 g
  2. temperatureThe mixture was refluxed for 2 hours
  3. temperaturerefluxed again for an additional 4 hours
  4. customThe reaction mixture was evaporated

Sources & evidence

ORD record
ord-cea8f02790bf4e25a92cfd00a2e2ecbe
Source dataset
uspto-grants-1980_02
Patent number
US04188486

Reaction notes

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