O-Phenylenediamine → 2-(5-Ethyl-2-pyridyl)benzimidazole

HRID 1449023Notes

Reaction equation

HRID 1449023 reaction equation
[C:1]1([NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH2:7].[CH2:9]([C:11]1[CH:12]=[CH:13][C:14]([CH3:17])=[N:15][CH:16]=1)[CH3:10].[S]>>[CH2:9]([C:11]1[CH:12]=[CH:13][C:14]([C:17]2[NH:7][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=3[N:8]=2)=[N:15][CH:16]=1)[CH3:10]

Participants

4

Reactant 3

HCID 7243O-PhenylenediamineHCID 77285-Ethyl-2-methylpyridineHCID 5362487Sulfur

Product 1

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

Procedure

130 g. of o-phenylenediamine, 121 g. of 5-ethyl-2-methylpyridine and 96 g. of sulfur were heated at 160°-170° C. for 20 hours. The reaction mixture was dissolved in 2,000 ml. of chloroform and the solution was washed with water and 6 N hydrochloric acid successively. Chloroform was removed by evaporation in vacuo. The residue was subjected to silica gel column chromatography and recrystallized from ethyl acetate. The product showed no melting point depression upon mixing with the product of the preceding example. Yield, 137 g (61% of theory).

Workup

  1. dissolutionThe reaction mixture was dissolved in 2,000 ml
  2. washof chloroform and the solution was washed with water and 6 N hydrochloric acid successively
  3. customChloroform was removed by evaporation in vacuo
  4. customrecrystallized from ethyl acetate
  5. customYield

Sources & evidence

ORD record
ord-9121c27f21374dc2b656ff17d095c7e8
Source dataset
uspto-grants-1980_02
Patent number
US04188486

Reaction notes

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