2-Acetylpyridine → 1-(2-Pyridyl)-1-ethanon-1(1H-benzo[d]imidazol-2-yl)hydrazone

HRID 2216936Notes

Reaction equation

HRID 2216936 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=1)(=O)[CH3:2].[NH:10]([C:12]1[NH:13][C:14]2[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=2[N:16]=1)[NH2:11]>CO.C(O)(=O)C>[NH:13]1[C:14]2[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=2[N:16]=[C:12]1[NH:10][N:11]=[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=1)[CH3:2]

Participants

5

Reactant 2

HCID 142862-AcetylpyridineHCID 957882-hydrazinyl-1H-1,3-benzodiazole

Product 1

HCID 48531461-(2-Pyridyl)-1-ethanon-1(1H-benzo[d]imidazol-2-yl)hydrazone

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 887MethanolSolvent

Procedure

A mixture of 2-acetyl pyridine (1.00 g, 8.25 mmol) and 2-hydrazinobenzimidazole (1.22 g, 8.25 mmol) in 20 ml of methanol is stirred for 3 days at room temperature after addition of 6 drops of glacial acetic acid. The reaction is monitored by means of thin layer chromatography (Polygram Sil G/UV254 prefabricated foils; eluting agent: CH2Cl2:MeOH (12:1)). Subsequently, the reaction mixture is diluted with distilled water until a precipitate forms and stored in the refrigerator at approximately 5° C. for 24 hours. The precipitate is filtered, washed several times with 50% methanol, and dried. The product is recrystallized from a mixture of ethyl acetate and diisopropyl ether. Yield: 1.45 g (70% of theory).

Workup

  1. washThe reaction is monitored by means of thin layer chromatography (Polygram Sil G/UV254 prefabricated foils; eluting agent: CH2Cl2:MeOH (12:1))
  2. additionSubsequently, the reaction mixture is diluted with distilled water until a precipitate forms
  3. waitstored in the refrigerator at approximately 5° C. for 24 hours
  4. filtrationThe precipitate is filtered
  5. washwashed several times with 50% methanol
  6. customdried
  7. customThe product is recrystallized from a mixture of ethyl acetate and diisopropyl ether

Sources & evidence

ORD record
ord-99acbaf0ca9f466486cbe4fcf7517dd3
Source dataset
uspto-grants-2006_09
Patent number
US07112680B2

Reaction notes

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