2-hydrazinyl-1-methyl-1H-1,3-benzodiazole → 1-(6-Phenyl-2-pyridyl)-1-ethanone-1-(1-methyl-1H-benzo[d]imidazol-2-yl)-hydrazone

HRID 2216947Notes

Reaction equation

HRID 2216947 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:5]=1)(=O)[CH3:2].[CH3:16][N:17]1[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[N:19]=[C:18]1[NH:26][NH2:27]>CO.C(O)(=O)C>[CH3:16][N:17]1[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[N:19]=[C:18]1[NH:26][N:27]=[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:5]=1)[CH3:2]

Participants

5

Reactant 2

HCID 15222652-hydrazinyl-1-methyl-1H-1,3-benzodiazoleHCID 154979432-Acetyl-6-phenylpyridine

Product 1

HCID 865891501-(6-Phenyl-2-pyridyl)-1-ethanone-1-(1-methyl-1H-benzo[d]imidazol-2-yl)-hydrazone

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 887MethanolSolvent

Procedure

A mixture of 2-acetyl-6-phenylpyridine (0.50 g, 2.53 mmol) and 1-methyl-2-hydrazinobenzimidazole (0.41 g, 2.53 mmol) in 10 ml of methanol is stirred at room temperature for 12 hours after the 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 for 24 hours in a refrigerator at approximately 5° C. The precipitate is filtered, washed several times with water, and dried. The product is recrystallized from a mixture of methanol and water. Yield: 0.51 g (59% 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 for 24 hours in a refrigerator at approximately 5° C
  4. filtrationThe precipitate is filtered
  5. washwashed several times with water
  6. customdried
  7. customThe product is recrystallized from a mixture of methanol and water

Sources & evidence

ORD record
ord-e84472e66acb49239b4168c7e2567148
Source dataset
uspto-grants-2006_09
Patent number
US07112680B2

Reaction notes

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