2-hydrazinyl-1-methyl-1H-1,3-benzodiazole → 1-(4-Chloro-2-pyridyl)-1-ethanone-1-(1-methyl-1H-benzo[d]imidazol-2-yl)-hydrazone

HRID 2216945Notes

Reaction equation

HRID 2216945 reaction equation
[C:1]([C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][N:5]=1)(=O)[CH3:2].[CH3:11][N:12]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[N:14]=[C:13]1[NH:21][NH2:22]>CO.C(O)(=O)C>[CH3:11][N:12]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[N:14]=[C:13]1[NH:21][N:22]=[C:1]([C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][N:5]=1)[CH3:2]

Participants

5

Reactant 2

HCID 15222652-hydrazinyl-1-methyl-1H-1,3-benzodiazoleHCID 130119861-(4-Chloro-pyridin-2-yl)-ethanone

Product 1

HCID 865891491-(4-Chloro-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-4-chloropyridine (0.50 g, 3.20 mmol) and 1-methyl-2-hydrazinobenzimidazole (0.52 g, 3.20 mmol) in 5 ml of methanol is stirred for 4 days at room temperature 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 the 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: 0.60 g (62% 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 the 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-45b5a9ed9fcf4c34962d83cdecb29975
Source dataset
uspto-grants-2006_09
Patent number
US07112680B2

Reaction notes

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