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

HRID 2216944Notes

Reaction equation

HRID 2216944 reaction equation
[C:1]([C:4]1[C:9]([O:10][CH3:11])=[CH:8][CH:7]=[CH:6][N:5]=1)(=O)[CH3:2].[CH3:12][N:13]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[N:15]=[C:14]1[NH:22][NH2:23]>CO.C(O)(=O)C>[CH3:12][N:13]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[N:15]=[C:14]1[NH:22][N:23]=[C:1]([C:4]1[C:9]([O:10][CH3:11])=[CH:8][CH:7]=[CH:6][N:5]=1)[CH3:2]

Participants

5

Reactant 2

HCID 15222652-hydrazinyl-1-methyl-1H-1,3-benzodiazoleHCID 219460561-(3-Methoxypyridin-2-yl)ethan-1-one

Product 1

HCID 865891481-(3-Methoxy-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-3-methoxypyridine (0.50 g, 3.31 mmol) and 1-methyl-2-hydrazinobenzimidazole (0.54 g, 3.31 mmol) in 10 ml of methanol is stirred at room temperature for 3 days 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 20 ml of methanol and 10 ml of water. Yield: 0.87 g (89% 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 20 ml of methanol and 10 ml of water

Sources & evidence

ORD record
ord-f8f22094ef404cd5a5d524b05bafc0f6
Source dataset
uspto-grants-2006_09
Patent number
US07112680B2

Reaction notes

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