2-hydrazinyl-1-methyl-1H-1,3-benzodiazole → 379226-93-4

HRID 2216946Notes

Reaction equation

HRID 2216946 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[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]=[CH:8][C:7]([CH3:10])=[CH:6][N:5]=1)[CH3:2]

Participants

5

Reactant 2

HCID 15222652-hydrazinyl-1-methyl-1H-1,3-benzodiazoleHCID 130686631-(5-Methyl-2-pyridinyl)ethanone

Product 1

HCID 72801354379226-93-4

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 887MethanolSolvent

Procedure

A mixture of 2-acetyl-5-methylpyridine (1.00 g, 7.40 mmol) and 1-methyl-2-hydrazinobenzimidazole (1.20 g, 7.40 mmol) in 20 ml of methanol is stirred for 3 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/UV234 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 50% methanol, and dried. The product is recrystallized from a mixture of methanol and water: Yield: 1.54 g (73% of theory).

Workup

  1. washThe reaction is monitored by means of thin layer chromatography (Polygram Sil G/UV234 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 50% methanol
  6. customdried
  7. customThe product is recrystallized from a mixture of methanol and water

Sources & evidence

ORD record
ord-1585483c303640ebb946073189b98f65
Source dataset
uspto-grants-2006_09
Patent number
US07112680B2

Reaction notes

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