2-Acetylpyridine → HCID 86589147, compound

HRID 2216943Notes

Reaction equation

HRID 2216943 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=1)(=O)[CH3:2].[C:10]1([N:16]2[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=3[N:18]=[C:17]2[NH:25][NH2:26])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>CO.C(O)(=O)C>[C:10]1([N:16]2[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=3[N:18]=[C:17]2[NH:25][N:26]=[C:1]([C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=2)[CH3:2])[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 2

HCID 142862-AcetylpyridineHCID 13984431HCID 13984431, compound

Product 1

HCID 86589147HCID 86589147, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 887MethanolSolvent

Procedure

A mixture of 2-acetyl pyridine (1.00 g, 8.26 mmol) and 1-phenyl-2-hydrazinobenzimidazole (1.85 g, 8.26 mmol) in 20 ml of methanol is stirred at room temperature for 2 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 50% methanol, and dried. The product is recrystallized from a mixture of methanol and water. Yield: 1.35 g (50% 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 50% methanol
  6. customdried
  7. customThe product is recrystallized from a mixture of methanol and water

Sources & evidence

ORD record
ord-0a9515790ce6496091266ae0a406a05c
Source dataset
uspto-grants-2006_09
Patent number
US07112680B2

Reaction notes

Loading…