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

HRID 2216940Notes

Reaction equation

HRID 2216940 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][N:7]=[CH:6][N:5]=1)(=O)[CH3:2].[NH:10]([C:12]1[NH:13][C:14]2[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=2[N:16]=1)[NH2:11]>CO.C(O)(=O)C>[NH:13]1[C:14]2[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=2[N:16]=[C:12]1[NH:10][N:11]=[C:1]([C:4]1[CH:9]=[CH:8][N:7]=[CH:6][N:5]=1)[CH3:2]

Participants

5

Reactant 2

HCID 957882-hydrazinyl-1H-1,3-benzodiazoleHCID 5380601-(Pyrimidin-4-yl)ethanone

Product 1

HCID 3965961-(4-Pyrimidinyl)-1-ethanone-1-(1H-benzo[d]imidazol-2-yl)-hydrazone

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 887MethanolSolvent

Procedure

A mixture of 4-acetyl pyrimidine (0.412 g, 3.37 mmol) and 2-hydrazinobenzimidazole (0.50 g, 3.37 mmol) in 15 ml of methanol is refluxed after the addition of 5 drops of glacial acetic acid, until monitoring of the reaction by means of thin layer chromatography (Polygram Sil G/UV254 prefabricated foils; eluting agent: CH2Cl2:MeOH (10:1)) did not reveal any further reaction. The reaction mixture is stored over night in the refrigerator at approximately 5° C. The precipitate is filtered and recrystallized from a mixture of ethyl acetate and diisopropyl ether. Yield: 0.65 g (76% of theory).

Workup

  1. temperatureis refluxed
  2. customuntil monitoring of the reaction
  3. washby means of thin layer chromatography (Polygram Sil G/UV254 prefabricated foils; eluting agent: CH2Cl2:MeOH (10:1))
  4. customany further reaction
  5. waitThe reaction mixture is stored over night in the refrigerator at approximately 5° C
  6. filtrationThe precipitate is filtered
  7. customrecrystallized from a mixture of ethyl acetate and diisopropyl ether

Sources & evidence

ORD record
ord-5240fdcc2ced43c694813d50576c545a
Source dataset
uspto-grants-2006_09
Patent number
US07112680B2

Reaction notes

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