Acetylacetone → Pyrazole-1-carboxamidine, 3,5-dimethyl-, monohydrochloride

HRID 2395219Notes

Reaction equation

HRID 2395219 reaction equation
[C:1]([NH:4][NH2:5])([NH2:3])=[NH:2].[ClH:6].[CH3:7][C:8]([CH2:10][C:11]([CH3:13])=O)=O>C(O)C>[ClH:6].[C:1]([N:4]1[C:11]([CH3:13])=[CH:10][C:8]([CH3:7])=[N:5]1)(=[NH:3])[NH2:2]

Participants

4

Reactant 2

HCID 31261AcetylacetoneHCID 178418668HCID 178418668, compound

Product 1

HCID 218002Pyrazole-1-carboxamidine, 3,5-dimethyl-, monohydrochloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 850 ml of ethanol were added 188 g of aminoguanidine hydrochloride and 170 g of 2,4-pentadione and the mixture was heated with stirring for 3 hrs. under reflux. The precipitated crystals were filtered, sufficiently washed with ethanol and dried to obtain 1-amidino-3,5-dimethylpyrazole hydrochloride of 210 g. Next, 60 g of potassium hydroxide was dissolved in water of 120 g and 1-amidino-3,5-dimethylpyrazole hydrochloride of 61.1 g was added thereto withcooling with water and stirred further for 1 hr. Chloroform of 200 ml was added to the solution for extraction. A chloroform layer was separated, washed with water and dried with anhydrous sodium sulfate, thereafter, chloroform was removed to obtain 1-amidino-3,5-dimethylpyrazole of 46.0 g.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux
  3. filtrationThe precipitated crystals were filtered
  4. washsufficiently washed with ethanol
  5. customdried

Sources & evidence

ORD record
ord-6e4a46c9168b4937af9c4670035661f1
Source dataset
uspto-grants-1998_09
Patent number
US05814580

Reaction notes

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