Hydrochloric Acid → 1-Methyl-3,5-diphenylpyrazole

HRID 426560Notes

Reaction equation

HRID 426560 reaction equation
[C:1]([CH2:9][C:10](=O)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:18][NH:19][NH2:20].Cl.C([O-])(=O)C.[Na+]>O.N1C=CC=CC=1>[CH3:18][N:19]1[C:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:9][C:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:20]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6061MethylhydrazineHCID 8433DibenzoylmethaneHCID 517045Sodium Acetate

Product 1

HCID 1405171-Methyl-3,5-diphenylpyrazoleYield 94.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Conditions

Temperature
80 °C

Procedure

545.0 Grams (2.43 moles) of dibenzoylmethane and 533 ml. of pyridine are stirred together and heated to 80° C. 112 Grams (2.43 moles) of methylhydrazine are then slowly added to the mixture and a strong exothermic reaction ensues necessitating cooling of the mixture with a water bath. When addition is complete, the mixture is heated to reflux and maintained in this condition for 40 minutes. The mixture is then cooled to 30° C., poured into 19 liters of 3 N HCl, filtered, and the solid collected. This is reslurried in 198 grams (2.43 moles) of sodium acetate dissolved in 19 liters of water. The mixture is filtered, water washed and air dried to give 535 grams of product, 94.5% yield, having melting point 58° C. to 59° C.

Workup

  1. customa strong exothermic reaction
  2. temperatureensues necessitating cooling of the mixture with a water bath
  3. additionWhen addition
  4. temperaturethe mixture is heated
  5. temperatureto reflux
  6. temperaturemaintained in this condition for 40 minutes
  7. temperatureThe mixture is then cooled to 30° C.
  8. filtrationfiltered
  9. customthe solid collected
  10. filtrationThe mixture is filtered
  11. washwater washed
  12. customair dried

Sources & evidence

ORD record
ord-8f2b71ce04214e3386ae04c1fc2ee211
Source dataset
uspto-grants-1979_10
Patent number
US04170464

Reaction notes

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