Sulfuric Acid → 1H-Pyrazole, 1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-3,5-dimethyl-

HRID 2082388Notes

Reaction equation

HRID 2082388 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([Cl:12])[C:3]=1[NH:13][NH2:14].[CH3:15][C:16](=O)[CH2:17][C:18](=O)[CH3:19].S(=O)(=O)(O)O>C(O)C>[CH3:15][C:16]1[CH:17]=[C:18]([CH3:19])[N:13]([C:3]2[C:2]([Cl:1])=[CH:7][C:6]([C:8]([F:9])([F:11])[F:10])=[CH:5][C:4]=2[Cl:12])[N:14]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 31261AcetylacetoneHCID 688223[2,6-Dichloro-4-(trifluoromethyl)phenyl]hydrazine

Product 1

HCID 27410921H-Pyrazole, 1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-3,5-dimethyl-

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2,6-dichloro-4-trifluoromethylphenylhydrazine (5.0 g), 2,4-pentanedione (2.1 ml) and conc. sulphuric acid (0.8 ml) in ethanol (40 ml) was heated under reflux for 20 hours. The ethanol was evaporated under reduced pressure and the residue dissolved in dichloromethane. The extract was washed with sodium bicarbonate solution and brine, dried over magnesium sulphate and evaporated to give 3,5-dimethyl-1-(2,6-dichloro-4-trifluoromethylphenyl)-1H-pyrazole.

Workup

  1. temperatureunder reflux for 20 hours
  2. customThe ethanol was evaporated under reduced pressure
  3. dissolutionthe residue dissolved in dichloromethane
  4. washThe extract was washed with sodium bicarbonate solution and brine
  5. dry with materialdried over magnesium sulphate
  6. customevaporated

Sources & evidence

ORD record
ord-347a76e3947643de83937f8f045fa5ec
Source dataset
uspto-grants-1993_02
Patent number
US05189053

Reaction notes

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