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

HRID 1031156Notes

Reaction equation

HRID 1031156 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-cd9290ee10e949e2acaef56d7e03cabe
Source dataset
uspto-grants-1992_04
Patent number
US05109012

Reaction notes

Loading…