Dichloromethane → 1-Ethyl-5-methyl-3-(trifluoromethyl)-1H-pyrazole

HRID 963143Notes

Reaction equation

HRID 963143 reaction equation
C(O)(=O)C(O)=O.[CH2:7]([NH:9][NH2:10])[CH3:8].[F:11][C:12]([F:20])([F:19])[C:13](=O)[CH2:14][C:15](=O)[CH3:16].ClCCl>C(O)C>[CH2:7]([N:9]1[C:15]([CH3:16])=[CH:14][C:13]([C:12]([F:20])([F:19])[F:11])=[N:10]1)[CH3:8]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 739431,1,1-Trifluoro-2,4-pentanedioneHCID 96181Hydrazine, ethyl-, ethanedioate (1:1)

Product 1

HCID 147706511-Ethyl-5-methyl-3-(trifluoromethyl)-1H-pyrazole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of 25.0 g (grams) (167 mmol) (millimoles) of ethylhydrazine oxalate in 50 mL (milliliters) of ethanol was added to a solution of 25.0 g (162 mmol) of 1,1,1-trifluoro-2,4-pentanedione in 200 mL of ethanol at ambient temperature with stirring. The mixture was heated to reflux with stirring for 18 hours and was then allowed to cool. The volatile components were removed by evaporation under reduced pressure and the residue obtained was taken up in 150 mL, of dichloromethane. The resulting solution was washed twice with 100 mL portions of water, dried over magnesium sulfate, filtered, and concentrated by evaporation under reduced pressure to obtain 19.1 g (66 percent of theory) of the title compound as an amber oil

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. stirringwith stirring for 18 hours
  4. temperatureto cool
  5. customThe volatile components were removed by evaporation under reduced pressure
  6. customthe residue obtained
  7. washThe resulting solution was washed twice with 100 mL portions of water
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-9c4d449a241b4a029ed0e7b97708c0f9
Source dataset
uspto-grants-1998_06
Patent number
US05763359

Reaction notes

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