Nitric Acid → HCID 19080754, compound

HRID 963146Notes

Reaction equation

HRID 963146 reaction equation
[CH2:1]([N:3]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([C:10]([F:13])([F:12])[F:11])=[N:4]1)[CH3:2].S(=O)(=O)(O)O.[N+:19]([O-])([OH:21])=[O:20]>O.[OH-].[Na+]>[CH2:1]([N:3]1[C:7]([O:8][CH3:9])=[C:6]([N+:19]([O-:21])=[O:20])[C:5]([C:10]([F:11])([F:13])[F:12])=[N:4]1)[CH3:2]

Participants

6

Reactant 3

HCID 944Nitric Acid2×HCID 1118Sulfuric AcidHCID 19080777HCID 19080777, compound

Product 1

HCID 19080754HCID 19080754, compoundYield 66,050.797%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

1-Ethyl-5-methoxy-3-(trifluoromethyl)pyrazole (15.2 g, 0.0785 mmol) was added dropwise with stirring and cooling at about 0° C. to 150 mL of concentrated sulfuric acid and then 10.5 mL of 70 percent nitric acid (0.235 mmol) was added, also dropwise with stirring at about 0° C. The mixture was then allowed to warm to ambient temperature and stir overnight. An aliquot was removed, neutralized to a pH of about 11, extracted with dichloromethane, and analyzed by gas chromatography. Since there was still some starting material present another about 0.8 mmol of concentrated nitric acid was added with stirring and the mixture was allowed to react for 5 hours. Analysis of an aliquot as before did not reveal any remaining starting material so the mixture was poured slowly into 500 g of ice. The mixture was stirred for 15 min and was then extracted with dichloromethane (4×200 mL). The extracts were combined to obtain an acidic blue-green organic mixture. This was diluted with 100 mL of water and neutralized with 50 percent aqueous sodium hydroxide. The mixture, which turned yellow-orange, was separated into phases and the organic layer was dried over magnesium sulfate, filtered, and concentrated under reduced pressure to obtain 12.4 g of the title compound as a yellow oil.

Workup

  1. stirringalso dropwise with stirring at about 0° C
  2. stirringstir overnight
  3. customAn aliquot was removed
  4. extractionextracted with dichloromethane
  5. additionwas added
  6. stirringwith stirring
  7. customto react for 5 hours
  8. stirringThe mixture was stirred for 15 min
  9. extractionwas then extracted with dichloromethane (4×200 mL)
  10. customto obtain an acidic blue-green organic mixture
  11. customwas separated into phases
  12. dry with materialthe organic layer was dried over magnesium sulfate
  13. filtrationfiltered
  14. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-bc54f90ee9454a868c14c8f5b0ca1566
Source dataset
uspto-grants-1998_06
Patent number
US05763359

Reaction notes

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