Hydrogen Peroxide → HCID 11079417, compound

HRID 1871871Notes

Reaction equation

HRID 1871871 reaction equation
OO.[N+:3]([C:6]1[CH:7]=[N:8][N:9]([C:16]2[C:21]([Cl:22])=[CH:20][C:19]([C:23]([F:26])([F:25])[F:24])=[CH:18][N:17]=2)[C:10]=1[NH:11][C:12](=[O:15])[CH2:13][CH3:14])([O-:5])=[O:4].FC(F)(F)C(O)=[O:30]>O>[N+:3]([C:6]1[CH:7]=[N:8][N:9]([C:16]2[C:21]([Cl:22])=[CH:20][C:19]([C:23]([F:26])([F:25])[F:24])=[CH:18][N+:17]=2[O-:30])[C:10]=1[NH:11][C:12](=[O:15])[CH2:13][CH3:14])([O-:5])=[O:4]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 6422Trifluoroacetic acidHCID 10872190HCID 10872190, compound

Product 1

HCID 11079417HCID 11079417, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2.8 g (0.0413 mol) of 50% strength hydrogen peroxide were added to a mixture of 10 g (0.0275 mol) of 4-nitro-5-propionamido-1-(3-chloro-5-trifluoromethyl-2-pyridyl)pyrazole and 100 ml of trifluoroacetic acid at 20° C. with stirring in the course of 5 minutes and it was stirred at 25° C. for 14 hours. The reaction mixture was poured onto 500 ml of water and extracted 3× with methylene chloride. The organic phase was washed with water, sodium hydrogencarbonate and saturated sodium chloride solution in succession and dried over magnesium sulfate. After concentrating under reduced pressure, stirring with ether/pentane, filtering off with suction and drying, 9.0 g (85% of theory) of 4-nitro-5-propionamido-1-(3-chloro-5-trifluoromethyl-(N-oxido)-2-pyridyl)pyrazole of m.p. 143-146° C. were obtained.

Workup

  1. stirringwas stirred at 25° C. for 14 hours
  2. extractionextracted 3× with methylene chloride
  3. washThe organic phase was washed with water, sodium hydrogencarbonate and saturated sodium chloride solution in succession
  4. dry with materialdried over magnesium sulfate
  5. concentrationAfter concentrating under reduced pressure
  6. stirringstirring with ether/pentane
  7. filtrationfiltering off with suction
  8. customdrying

Sources & evidence

ORD record
ord-cd3b61a09eff46708cd5391b8de99aa6
Source dataset
uspto-grants-2000_08
Patent number
US06107253

Reaction notes

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