Nitric Acid → HCID 18425034, compound

HRID 1280321Notes

Reaction equation

HRID 1280321 reaction equation
[Cl:1][C:2]1[C:3]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[C:14]=2[Cl:20])=[N:4][N:5]([CH3:11])[C:6]=1[O:7][CH:8]([F:10])[F:9].[N+:21]([O-])([OH:23])=[O:22]>>[Cl:1][C:2]1[CH:3]([CH2:12][C:13]2[CH:18]=[C:17]([N+:21]([O-:23])=[O:22])[CH:16]=[C:15]([Cl:19])[C:14]=2[Cl:20])[NH:4][N:5]([CH3:11])[C:6]=1[O:7][CH:8]([F:10])[F:9]

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 11824049HCID 11824049, compound

Product 1

HCID 18425034HCID 18425034, compound

Procedure

At −10° C., 6.6 g (19 mmol) of 4-chloro-3-(2,3-dichlorobenzyl)-5-difluoromethoxy-methyl-1H-pyrazole were dissolved in 100 ml of nitric acid. After 30 minutes, the mixture was warmed to 0—5° C. and 200 g of ice were added. The product of value was then extracted with dichloromethane. The organic phase was washed with saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution, dried over magnesium sulfate and finally concentrated. The product of value was purified by MPLC over silica gel (eluent: cyclohexane/ethyl acetate=4:1).

Workup

  1. temperaturethe mixture was warmed to 0—5° C.
  2. extractionThe product of value was then extracted with dichloromethane
  3. washThe organic phase was washed with saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. concentrationfinally concentrated
  6. customThe product of value was purified by MPLC over silica gel (eluent: cyclohexane/ethyl acetate=4:1)

Sources & evidence

ORD record
ord-c63e681a0b874bb5935fa8fbe060a407
Source dataset
uspto-grants-2002_09
Patent number
US06451734B1

Reaction notes

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