Nitric Acid → HCID 14053966, compound

HRID 622288Notes

Reaction equation

HRID 622288 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[N:13]1[C:17]([O:18][CH:19]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH3:20])=[CH:16][CH:15]=[N:14]1.[N+:26]([O-])([OH:28])=[O:27].C(=O)([O-])O.[Na+]>C(OC(=O)C)(=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:10])([F:9])[F:11])[CH:5]=[C:4]([Cl:12])[C:3]=1[N:13]1[C:17]([O:18][CH:19]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH3:20])=[C:16]([N+:26]([O-:28])=[O:27])[CH:15]=[N:14]1

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 516892Sodium BicarbonateHCID 14053967HCID 14053967, compound

Product 1

HCID 14053966HCID 14053966, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

17 g (0.05 mol) of 1-(2,6-dichloro-4-trifluoromethyl-phenyl)-5-(1-ethoxycarbonyl-ethoxy)-pyrazole are dissolved in 50 ml of acetic anhydride, and 10 ml of concentrated nitric acid are added dropwise with stirring at 0°-10° C. within 15 minutes. The reaction batch is stirred for a further 1 hour at room temperature and then poured onto ice water. After neutralization of the mixture using sodium hydrogen carbonate, the organic components are extracted with methylene chloride. The methylene chloride phase is dried over sodium sulphate and concentrated in vacuo. The crude yield of oily reaction product is 17 g. After trituration with petroleum ether, 10.8 g (49% of theory) of 1-(2,6-dichloro-4-trifluoromethylphenyl)-5-(1-ethoxycarbonyl-ethoxy)-4-nitro-pyrazole are obtained in the form of oily crystals.

Workup

  1. stirringThe reaction batch is stirred for a further 1 hour at room temperature
  2. additionpoured onto ice water
  3. extractionthe organic components are extracted with methylene chloride
  4. dry with materialThe methylene chloride phase is dried over sodium sulphate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-04bad0cbe8c843b6ae102196925ad24b
Source dataset
uspto-grants-1988_09
Patent number
US04770692

Reaction notes

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