Nitric Acid → HCID 22618355, compound

HRID 1078456Notes

Reaction equation

HRID 1078456 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([C:14]([F:17])([F:16])[F:15])=[CH:9][C:8]=2[Cl:18])[N:5]=[C:4]([C:19]([F:22])([F:21])[F:20])[CH:3]=1.[N+:23]([O-])([OH:25])=[O:24]>S(=O)(=O)(O)O.C(OCC)(=O)C.CCCCCC>[NH2:1][C:2]1[N:6]([C:7]2[C:8]([Cl:18])=[CH:9][C:10]([C:14]([F:15])([F:16])[F:17])=[CH:11][C:12]=2[Cl:13])[N:5]=[C:4]([C:19]([F:22])([F:21])[F:20])[C:3]=1[N+:23]([O-:25])=[O:24]

Participants

6

Reactant 2

HCID 944Nitric AcidHCID 22618376HCID 22618376, compound

Product 1

HCID 22618355HCID 22618355, compound

Reagents, catalysts & solvents 3

HCID 1118Sulfuric AcidSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 5-amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-3-trifluoromethylpyrazole (3.0 g) in concentrated sulphuric acid (10 ml) at 0° C. was treated with fuming nitric acid (9 ml) during 15 minutes, keeping the temperature at 5°-15° C. After 30 minutes the mixture was poured onto excess ice, and the precipitated solid was filtered off and dissolved in ethyl acetate. After drying over anhydrous magnesium sulphate, filtration, and evaporation in vacuo a brown oil was obtained. This oil was dissolved in the minimum of ethyl acetate and diluted with hexane. A pale yellow solid crystallized and this was discarded. The filtrate was evaporated in vacuo to give a solid which was recrystallized from toluene-hexane to furnish a yellow solid. One further recrystallization from the same solvent pair gave 5-amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-nitro-3-trifluoromethylpyrazole as white crystals, m.p. 214°-215° C.

Workup

  1. customat 5°-15° C
  2. additionAfter 30 minutes the mixture was poured onto excess ice
  3. filtrationthe precipitated solid was filtered off
  4. dissolutiondissolved in ethyl acetate
  5. dry with materialAfter drying over anhydrous magnesium sulphate, filtration, and evaporation in vacuo a brown oil
  6. customwas obtained
  7. customA pale yellow solid crystallized
  8. customThe filtrate was evaporated in vacuo
  9. customto give a solid which
  10. customwas recrystallized from toluene-hexane
  11. customto furnish a yellow solid
  12. customOne further recrystallization from the same solvent pair

Sources & evidence

ORD record
ord-c49a5d1dc7c448e0ac2d0a23a29669a6
Source dataset
uspto-grants-1996_08
Patent number
US05547974

Reaction notes

Loading…