Nitric Acid → 1-(2,3,5,6-Tetrafluoro-4-trifluoromethyl phenyl)-5-methylcarbonylamino-4-nitropyrazole

HRID 1680962Notes

Reaction equation

HRID 1680962 reaction equation
[F:1][C:2]1[C:7]([F:8])=[C:6]([C:9]([F:12])([F:11])[F:10])[C:5]([F:13])=[C:4]([F:14])[C:3]=1[N:15]1[C:19]([NH:20][C:21]([CH3:23])=[O:22])=[CH:18][CH:17]=[N:16]1.C(OC(=O)C)(=O)C.[N+:31]([O-])([OH:33])=[O:32]>C(O)(=O)C>[F:1][C:2]1[C:7]([F:8])=[C:6]([C:9]([F:12])([F:10])[F:11])[C:5]([F:13])=[C:4]([F:14])[C:3]=1[N:15]1[C:19]([NH:20][C:21]([CH3:23])=[O:22])=[C:18]([N+:31]([O-:33])=[O:32])[CH:17]=[N:16]1

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 7918Acetic AnhydrideHCID 139337111-(2,3,5,6-Tetrafluoro-4-trifluoromethylphenyl)-5-methylcarbonylaminopyrazole

Product 1

HCID 139337121-(2,3,5,6-Tetrafluoro-4-trifluoromethyl phenyl)-5-methylcarbonylamino-4-nitropyrazoleYield 63.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A stirred solution of 7.86 grams (0.0230 mole) of 1-(2,3,5,6-tetrafluoro-4-trifluoromethylphenyl)-5-methylcarbonylaminopyrazole in 20 mL of glacial acetic acid was cooled in an ice-water bath. Acetic anhydride (2.9 mL, 0.031 mole) was added dropwise, and the mixture was stirred briefly. Concentrated nitric acid (1.05 mL, 0.0245 mole) was added dropwise, and the reaction mixture was allowed to warm to room temperature and was stirred for four hours. The mixture was poured into 60 mL of ice-water and stirred, forming a granular yellow solid. This solid was collected by filtration and washed with water. The solid was purified by recrystallization from ethanol and water to yield 5.63 grams of 1-(2,3,5,6-tetrafluoro-4-trifluoromethylphenyl) -5-methylcarbonylamino-4-nitropyrazole, m.p. 136.5-138.5° C. The nmr spectrum was consistent with the proposed structure.

Workup

  1. stirringwas stirred for four hours
  2. stirringstirred
  3. customforming a granular yellow solid
  4. filtrationThis solid was collected by filtration
  5. washwashed with water
  6. customThe solid was purified by recrystallization from ethanol and water

Sources & evidence

ORD record
ord-5f34afc7d74d4d6d8766950446d1ae19
Source dataset
uspto-grants-1992_12
Patent number
US05167691

Reaction notes

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