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

HRID 2232178Notes

Reaction equation

HRID 2232178 reaction equation
C(OC(=O)C)(=O)C.[N+:8]([O-:11])(O)=[O:9].[C:12]([NH:15][C:16]1[N:20]([C:21]2[C:26]([F:27])=[C:25]([F:28])[C:24]([C:29]([F:32])([F:31])[F:30])=[C:23]([F:33])[C:22]=2[F:34])[N:19]=[CH:18][CH:17]=1)(=[O:14])[CH3:13].O>C(O)(=O)C>[C:12]([NH:15][C:16]1[N:20]([C:21]2[C:22]([F:34])=[C:23]([F:33])[C:24]([C:29]([F:32])([F:31])[F:30])=[C:25]([F:28])[C:26]=2[F:27])[N:19]=[CH:18][C:17]=1[N+:8]([O-:11])=[O:9])(=[O:14])[CH3:13]

Participants

6

Reactant 4

HCID 944Nitric AcidHCID 962WaterHCID 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 94%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

12.5 ml (0.13 mol) of acetic anhydride and 4.5 ml (0.105 mol) of 98 percent strength nitric acid are added in succession to 34.1 g (0.10 mol) of 5-acetamido-1-(2,3,5,6-tetrafluoro-4-trifluoromethyl-phenyl)-pyrazole in 85 ml of glacial acetic acid at about 15° C. The temperature is allowed to rise slowly to 25° C. and the mixture is subsequently stirred for 4 hours. The reaction solution is then poured onto 250 ml of water. The precipitate is filtered off, washed neutral and dried in vacuo. 36.3 g (94% of theory) of 5-acetamido-4-nitro-1-(2,3,5,6-tetrafluoro-4-trifluoromethyl-phenyl)-pyrazole of melting point 138° C.-140° C. are obtained.

Workup

  1. customto rise slowly to 25° C.
  2. filtrationThe precipitate is filtered off
  3. washwashed neutral
  4. customdried in vacuo

Sources & evidence

ORD record
ord-33ad7e9a673647b9bf7c5b638b6aa6af
Source dataset
uspto-grants-1988_11
Patent number
US04787930

Reaction notes

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