Nitric Acid → HCID 18929413, compound

HRID 1598517Notes

Reaction equation

HRID 1598517 reaction equation
[N+:1]([O-:4])(O)=[O:2].S(=O)(=O)(O)O.[NH2:10][C:11]1[N:15]([CH3:16])[N:14]=[C:13]([C:17]2[C:22]([Cl:23])=[CH:21][C:20]([C:24]([F:27])([F:26])[F:25])=[CH:19][C:18]=2[Cl:28])[CH:12]=1>O>[NH2:10][C:11]1[N:15]([CH3:16])[N:14]=[C:13]([C:17]2[C:22]([Cl:23])=[CH:21][C:20]([C:24]([F:25])([F:27])[F:26])=[CH:19][C:18]=2[Cl:28])[C:12]=1[N+:1]([O-:4])=[O:2]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 18929404HCID 18929404, compound

Product 1

HCID 18929413HCID 18929413, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 2.8 g of concentrated nitric acid was added dropwise 3.7 g of concentrated sulfuric acid at room temperature, followed by stirring for 10 minutes to obtain a mixed acid solution. A 0.5 g quantity of 5-amino-3-(2,6-dichloro-4-trifluoromethylphenyl)-1-methylpyrazole (13) was added in small portions to the solution at 60° C., and the mixture was stirred at the same temperature for 1 hour. The reaction mixture was added to water, the resulting mixture was extracted with ether, and the aqueous layer was made weakly alkaline with a saturated sodium carbonate aqueous solution and then extracted with ethyl acetate, followed by washing with brine and drying over anhydrous magnesium sulfate. Removal of the solvent gave 0.2 g of the desired compound in the form of orange crystals (yield 35.1%), m.p. 107°-108° C.

Workup

  1. customto obtain a mixed acid solution
  2. stirringthe mixture was stirred at the same temperature for 1 hour
  3. extractionthe resulting mixture was extracted with ether
  4. extractionextracted with ethyl acetate
  5. washby washing with brine
  6. dry with materialdrying over anhydrous magnesium sulfate
  7. customRemoval of the solvent

Sources & evidence

ORD record
ord-b431d3ccf87e4914bde1bbd2e2bb5ddf
Source dataset
uspto-grants-1998_04
Patent number
US05739083

Reaction notes

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