Nitric Acid → HCID 19993698, compound

HRID 345122Notes

Reaction equation

HRID 345122 reaction equation
[N+:1]([O-:4])(O)=[O:2].[C:5]([C:7]1[C:11]([O:12][CH:13]([F:15])[F:14])=[CH:10][N:9]([C:16]2[C:21]([Cl:22])=[CH:20][C:19]([C:23]([F:26])([F:25])[F:24])=[CH:18][C:17]=2[Cl:27])[N:8]=1)#[N:6]>S(=O)(=O)(O)O>[C:5]([C:7]1[C:11]([O:12][CH:13]([F:15])[F:14])=[C:10]([N+:1]([O-:4])=[O:2])[N:9]([C:16]2[C:21]([Cl:22])=[CH:20][C:19]([C:23]([F:24])([F:25])[F:26])=[CH:18][C:17]=2[Cl:27])[N:8]=1)#[N:6]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 19993715HCID 19993715, compound

Product 1

HCID 19993698HCID 19993698, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

Fuming nitric acid (5 ml) was added to an ice-cooled solution of 3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-difluoromethoxypyrazole (1.5g) in concentrated sulfuric acid (20 ml). The mixture was stirred at room temperature for 3 hours then poured into ice/water and extracted into dichloromethane (3×50 ml). The combined dichloromethane extracts were washed with water (30 ml), filtered through phase-separation paper and evaporated in vacuo. The resultant gum was purified by dry-column chromatography (eluant ether:hexane 1:3) t give 3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-difluoromethoxy-5-nitropyrazole (0.3g) as a yellow solid, m.p. 72.5°-74° C.

Workup

  1. extractionextracted into dichloromethane (3×50 ml)
  2. washThe combined dichloromethane extracts were washed with water (30 ml)
  3. filtrationfiltered through phase-separation paper
  4. customevaporated in vacuo
  5. customThe resultant gum was purified by dry-column chromatography (eluant ether:hexane 1:3)

Sources & evidence

ORD record
ord-4bbab2edc0984828bc6b13acb19c0f19
Source dataset
uspto-grants-1991_10
Patent number
US05055482

Reaction notes

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