Hydrogen Peroxide → HCID 178510672, compound

HRID 573403

Reaction equation

HRID 573403 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]#[N:20])[C:3]=1[S:21][C:22]([F:25])([F:24])[F:23].OO.[OH:28]S(O)(=O)=O>C(Cl)Cl.O>[CH:11]1[C:10]([C:14]([F:15])([F:16])[F:17])=[CH:9][C:8]([Cl:18])=[C:7]([N:6]2[N:5]=[C:4]([C:19]#[N:20])[C:3]([S+:21]([O-:28])[C:22]([F:25])([F:24])[F:23])=[C:2]2[NH2:1])[C:12]=1[Cl:13]

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 1118Sulfuric AcidHCID 9953940Fipronil sulfide

Product 1

HCID 178510672HCID 178510672, compoundYield 74.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
13.5 °C

Procedure

1.5 liter of methylene dichloride & 421.0 gms of 5-amino-3-cyano-1-(2,6-dichloro-4-trifluromethylphenyl)-4-trifluromethylthio pyrazole was charged in a reactor flask with overhead stirring & condenser system. This mass was cooled to 12-15° C. and 68.0 gms of H2O2 (50.0% w/w) & 500.0 gms of H2SO4 (90.0% w/w) were simultaneously added to the mass over a period of 3.0-4.0 hours. The reaction temperature was then raised to 28-30° C. & maintained for about 2.0 hours. The reaction mass obtained thereafter was slowly added into 1700 ml of chilled water at a temperature of about 10-20° C. over a period of 2.0 hours. To this mass, 1500 ml of methylene dichloride was added and the mixture was heated to 60° C. to separate the aqueous and organic layers. The organic phase was washed with water & then with 5% NaHCO3 solution, followed by water wash, till a neutral pH was obtained. The crude yield obtained was 425.0 gms. The obtained crude fipronil was then crystallized from same solvent after partial evaporation to yield crystalline Fipronil (325 gms) with 94.0% purity.

Workup

  1. temperatureThe reaction temperature was then raised to 28-30° C.
  2. temperaturemaintained for about 2.0 hours
  3. customThe reaction mass obtained
  4. temperaturethe mixture was heated to 60° C.
  5. customto separate the aqueous and organic layers
  6. washThe organic phase was washed with water
  7. washwash, till a neutral pH
  8. customwas obtained
  9. customThe crude yield
  10. customobtained
  11. customThe obtained crude fipronil
  12. customwas then crystallized from same solvent
  13. customafter partial evaporation

Sources & evidence

ORD record
ord-0749790f9e9148f4bd0f9169f42554f4
Source dataset
uspto-grants-2015_05
Patent number
US09029564B2

Linked notes

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