Hydrogen Peroxide → HCID 178510672, Verbindung

HRID 573402

Reaktionsgleichung

Reaktionsgleichung von HRID 573402
[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)CCl.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]

Komponenten

6

Edukt 3

HCID 784Hydrogen PeroxideHCID 1118Sulfuric AcidHCID 9953940Fipronil sulfide

Produkt 1

HCID 178510672HCID 178510672, VerbindungAusbeute 74,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 111,2-DichloroethaneLösungsmittel2×HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
13.5 °C

Versuchsvorschrift

1.5 liter of ethylene 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 then 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 over a period of 3.0 to 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 10-20° C. over a period of 2.0 hours. To this mass, 1500 ml of ethylene dichloride was added and the mixture was heated to 60° C. in order to separate the aqueous and organic layers. The obtained organic phase was washed with water & then with 5% NaHCO3 solution followed by water wash, till a neutral pH was obtained. The crude yield of fipronil after removal of solvent was 425.0 gms. The crude fipronil was crystallized from same solvent after partial evaporation to yield 325 gms of crystalline fipronil with 94.0% purity.

Aufarbeitung

  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. in order
  5. customto separate the aqueous and organic layers
  6. washThe obtained organic phase was washed with water
  7. washwash, till a neutral pH
  8. customwas obtained
  9. customThe crude yield of fipronil after removal of solvent
  10. customThe crude fipronil was crystallized from same solvent
  11. customafter partial evaporation

Quellen und Nachweise

ORD-Eintrag
ord-3b92c559105a4e73a0c126c59e1d6765
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09029564B2

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