1,2-Dichloroethane → HCID 178510672, Verbindung

HRID 573404

Reaktionsgleichung

Reaktionsgleichung von HRID 573404
C(Cl)CCl.[NH2:5][C:6]1[N:10]([C:11]2[C:16]([Cl:17])=[CH:15][C:14]([C:18]([F:21])([F:20])[F:19])=[CH:13][C:12]=2[Cl:22])[N:9]=[C:8]([C:23]#[N:24])[C:7]=1[S:25][C:26]([F:29])([F:28])[F:27].OO.[OH:32]S(O)(=O)=O>O>[CH:15]1[C:14]([C:18]([F:19])([F:20])[F:21])=[CH:13][C:12]([Cl:22])=[C:11]([N:10]2[N:9]=[C:8]([C:23]#[N:24])[C:7]([S+:25]([O-:32])[C:26]([F:29])([F:28])[F:27])=[C:6]2[NH2:5])[C:16]=1[Cl:17]

Komponenten

6

Edukt 4

HCID 111,2-DichloroethaneHCID 784Hydrogen PeroxideHCID 1118Sulfuric AcidHCID 9953940Fipronil sulfide

Produkt 1

HCID 178510672HCID 178510672, VerbindungAusbeute 80,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
7.5 °C

Versuchsvorschrift

3.0 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 cooled to a temperature of about 5-10° C. 95.0 gms of H2O2 (50.0% w/w) & 2000.0 gms H2SO4 (85.0% w/w) were simultaneously added over a period of 3-4 hours. The reaction temperature was maintained at 12-15° C. for about 2.0 hours with monitoring of reaction conversion. The reaction mass obtained thereafter was slowly added into 800 ml of chilled water at a temperature of about 10-20° C. over a period of 2.0 hours. This mass was heated to a temperature of about 60-65° C. to separate the aqueous and organic layers. The organic phase was washed with water & then with 5% NaHCO3, followed by water wash, till a neutral pH was obtained. The crude yield of fipronil after removal of solvent was 435.0 gms. The crude fipronil was then crystallized to yield 350.0 gms of fipronil with 95.50% purity.

Aufarbeitung

  1. temperatureThe reaction temperature was maintained at 12-15° C. for about 2.0 hours with monitoring of reaction conversion
  2. customThe reaction mass obtained
  3. temperatureThis mass was heated to a temperature of about 60-65° C.
  4. customto separate the aqueous and organic layers
  5. washThe organic phase was washed with water
  6. washwash, till a neutral pH
  7. customwas obtained
  8. customThe crude yield of fipronil after removal of solvent
  9. customThe crude fipronil was then crystallized

Quellen und Nachweise

ORD-Eintrag
ord-ed4ad0baa7574e66a9fb9ab6aca5fd11
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09029564B2

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