Hydrogen Peroxide → HCID 178510672, compound

HRID 573406Notes

Reaction equation

HRID 573406 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].[OH:26]S(O)(=O)=O.OO.O>C(Cl)CCl>[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-:26])[C:22]([F:25])([F:24])[F:23])=[C:2]2[NH2:1])[C:12]=1[Cl:13]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 1118Sulfuric AcidHCID 9953940Fipronil sulfide

Product 1

HCID 178510672HCID 178510672, compoundYield 72.1%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
11.5 °C

Procedure

3.0 liter of ethylene dichloride solvent & 421.0 gms of 5-amino-3-cyano-1-(2,6-dichloro-4-trifluromethylphenyl)-4-trifluromethylthio pyrazole was charged into a reactor flask with overhead stirring & condenser system. This mass was cooled to a temperature of about 5-10° C. and 1000.0 gms of H2SO4 (85.0% w/w) was added over a period of 1.5 to 2.0 hours. 61.0 gms of H2O2 (50.0% w/w) was then added to the aforesaid mass over a period of 3.0 hours at 07-13° C. The reaction temperature was maintained at a temperature of about 10-13° C. for about 1.0 hours. The reaction mass obtained thereafter was slowly added into 370 ml of chilled water at a 10-25° C. over a period of 2.0 hours. This mass was treated as in above experiments to yield crystalline fipronil (315.0 gms) of 95.0-96.5% purity.

Workup

  1. additionwas added over a period of 1.5 to 2.0 hours
  2. customThe reaction mass obtained
  3. additionThis mass was treated as in above experiments

Sources & evidence

ORD record
ord-11b5fa4bda564dfe8975f04dfde0e4c0
Source dataset
uspto-grants-2015_05
Patent number
US09029564B2

Reaction notes

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