HCID 73033826, compound → Fipronil sulfide

HRID 2253299Notes

Reaction equation

HRID 2253299 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([Cl:12])[C:3]=1[NH:13][N:14]=[C:15]([C:24]#[N:25])[CH:16]([C:22]#[N:23])[S:17][C:18]([F:21])([F:20])[F:19]>[Cu](Cl)Cl.ClC1C=CC=CC=1>[NH2:23][C:22]1[N:13]([C:3]2[C:4]([Cl:12])=[CH:5][C:6]([C:8]([F:9])([F:11])[F:10])=[CH:7][C:2]=2[Cl:1])[N:14]=[C:15]([C:24]#[N:25])[C:16]=1[S:17][C:18]([F:19])([F:20])[F:21]

Participants

4

Reactant 1

HCID 73033826HCID 73033826, compound

Product 1

HCID 9953940Fipronil sulfideYield 73%

Reagents, catalysts & solvents 2

HCID 24014Cupric ChlorideCatalystHCID 7964ChlorobenzeneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 1-(2,6-dichloro-4-trifluoromethylphenylhydrazono) 1,2-dicyano-2-trifluoromethylthio ethane (144 mg; 0.34 mmol), prepared according to Example 3, copper (II) chloride (97 mg; 0.71 mmol), and 4 ml of chlorobezene was stirred for 4 hours at 100° C. The solvent was then evaporated under vacuum. The residue was dissolved in CH2CL2 and the solution was washed by an aqueous solution of 1% ammonia in water. The product was dried over sodium sulphate, and solvent was evaporated under reduced pressure. Purification by flash chromatography on silica gel and crystallization from dichloromethane/hexane gave a white solid (105 mg; 73% yield). The product was then recrystallized in a hexane/toluene mixture to provide a light brown powder (93 mg; 65% yield), melting point 163° C. A second recrystallization provided a white powder of the title product with a melting point 165° C.

Workup

  1. customprepared
  2. customThe solvent was then evaporated under vacuum
  3. dissolutionThe residue was dissolved in CH2CL2
  4. washthe solution was washed by an aqueous solution of 1% ammonia in water
  5. dry with materialThe product was dried over sodium sulphate, and solvent
  6. customwas evaporated under reduced pressure
  7. customPurification by flash chromatography
  8. customon silica gel and crystallization from dichloromethane/hexane
  9. customgave a white solid (105 mg; 73% yield)
  10. customThe product was then recrystallized in a hexane/toluene mixture
  11. customto provide a light brown powder (93 mg; 65% yield), melting point 163° C
  12. customA second recrystallization

Sources & evidence

ORD record
ord-96cd5a477b2a4823b1a4b9263d3bb262
Source dataset
uspto-grants-2008_01
Patent number
US07323574B2

Reaction notes

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