Water → HCID 18929397, compound

HRID 1598523Notes

Reaction equation

HRID 1598523 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[C:6]([Cl:14])[C:5]=1[C:15]1[CH:19]=[C:18]([S:20][CH3:21])[NH:17][N:16]=1.[F:22][C:23](I)([F:25])[F:24].O>CN(C)C=O>[Cl:14][C:6]1[CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:9]=[C:4]([Cl:3])[C:5]=1[C:15]1[CH:19]=[C:18]([S:20][CH3:21])[N:17]([C:23]([F:25])([F:24])[F:22])[N:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 16843TrifluoroiodomethaneHCID 24758Sodium hydrideHCID 178503086HCID 178503086, compound2×

Product 1

HCID 18929397HCID 18929397, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride was added dropwise to a suspension of 0.5 g of 3-(2,6-dichloro-4-trifluoromethylphenyl)-5(methylsulfenyl)pyrazole (compound 16) in 5 ml of anhydrous N,N-dimethylformamide at 0° C., and the mixture was stirred at room temperature. An excess of trifluoromethyl iodide was introduced into the reaction mixture, and the resulting mixture was stirred for 3 hours with the reactor closed. The reaction mixture was poured into water, followed by extraction with ether, washing with brine and drying over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain a residue, which was purified by column chromatography on silica gel (eluent: chloroform/hexane=1/20), giving 0.2 g of the desired product in the form of light brown oil (yield 33.3%).

Workup

  1. stirringthe resulting mixture was stirred for 3 hours with the reactor
  2. customclosed
  3. extractionfollowed by extraction with ether
  4. washwashing with brine
  5. dry with materialdrying over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customto obtain a residue, which
  8. customwas purified by column chromatography on silica gel (eluent: chloroform/hexane=1/20)

Sources & evidence

ORD record
ord-08e0aa15fe0d4faca37fc8e68544b81c
Source dataset
uspto-grants-1998_04
Patent number
US05739083

Reaction notes

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