Water → 4-Chloro-3-(2,6-dichloro-4-trifluoromethylphenyl)-1-methyl-5-methylsulfenylpyrazole
Reaction equation
S(Cl)([Cl:4])(=O)=O.[Cl:6][C:7]1[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=[C:9]([Cl:17])[C:8]=1[C:18]1[CH:22]=[C:21]([S:23][CH3:24])[N:20]([CH3:25])[N:19]=1.O>C(Cl)(Cl)(Cl)Cl>[Cl:4][C:22]1[C:18]([C:8]2[C:7]([Cl:6])=[CH:12][C:11]([C:13]([F:16])([F:15])[F:14])=[CH:10][C:9]=2[Cl:17])=[N:19][N:20]([CH3:25])[C:21]=1[S:23][CH3:24]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A 0.3 g quantity of sulfuryl chloride was added to 1.2 g of 3-(2,6-dichloro-4-trifluoromethylphenyl)-1-methyl-5-methylsulfenylpyrazole (compound 1) in 5 ml of anhydrous carbon tetrachloride at room temperature, followed by stirring at room temperature for 2 hours. The reaction mixture was poured into cold water, and the resulting mixture was extracted with methylene chloride. The organic layer was washed with 10% aqueous sodium hydrogen carbonate solution and with brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain a residue, which was then purified by column chromatography on silica gel (eluent: ether/hexane=1/5), giving 1.0 g of the desired compound in the form of white crystals (yield 83.3%).
Workup
- extractionthe resulting mixture was extracted with methylene chloride
- washThe organic layer was washed with 10% aqueous sodium hydrogen carbonate solution and with brine
- dry with materialdried over anhydrous magnesium sulfate
- distillationThe solvent was distilled off under reduced pressure
- customto obtain a residue, which
- customwas then purified by column chromatography on silica gel (eluent: ether/hexane=1/5)
Sources & evidence
- ORD record
- ord-f3aa01db2cb94848b07050e6bbc042b4
- Source dataset
- uspto-grants-1998_04
- Patent number
- US05739083
Reaction notes
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