Sodium Thiosulfate → 2-Chloro-5-(trifluoromethyl)pyridine 1-oxide
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][N:3]=1.ClC1C=CC=C(C(OO)=[O:20])C=1.S([O-])([O-])(=O)=S.[Na+].[Na+].C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:9])([F:10])[F:11])=[CH:4][N+:3]=1[O-:20]Participants
6
Conditions
- Temperature
- 60 °C
Procedure
2-Chloro-5-trifluoromethylpyridine (5 g) was dissolved in chloroform (150 mL) and m-chloroperbenzoic acid (14.3 g) was added thereto. The mixture was stirred at 60° C. for 30 hr. Aqueous sodium thiosulfate solution and saturated aqueous sodium hydrogencarbonate solution were added to the reaction mixture, and after stirring, the mixture was extracted with chloroform. The extract was washed successively with saturated aqueous sodium hydrogencarbonate solution and brine, and dried. The solvent was evaporated under reduced pressure and the residue was purified by silica gel chromatography to give 2-chloro-5-trifluoromethylpyridine 1-oxide (0.64 g).
Workup
- stirringafter stirring
- extractionthe mixture was extracted with chloroform
- washThe extract was washed successively with saturated aqueous sodium hydrogencarbonate solution and brine
- customdried
- customThe solvent was evaporated under reduced pressure
- customthe residue was purified by silica gel chromatography
Sources & evidence
- ORD record
- ord-68098f7c253a457289b1409d8560964c
- Source dataset
- uspto-grants-2006_06
- Patent number
- US07060722B2
Reaction notes
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