Sodium Thiosulfate → 2-Chloro-5-(trifluoromethyl)pyridine 1-oxide

HRID 1791901Notes

Reaction equation

HRID 1791901 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

Reactant 4

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 923422-Chloro-5-(trifluoromethyl)pyridineHCID 516892Sodium Bicarbonate

Product 1

HCID 154483422-Chloro-5-(trifluoromethyl)pyridine 1-oxideYield 11.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

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

  1. stirringafter stirring
  2. extractionthe mixture was extracted with chloroform
  3. washThe extract was washed successively with saturated aqueous sodium hydrogencarbonate solution and brine
  4. customdried
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-d420f37c18ae4fd8aae271345f20a892
Source dataset
uspto-grants-2006_07
Patent number
US07074794B2

Reaction notes

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