Sodium Thiosulfate → 3-ethylsulfonyl-N-(5-pentafluoroethylpyridin-2-yl)picolinamide
Reaction equation
Cl[C:2]1C=CC=C(C(OO)=O)[CH:3]=1.C(S[C:15]1[C:16]([C:21]([NH:23][C:24]2[CH:29]=[CH:28][C:27]([C:30]([F:36])([F:35])[C:31]([F:34])([F:33])[F:32])=[CH:26][N:25]=2)=[O:22])=[N:17][CH:18]=[CH:19][CH:20]=1)C.C(=O)(O)[O-].[Na+].[S:42]([O-:46])([O-])(=[O:44])=S.[Na+].[Na+]>C(Cl)(Cl)Cl>[CH2:2]([S:42]([C:15]1[C:16]([C:21]([NH:23][C:24]2[CH:29]=[CH:28][C:27]([C:30]([F:35])([F:36])[C:31]([F:32])([F:34])[F:33])=[CH:26][N:25]=2)=[O:22])=[N:17][CH:18]=[CH:19][CH:20]=1)(=[O:46])=[O:44])[CH3:3]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
0.25 g of m-chloroperbenzoic acid (purity of 68%) was added to a mixture of 0.18 g of 3-ethylsulfanyl-N-(5-pentafluoroethylpyridin-2-yl)picolinamide (Compound of Present Invention 46) and 5 mL of chloroform under ice cooling, and the mixture was stirred at room temperature for 2 hours. A saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium thiosulfate solution were poured to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure, and the resulting residue was applied to a silica gel column chromatography to obtain 0.15 g of 3-ethylsulfonyl-N-(5-pentafluoroethylpyridin-2-yl)picolinamide (hereinafter, referred to as Compound of Present Invention 47).
Workup
- extractionthe mixture was extracted with ethyl acetate
- dry with materialThe organic layer was dried over anhydrous sodium sulfate
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-68db8669eadc4073b4bb8cccd26f6db9
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09185910B2
Reaction notes
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