Sodium Thiosulfate → 3-ethylsulfonyl-N-(5-trifluoromethylpyridin-2-yl)picolinamide

HRID 713639Notes

Reaction equation

HRID 713639 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:33])([F:32])[F:31])=[CH:26][N:25]=2)=[O:22])=[N:17][CH:18]=[CH:19][CH:20]=1)C.C(=O)(O)[O-].[Na+].[S:39]([O-:43])([O-])(=[O:41])=S.[Na+].[Na+]>C(Cl)(Cl)Cl>[CH2:2]([S:39]([C:15]1[C:16]([C:21]([NH:23][C:24]2[CH:29]=[CH:28][C:27]([C:30]([F:32])([F:33])[F:31])=[CH:26][N:25]=2)=[O:22])=[N:17][CH:18]=[CH:19][CH:20]=1)(=[O:43])=[O:41])[CH3:3]

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 1182059283-ethylsulfanyl-N-(5-trifluoromethylpyridin-2-yl)picolinamide

Product 1

HCID 727376453-ethylsulfonyl-N-(5-trifluoromethylpyridin-2-yl)picolinamide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

0.30 g of m-chloroperbenzoic acid (purity of 68%) was added to a mixture of 0.20 g of 3-ethylsulfanyl-N-(5-trifluoromethylpyridin-2-yl)picolinamide (Compound of Present Invention 2) and 3 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 concentrated under reduced pressure to obtain 0.11 g of 3-ethylsulfonyl-N-(5-trifluoromethylpyridin-2-yl)picolinamide (hereinafter, referred to as Compound of Present Invention 3).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-57b2afa2ddd14e04909b061f50374065
Source dataset
uspto-grants-2015_11
Patent number
US09185910B2

Reaction notes

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