Sodium Thiosulfate → HCID 118113312, compound

HRID 713673Notes

Reaction equation

HRID 713673 reaction equation
Cl[C:2]1C=CC=C(C(OO)=O)[CH:3]=1.[Cl:12][C:13]1[CH:14]=[C:15](SCC)[C:16]([C:19]([N:21]([CH3:33])[C:22]2[CH:27]=[CH:26][C:25]([S:28][C:29]([F:32])([F:31])[F:30])=[CH:24][CH:23]=2)=[O:20])=[N:17][CH:18]=1.C(=O)(O)[O-].[Na+].[S:42]([O-:46])([O-])(=[O:44])=S.[Na+].[Na+]>C(Cl)(Cl)Cl>[Cl:12][C:13]1[CH:14]=[C:15]([S:42]([CH2:2][CH3:3])(=[O:46])=[O:44])[C:16]([C:19]([N:21]([CH3:33])[C:22]2[CH:23]=[CH:24][C:25]([S:28][C:29]([F:31])([F:30])[F:32])=[CH:26][CH:27]=2)=[O:20])=[N:17][CH:18]=1

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 118113402HCID 118113402, compound

Product 1

HCID 118113312HCID 118113312, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

10.2 g of m-chloroperbenzoic acid (purity of 68%) was added to a mixture of 9.07 g of 5-chloro-3-ethylsulfanyl-N-methyl-N-(4-trifluoromethylsulfanylphenyl)picolinamide (Compound of Present Invention 158) and 223 ml of chloroform under ice cooling, and the mixture was stirred at room temperature for 5 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 7.0 g of 5-chloro-3-ethylsulfonyl-N-methyl-N-(4-trifluoromethylsulfanylphenyl)picolinamide (hereinafter, referred to as Compound of Present Invention 118) and 2.04 g of 5-chloro-3-ethylsulfonyl-N-methyl-N-(4-trifluoromethylsulfinylphenyl)picolinamide (hereinafter, referred to as Compound of Present Invention 117).

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-52914ed4da3045ffbc801fabb03af06a
Source dataset
uspto-grants-2015_11
Patent number
US09185910B2

Reaction notes

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