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Sodium Thiosulfate → 2-ethylsulfonyl-N-methyl-4-trifluoromethyl-N-(5-trifluoromethyl-pyridin-2-yl)-benzamide

HRID 1052929
Notes
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Reaction equation

HRID 1052929 reaction equation
Cl[C:2]1C=CC=C(C(OO)=O)[CH:3]=1.C(S[C:15]1[CH:34]=[C:33]([C:35]([F:38])([F:37])[F:36])[CH:32]=[CH:31][C:16]=1[C:17]([N:19]([CH3:30])[C:20]1[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][N:21]=1)=[O:18])C.C(=O)(O)[O-].[Na+].[S:44]([O-:48])([O-])(=[O:46])=S.[Na+].[Na+]>C(Cl)(Cl)Cl>[CH2:2]([S:44]([C:15]1[CH:34]=[C:33]([C:35]([F:38])([F:36])[F:37])[CH:32]=[CH:31][C:16]=1[C:17]([N:19]([CH3:30])[C:20]1[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][N:21]=1)=[O:18])(=[O:48])=[O:46])[CH3:3]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 729447402-ethylsulfanyl-N-methyl-4-trifluoromethyl-N-(5-trifluoromethyl-pyridin-2-yl)-benzamide

Product 1

HCID 1180351862-ethylsulfonyl-N-methyl-4-trifluoromethyl-N-(5-trifluoromethyl-pyridin-2-yl)-benzamide

Reagents, catalysts & solvents

1
HCID 6212ChloroformSolvent

Procedure

0.53 g of m-chloroperbenzoic acid (purity of 68%) was added to a mixture of 0.36 g of 2-ethylsulfanyl-N-methyl-4-trifluoromethyl-N-(5-trifluoromethyl-pyridin-2-yl)-benzamide and 3 mL of chloroform under ice cooling, and the mixture was stirred at room temperature for 3 hours. A saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium thiosulfate solution were added 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. The resulting residue was applied to a silica gel column chromatography to obtain 0.37 g of 2-ethylsulfonyl-N-methyl-4-trifluoromethyl-N-(5-trifluoromethyl-pyridin-2-yl)-benzamide (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-fd358643447c447e83e864668e31508b
Source dataset
uspto-grants-2016_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09392791B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes