Sodium Thiosulfate → 2-(2-ethylsulfonyl-4-trifluoromethylsulfanylphenyl)3-methyl-6-trifluoromethylsulfanyl-3H-imidazo[4,5-b]pyridine

HRID 1750060Notes

Reaction equation

HRID 1750060 reaction equation
Cl[C:2]1C=C(C=C[CH:11]=1)C(OO)=O.C(S[C:15]1[CH:20]=[C:19]([S:21][C:22]([F:25])([F:24])[F:23])[CH:18]=[CH:17][C:16]=1[C:26]1[N:39]([CH3:40])[C:29]2=[N:30][CH:31]=[C:32]([S:34][C:35]([F:38])([F:37])[F:36])[CH:33]=[C:28]2[N:27]=1)C.C(=O)(O)[O-].[Na+].[S:46]([O-:50])([O-])(=[O:48])=S.[Na+].[Na+]>C(Cl)(Cl)Cl>[CH2:2]([S:46]([C:15]1[CH:20]=[C:19]([S:21][C:22]([F:23])([F:24])[F:25])[CH:18]=[CH:17][C:16]=1[C:26]1[N:39]([CH3:40])[C:29]2=[N:30][CH:31]=[C:32]([S:34][C:35]([F:38])([F:36])[F:37])[CH:33]=[C:28]2[N:27]=1)(=[O:50])=[O:48])[CH3:11]

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 1180356112-(2-ethylsulfanyl-4-trifluoromethylsulfanylphenyl)3-methyl-6-trifluoromethylsulfanyl-3H-imidazo[4,5-b]pyridine

Product 1

HCID 1180356542-(2-ethylsulfonyl-4-trifluoromethylsulfanylphenyl)3-methyl-6-trifluoromethylsulfanyl-3H-imidazo[4,5-b]pyridine

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

0.20 g of 3-chloroperoxybenzoic acid (purity of 65% or more) was added to a mixture of 0.20 g of 2-(2-ethylsulfanyl-4-trifluoromethylsulfanylphenyl)3-methyl-6-trifluoromethylsulfanyl-3H-imidazo[4,5-b]pyridine and 3 ml of chloroform under ice cooling, and then the mixture was stirred under ice cooling for 2 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 then concentrated under reduced pressure. The resulting residue was applied to a silica gel column chromatography to obtain 0.22 g of 2-(2-ethylsulfonyl-4-trifluoromethylsulfanylphenyl)3-methyl-6-trifluoromethylsulfanyl-3H-imidazo[4,5-b]pyridine (hereinafter, referred to as Compound 9).

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-adb518dacb524663a330f3dee3aebe44
Source dataset
uspto-grants-2015_10
Patent number
US09156838B2

Reaction notes

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