Sodium Thiosulfate → HCID 86708213, compound

HRID 533623Notes

Reaction equation

HRID 533623 reaction equation
[Cl:1][C:2]1[C:3]([S:22][CH2:23][CH3:24])=[C:4]([C:8]2[N:20]([CH3:21])[C:11]3=[N:12][CH:13]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:15]=[C:10]3[N:9]=2)[CH:5]=[CH:6][CH:7]=1.ClC1C=CC=C(C(OO)=[O:33])C=1.C(=O)([O-])O.[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)(Cl)Cl>[Cl:1][C:2]1[C:3]([S:22]([CH2:23][CH3:24])=[O:33])=[C:4]([C:8]2[N:20]([CH3:21])[C:11]3=[N:12][CH:13]=[C:14]([C:16]([F:18])([F:19])[F:17])[CH:15]=[C:10]3[N:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 86708214HCID 86708214, compound

Product 1

HCID 86708213HCID 86708213, compoundYield 89.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a mixture of 2-(3-chloro-2-ethylsulfanylphenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (0.72 g) and chloroform (10 ml), 3-chloroperbenzoic acid (purity: 69-75%, 0.66 g) was added under ice-cooling, and then heated to room temperature, and stirred for 20 minutes. Into the reaction mixture, saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium thiosulfate solution were poured, and extracted with chloroform 2 times. The combined organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 0.67 g of 2-(3-chloro-2-ethylsulfinylphenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 89).

Workup

  1. additionwas added under ice-
  2. temperaturecooling
  3. extractionextracted with chloroform 2 times
  4. dry with materialThe combined organic layer was dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e8680a5d253e43a9850f68b31c4d843e
Source dataset
uspto-grants-2014_10
Patent number
US08853238B2

Reaction notes

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