Sodium Thiosulfate → HCID 178477633, compound

HRID 533650Notes

Reaction equation

HRID 533650 reaction equation
C(S[C:4]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[CH:6][C:5]=1[C:14]1[NH:26][C:17]2=[N:18][CH:19]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:21]=[C:16]2[N:15]=1)C.Cl[C:28]1C=CC=C(C(OO)=O)[CH:29]=1.C(=O)([O-])O.[Na+].[S:43]([O-:47])([O-])(=[O:45])=S.[Na+].[Na+]>C(Cl)(Cl)Cl>[CH2:28]([S:43]([C:4]1[CH:9]=[C:8]([C:10]([F:11])([F:12])[F:13])[CH:7]=[CH:6][C:5]=1[C:14]1[NH:26][C:17]2=[N:18][CH:19]=[C:20]([C:22]([F:25])([F:23])[F:24])[CH:21]=[C:16]2[N:15]=1)(=[O:47])=[O:45])[CH3:29]

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 178477282HCID 178477282, compound

Product 1

HCID 178477633HCID 178477633, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a mixture of 2-(2-ethylsulfanyl-4-trifluoromethyl-phenyl)-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (12 g) and chloroform (111 mL), 69-75% of 3-chloroperbenzoic acid (8.0 g) was added under ice-cooling. The mixture was heated to room temperature, and stirred for 0.5 hours. Into the mixture, saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium thiosulfate solution were poured, and extracted with chloroform. The combined organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 9.1 g of 2-(2-ethylsulfonyl-4-trifluoromethyl-phenyl)-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (hereinafter, Present Compound 345).

Workup

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

Sources & evidence

ORD record
ord-a506eda1227e429db0b9ba5016b686fc
Source dataset
uspto-grants-2014_10
Patent number
US08853238B2

Reaction notes

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