Thiosulfate ion → 2-(2-ethylsulfonylphenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine

HRID 923738Notes

Reaction equation

HRID 923738 reaction equation
C(S[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[N:22]([CH3:23])[C:13]2=[N:14][CH:15]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:17]=[C:12]2[N:11]=1)C.Cl[C:25]1C=CC=C(C(OO)=O)[CH:26]=1.[Na].[S:36]([O-:40])([O-])(=[O:38])=S>C(Cl)(Cl)Cl>[CH2:25]([S:36]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[N:22]([CH3:23])[C:13]2=[N:14][CH:15]=[C:16]([C:18]([F:21])([F:19])[F:20])[CH:17]=[C:12]2[N:11]=1)(=[O:40])=[O:38])[CH3:26]

Participants

6

Reactant 4

HCID 1084Thiosulfate ionHCID 70297m-Chloroperbenzoic acidHCID 5360545SodiumHCID 867081912-(2-ethylsulfanylphenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine

Product 1

HCID 867081932-(2-ethylsulfonylphenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a mixture of 2-(2-ethylsulfanylphenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (0.25 g) and chloroform (3 ml), 3-chloroperbenzoic acid (purity: not less than 65%, 0.43 g) was added under ice-cooling, and then heated to room temperature, and stirred for 1 hour. To the reaction mixture, chloroform was added under ice-cooling, and then saturated aqueous sodium, thiosulfate solution was poured, and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium hydrogen carbonate solution, then saturated trine, dried over sodium sulfate, and concentrated under reduced pressure. The obtained crystal was washed with hexane, then methyl-tert-butyl ether to give 0.27 g of 2-(2-ethylsulfonylphenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 6).

Workup

  1. additionwas added under ice-
  2. temperaturecooling
  3. temperaturecooling
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with saturated aqueous sodium hydrogen carbonate solution
  6. dry with materialsaturated trine, dried over sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. washThe obtained crystal was washed with hexane

Sources & evidence

ORD record
ord-7baa4351a19b47b28a643401a0a0ddbb
Source dataset
uspto-grants-2016_03
Patent number
US09278983B2

Reaction notes

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