Acetic Acid → HCID 86708215, compound

HRID 533624Notes

Reaction equation

HRID 533624 reaction equation
[Cl:1][C:2]1[C:3]([S:22]([CH2:24][CH3:25])=[O:23])=[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.C(O)(=[O:28])C.OO>O>[Cl:1][C:2]1[C:3]([S:22]([CH2:24][CH3:25])(=[O:28])=[O:23])=[C:4]([C:8]2[N:20]([CH3:21])[C:11]3=[N:12][CH:13]=[C:14]([C:16]([F:19])([F:17])[F:18])[CH:15]=[C:10]3[N:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 784Hydrogen PeroxideHCID 86708213HCID 86708213, compound

Product 1

HCID 86708215HCID 86708215, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2-(3-chloro-2-ethylsulfinylphenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (0.48 g) and acetic acid (12 ml) was stirred with heating at 80° C., and then 30% of an aqueous solution of hydrogen peroxide (6 ml) was added dropwise. The mixture was heated to 100° C., and stirred with heating for 3 hours. Into the reaction mixture cooled to room temperature, water was poured, and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium hydrogen carbonate solution, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 0.21 g of 2-(3-chloro-2-ethylsulfonylphenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 90).

Workup

  1. temperatureThe mixture was heated to 100° C.
  2. stirringstirred
  3. temperaturewith heating for 3 hours
  4. temperatureInto the reaction mixture cooled to room temperature
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with saturated aqueous sodium hydrogen carbonate solution
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-72e558c30128430292acf79323b40456
Source dataset
uspto-grants-2014_10
Patent number
US08853238B2

Reaction notes

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