Acetic Acid → HCID 86708200, compound

HRID 533604Notes

Reaction equation

HRID 533604 reaction equation
[CH3:1][N:2]1[C:6]2=[N:7][CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=[C:5]2[N:4]=[C:3]1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[S:21][C:22]([F:25])([F:24])[F:23].C(O)(=[O:28])C.OO.[OH2:32]>>[CH3:1][N:2]1[C:6]2=[N:7][CH:8]=[C:9]([C:11]([F:13])([F:14])[F:12])[CH:10]=[C:5]2[N:4]=[C:3]1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[S:21]([C:22]([F:25])([F:23])[F:24])(=[O:28])=[O:32]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 784Hydrogen PeroxideHCID 962WaterHCID 86708199HCID 86708199, compound

Product 1

HCID 86708200HCID 86708200, compound

Conditions

Temperature
80 °C

Procedure

A mixture of 3-methyl-6-trifluoromethyl-2-(2-trifluoromethylsulfanylphenyl)-3H-imidazo[4,5-b]pyridine (0.25 g) and acetic acid (7 ml) was heated to 80° C., and 30% of an aqueous solution of hydrogen peroxide (3 ml) was added dropwise thereto. The mixture was heated to 100° C., and then stirred with heating for 5 hours. Into the reaction mixture cooled to room temperature, water was poured, and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 76 mg of 3-methyl-6-trifluoromethyl-2-(2-trifluoromethylsulfonylphenyl)-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 20).

Workup

  1. temperatureThe mixture was heated to 100° C.
  2. temperaturewith heating for 5 hours
  3. temperatureInto the reaction mixture cooled to room temperature
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-aca3960610854dc9bc2a5937a368fb50
Source dataset
uspto-grants-2014_10
Patent number
US08853238B2

Reaction notes

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