Ammonium Persulfate → (4-{2-[4-(Methanesulfonyl)phenyl]-4-(3-methylphenyl)-1,3-thiazol-5-yl}pyridin-2-yl)methanol

HRID 1727367Notes

Reaction equation

HRID 1727367 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:8]2[N:9]=[C:10]([C:20]3[CH:25]=[CH:24][C:23]([S:26]([CH3:29])(=[O:28])=[O:27])=[CH:22][CH:21]=3)[S:11][C:12]=2[C:13]2[CH:18]=[CH:17][N+:16]([O-])=[CH:15][CH:14]=2)[CH:5]=[CH:6][CH:7]=1.F[B-](F)(F)F.[CH3:35][O+:36](C)C.S(OOS([O-])(=O)=O)([O-])(=O)=O.[NH4+].[NH4+]>C(Cl)Cl.O>[CH3:1][C:2]1[CH:3]=[C:4]([C:8]2[N:9]=[C:10]([C:20]3[CH:25]=[CH:24][C:23]([S:26]([CH3:29])(=[O:28])=[O:27])=[CH:22][CH:21]=3)[S:11][C:12]=2[C:13]2[CH:18]=[CH:17][N:16]=[C:15]([CH2:35][OH:36])[CH:14]=2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 62648Ammonium Persulfate2×HCID 2735153Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1)HCID 573772244-{2-[4-(Methanesulfonyl)phenyl]-4-(3-methylphenyl)-1,3-thiazol-5-yl}-1-oxo-1lambda~5~-pyridine

Product 1

HCID 53426476(4-{2-[4-(Methanesulfonyl)phenyl]-4-(3-methylphenyl)-1,3-thiazol-5-yl}pyridin-2-yl)methanolYield 61%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-[4-(3-methylphenyl)-2-(4-methylsulfonylphenyl)-1,3-thiazol-5-yl]pyridine N-oxide (0.43 g, 1.0 mmol) in methylene chloride (10 mL) was added trimethyloxonium tetrafluoroborate (0.17 g, 1.2 mmol), and the mixture was stirred for 2 hours. The reaction mixture was concentrated under reduced pressure, and methanol (15 mL) was added to the residue. To the mixture was added a solution of ammonium persulfate (0.05 g, 0.22 mmol) in water (1 mL) under reflux, and the mixture was heated to reflux for 30 minutes. A solution of ammonium persulfate (0.03 g, 0.11 mmol) in water. (1 mL) was added to the reaction mixture, and the mixture was further heated to reflux for 13 hours. The reaction mixture was cooled to room temperature, then, concentrated under reduced pressure. To the residue was added an aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The extracts were washed with brine, dried over magnesium sulfate, and filtrated and concentrated under reduced pressure. The residued was purified by column chromatography (filler: Chromatorex NH DM1020 (trade name, manufactured by Fuji Silysia Chemical Ltd.), ethyl acetate) to obtain a title compound (0.26 g, yield 61%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, and methanol (15 mL)
  2. additionwas added to the residue
  3. temperatureunder reflux
  4. temperaturethe mixture was heated
  5. temperatureto reflux for 30 minutes
  6. addition(1 mL) was added to the reaction mixture
  7. temperaturethe mixture was further heated
  8. temperatureto reflux for 13 hours
  9. concentrationconcentrated under reduced pressure
  10. additionTo the residue was added an aqueous sodium hydrogen carbonate solution
  11. extractionextracted with ethyl acetate
  12. washThe extracts were washed with brine
  13. dry with materialdried over magnesium sulfate
  14. filtrationfiltrated
  15. concentrationconcentrated under reduced pressure
  16. customThe residued was purified by column chromatography (filler: Chromatorex NH DM1020 (trade name, manufactured by Fuji Silysia Chemical Ltd.), ethyl acetate)

Sources & evidence

ORD record
ord-ff4c5080db18492a97f2252ec34e2b16
Source dataset
uspto-grants-2009_02
Patent number
US07495018B2

Reaction notes

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