Potassium Persulfate → 4-(3-METHYLPHENYL)-5-(2-METHYL-4-PYRIDYL)-2-(4-METHYLSULFINYLPHENYL)-1,3-THIAZOLE

HRID 1727362Notes

Reaction equation

HRID 1727362 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][CH3:27])=[CH:22][CH:21]=3)[S:11][C:12]=2[C:13]2[CH:18]=[CH:17][N:16]=[C:15]([CH3:19])[CH:14]=2)[CH:5]=[CH:6][CH:7]=1.S(OOS([O-])(=O)=O)([O-])(=O)=[O:29].[K+].[K+].C(=O)([O-])O.[Na+]>C(O)(=O)C.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]([CH3:27])=[O:29])=[CH:22][CH:21]=3)[S:11][C:12]=2[C:13]2[CH:18]=[CH:17][N:16]=[C:15]([CH3:19])[CH:14]=2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 24412Potassium PersulfateHCID 516892Sodium BicarbonateHCID 101348914-(3-METHYLPHENYL)-5-(2-METHYL-4-PYRIDYL)-2-[4-(METHYLTHIO)PHENYL]-1,3-THIAZOLE

Product 1

HCID 102229114-(3-METHYLPHENYL)-5-(2-METHYL-4-PYRIDYL)-2-(4-METHYLSULFINYLPHENYL)-1,3-THIAZOLEYield 26.5%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To a solution of 4-(3-methylphenyl)-5-(2-methyl-4-pyridyl)-2-[4-(methylthio)phenyl]-1,3-thiazole (0.55 g, 1.4 mmol) in acetic acid (15 mL) was added a solution of potassium persulfate (0.43 g, 1.6 mmol) in water (8 mL), and the mixture was stirred for 14 hours at room temperature. An aqueous sodium hydrogen carbonate solution was poured into the reaction mixture, and extracted with ethyl acetate. The extracts were washed with water, dried, then, the solvent was distilled off. The residue was purified by column chromatography (filler: Chromatorex NH DM1020 (trade name, manufactured by Fuji Silysia Chemical Ltd.), hexane-ethyl acetate=1:4), and recrystallized from ethyl acetate-hexane to obtain a title compound (0.15 g, yield 26%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extracts were washed with water
  3. customdried
  4. distillationthe solvent was distilled off
  5. customThe residue was purified by column chromatography (filler: Chromatorex NH DM1020 (trade name, manufactured by Fuji Silysia Chemical Ltd.), hexane-ethyl acetate=1:4)
  6. customrecrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-d842e8909a8641f28a3b4a40a337a983
Source dataset
uspto-grants-2009_02
Patent number
US07495018B2

Reaction notes

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