Thiophenol → 4-(3-Methylphenyl)-2-(4-methylsulfonylphenyl)-5-(2-phenylthio-4-pyridyl)-1,3-thiazole

HRID 2212356Notes

Reaction equation

HRID 2212356 reaction equation
F[C:2]1[CH:7]=[C:6]([C:8]2[S:12][C:11]([C:13]3[CH:18]=[CH:17][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:15][CH:14]=3)=[N:10][C:9]=2[C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([CH3:29])[CH:24]=2)[CH:5]=[CH:4][N:3]=1.[C:30]1([SH:36])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C(=O)([O-])O.[Na+]>>[CH3:29][C:25]1[CH:24]=[C:23]([C:9]2[N:10]=[C:11]([C:13]3[CH:18]=[CH:17][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:15][CH:14]=3)[S:12][C:8]=2[C:6]2[CH:5]=[CH:4][N:3]=[C:2]([S:36][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH:7]=2)[CH:28]=[CH:27][CH:26]=1

Participants

4

Reactant 3

HCID 7969ThiophenolHCID 516892Sodium BicarbonateHCID 102739295-(2-Fluoro-4-pyridyl)-4-(3-methylphenyl)-2-(4-methylsulfonylphenyl)-1,3-thiazole

Product 1

HCID 219642574-(3-Methylphenyl)-2-(4-methylsulfonylphenyl)-5-(2-phenylthio-4-pyridyl)-1,3-thiazoleYield 70.3%

Conditions

Temperature
150 °C

Procedure

A mixture of 5-(2-fluoro-4-pyridyl)-4-(3-methylphenyl)-2-(4-methylsulfonylphenyl)-1,3-thiazole (0.40 g, 0.94 mmol) and thiophenol (1.0 mL, 9.7 mmol) was stirred at 150° C. for 10 hours. After the reaction mixture was cooled to room temperature, a saturated aqueous solution of sodium hydrogencarbonate was added, the resulting mixture was extracted with ethyl acetate and washed with water. This extract was dried and concentrated. The residue was purified by silica gel column chromatography (hexane:ethyl acetate, 1:1) and recrystallized from ethanol to obtain 0.34 g (yield 70%) of the title compound.

Workup

  1. temperatureAfter the reaction mixture was cooled to room temperature
  2. extractionthe resulting mixture was extracted with ethyl acetate
  3. washwashed with water
  4. customThis extract was dried
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate, 1:1)
  7. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-c3270669efed4077802e8ea968d95b16
Source dataset
uspto-grants-2006_09
Patent number
US07101899B1

Reaction notes

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