反应详情

温度

40 °C

To a 0° C. solution of 2-methyl-5-phenylnicotinic acid (100 mg, 0.40 mmol) in CH2Cl2 (4 mL) was added oxalyl chloride (344 μL, 4.0 mmol). The mixture was stirred at 40° C. After 3 hours, the mixture was concentrated to dryness, dissolved in benzene (2×5 mL) and concentrated again. After dissolving the crude residue in CH2Cl2 (2 mL) at 0° C., pyridine (1 mL, 0.92 M in CH2Cl2), 4-dimethylaminopyridine (10 mg, 0.08 mmol) and 4-methylthiophenol (60 mg, 0.48 mmol) were added. The mixture was then allowed to warm to room temperature. After stirring for 2 hours, the mixture was diluted with EtOAc, washed with 1N HCl, brine, dried over sodium sulfate, filtered, and concentrated. The crude residue was purified by flash chromatography (100-80% hexanes/EtOAc gradient) to afford the title compound. LRMS (APCI) calculated for C20H18NOS [M+H]+, 320.1; found 320.1

1. concentrationthe mixture was concentrated to dryness
2. dissolutiondissolved in benzene (2×5 mL)
3. concentrationconcentrated again
4. dissolutionAfter dissolving the crude residue in CH2Cl2 (2 mL) at 0° C.
5. temperatureto warm to room temperature
6. stirringAfter stirring for 2 hours
7. washwashed with 1N HCl, brine
8. dry with materialdried over sodium sulfate
9. filtrationfiltered
10. concentrationconcentrated
11. customThe crude residue was purified by flash chromatography (100-80% hexanes/EtOAc gradient)