反应详情

温度

0 °C

A mixture of 0.5 g (1.85 mmol) of (E)-2-methyl-N-phenyl-3-(phenylthio)-2-propenamide, 0.4 ml of thionyl chloride, 5 mg of DMF, and 10 ml of toluene was refluxed for 1 hour and then concentrated. The residue was dissolved in 5 ml of DMF and cooled to 0° C. To a solution of 277 mg (2.23 mmol) of 2-methylthiophenol in 5 ml of DMF was added 90 mg of sodium hydride (60% in oil) under ice cooling and stirred for 5 minutes. The solution was added portionwise to the above-described DMF solution of the residue under ice cooling and stirred at room temperature for 1 hour. The reaction mixture was poured into water and extracted with tert-butyl methyl ether (three times). The combined organic layer was washed sequentially with water and a saturated NaCl solution, dried over anhydrous MgSO4, and concentrated. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=20/1) to obtain 573 mg of 2-methylphenyl 2-methyl-N-phenyl-3-(phenylthio)-2-propenimidothioate (hereinafter referred to as the present compound 21).

1. temperaturewas refluxed for 1 hour
2. concentrationconcentrated
3. dissolutionThe residue was dissolved in 5 ml of DMF
4. stirringstirred at room temperature for 1 hour
5. extractionextracted with tert-butyl methyl ether (three times)
6. washThe combined organic layer was washed sequentially with water
7. dry with materiala saturated NaCl solution, dried over anhydrous MgSO4
8. concentrationconcentrated
9. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=20/1)