反应详情

3,4-diethoxythiobenzamide (30.0 g, 133 mmol) was suspended in ethanol (300 ml), and 1,3-dichloroacetone (12.8 ml, 135 mmol) was added, followed by heating under reflux for 4 hours. After cooling to room temperature, the solvent was distilled off under reduced pressure, and the residue was subjected to extraction with ethyl acetate. The organic layer was washed with a saturated aqueous sodium hydrogencarbonate solution, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/3). The solvent was distilled off under reduced pressure, and the residue was recrystallized from an ethyl acetate/n-hexane mixed solvent, to thereby obtain 26.9 g (yield: 68%) of 4-chloromethyl-2-(3,4-diethoxyphenyl)thiazole as yellow prisms.

1. temperatureby heating
2. temperatureunder reflux for 4 hours
3. distillationthe solvent was distilled off under reduced pressure
4. extractionthe residue was subjected to extraction with ethyl acetate
5. washThe organic layer was washed with a saturated aqueous sodium hydrogencarbonate solution
6. dry with materialdried over anhydrous sodium sulfate
7. distillationThe solvent was distilled off under reduced pressure
8. customthe residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/3)
9. distillationThe solvent was distilled off under reduced pressure
10. customthe residue was recrystallized from an ethyl acetate/n-hexane mixed solvent