反应详情

1-Amino-3-methylthiobenzene (1.27 ml, 10 mmol) was dissolved in tetrahydrofuran (10 ml), and then triethylamine (1.46 ml, 10.5 mmol) and phenyl chloroformate (1.32 ml, 10.5 mmol) were added dropwise in that order at room temperature under a nitrogen atmosphere and the mixture was stirred overnight. The reaction solution was distributed between ethyl acetate and water, and the organic layer was washed with saturated saline and dried over anhydrous sodium sulfate. After distilling off the solvent and drying under reduced pressure, the residue was dissolved in dichloromethane (50 ml), and 3-chloroperbenzoic acid (4.93 g, 20 mmol) was gradually added while cooling in an ice water bath. An aqueous saturated solution of sodium thiosulfate was added to the reaction solution, and then the insoluble portion was filtered off, and extraction with ethyl acetate was followed by washing with an aqueous saturated solution of sodium carbonate and drying over anhydrous sodium sulfate. The solvent was distilled off, and the residue was purified by silica gel column chromatography (ethyl acetate-hexane=1:1) to obtain the title compound (2.545 g, 8.74 mmol, 87.4%) as white crystals.

1. washthe organic layer was washed with saturated saline
2. dry with materialdried over anhydrous sodium sulfate
3. distillationAfter distilling off the solvent
4. customdrying under reduced pressure
5. dissolutionthe residue was dissolved in dichloromethane (50 ml)
6. temperaturewhile cooling in an ice water bath
7. filtrationthe insoluble portion was filtered off
8. extractionextraction with ethyl acetate
9. washby washing with an aqueous saturated solution of sodium carbonate
10. dry with materialdrying over anhydrous sodium sulfate
11. distillationThe solvent was distilled off
12. customthe residue was purified by silica gel column chromatography (ethyl acetate-hexane=1:1)