反应详情

A suspension of 2H-1,2-benzothiazin-4(3H)-one 1,1-dioxide ethylene ketal (0.48 g, 2 mmol) and 60% sodium hydride (0.08 g, 2 mmol.) in 1,2-dimethoxyethane (20 mL) was heated for one hour under refluxing. The resulting reaction liquid was further heated for 16 hours under refluxing, after addition of 1-chloro-3-morpholino-2-propanol (0.36 g, 2 mmol.). The reaction liquid was placed under reduced pressure to distill the solvent off. The residue was treated with 1N hydrochloric acid and ethyl acetate, and the aqueous layer was taken out. The aquous solution was made basic by addition of potassium carbonate, and the precipitated oil was extracted with ethyl acetate. The extract solution was washed with an aqueous saturated sodium chloride solution, and dried over anhydrous sodium sulfate. The dried solution was placed under reduced pressure to distill the solvent off. The resulting residue was treated by silica gel column chromatography (ethyl acetate/methanol=10/1) to give the desired compound (0.54 g, yield 70%) as a colorless oil.

1. temperaturewas heated for one hour
2. temperatureunder refluxing
3. customThe resulting reaction liquid
4. temperaturewas further heated for 16 hours
5. temperatureunder refluxing
6. customThe reaction liquid
7. distillationto distill the solvent off
8. additionThe residue was treated with 1N hydrochloric acid and ethyl acetate
9. additionThe aquous solution was made basic by addition of potassium carbonate
10. extractionthe precipitated oil was extracted with ethyl acetate
11. washThe extract solution was washed with an aqueous saturated sodium chloride solution
12. dry with materialdried over anhydrous sodium sulfate
13. distillationto distill the solvent off
14. additionThe resulting residue was treated by silica gel column chromatography (ethyl acetate/methanol=10/1)