反应详情

温度

-5 °C

The reaction mixture of 2-(methylthio)-6-(quinolin-4-yloxy)benzo[d]thiazole (460 mg, 1.415 mmol) was dissolved in 8 ml of DCM and cooled to −5° C. A solution was made of 77% MCPBA (333 mg, 1.486 mmol) and 6 ml of DCM. This solution was added to above cooled reaction mixture dropwise over 3-4 minutes. The reaction was stirred at −5° C. for 10 minutes, stirred at RT. for 90 minutes. The reaction followed by LC indicated 95% completed and stalled. A new solution was made of 77% MCPBA (25 mg, 0.1132 mmol) and 1 ml of DCM. This solution was added to above RT. reaction mixture dropwise. The reaction was stirred for 90 minutes more with LC indicating the reaction was complete. The reaction was worked up by adding 80 ml of DCM and 25 ml of a 10% sodium thiosulfate solution and stirred at RT. for 10 minutes. Aqueous layer was extracted and the DCM layer was washed with 25 ml of saturated NaHCO3, 2×25 ml 5% NaHCO3 solution, 1×25 ml water, 1×25 ml saturated NaCl, dried with sodium sulfate. About 1 gram of Silica gel was added and stirred for 10 minutes. The mixture was filtered and concentrated in vacuo to give 2-(methylsulfinyl)-6-(quinolin-4-yloxy)benzo[d]thiazole as solid (357 mg). ES/MS m/z 341.0 (MH+).

1. additionThis solution was added
2. temperatureto above cooled
3. customreaction mixture dropwise over 3-4 minutes
4. stirringstirred at RT
5. waitfor 90 minutes
6. additionThis solution was added to above RT
7. customreaction mixture dropwise
8. stirringThe reaction was stirred for 90 minutes more with LC
9. stirringstirred at RT
10. waitfor 10 minutes
11. extractionAqueous layer was extracted
12. washthe DCM layer was washed with 25 ml of saturated NaHCO3, 2×25 ml 5% NaHCO3 solution, 1×25 ml water, 1×25 ml saturated NaCl
13. dry with materialdried with sodium sulfate
14. additionAbout 1 gram of Silica gel was added
15. stirringstirred for 10 minutes
16. filtrationThe mixture was filtered
17. concentrationconcentrated in vacuo