反应详情

温度

0 °C

To the solution of 1 (naproxen, 595 mg, 2.58 mmol) in 20 mL of dimethylformamide, hydroxybenzotriazole (388 mg, 2.87 mmol) and DCC (593 mg, 2.87 mmol) were added with stirring at 0° C. for 1 h. To the reaction mixture 5-p-hydroxyphenyl-1,2-dithiole-3-thione (2; 650 mg, 2.87 mmol) was added and stirred for 1 h at 0° C. and 2 h at room temperature. After filtration, the filtrate was evaporated under reduced pressure to remove the solvent. The oily residue thus obtained was dissolved in ethyl acetate; the organic layer was washed with brine, with NaHCO3 5%, with citric acid 10% and than dried on anhydrous MgSO4, filtered and the solvent evaporated. The crude product was loaded on a silica gel open column and eluted with dichloromethane, from which 4-(5-thioxo-5H-1,2-dithiol-3-yl)phenyl 2-(2-methoxynaphthalen-6-yl)propanoate (3) was obtained (406 mg, 36% yield).

1. stirringstirred for 1 h at 0° C. and 2 h at room temperature
2. filtrationAfter filtration
3. customthe filtrate was evaporated under reduced pressure
4. customto remove the solvent
5. customThe oily residue thus obtained
6. washthe organic layer was washed with brine, with NaHCO3 5%, with citric acid 10%
7. dry with materialthan dried on anhydrous MgSO4
8. filtrationfiltered
9. customthe solvent evaporated
10. washeluted with dichloromethane, from which 4-(5-thioxo-5H-1,2-dithiol-3-yl)phenyl 2-(2-methoxynaphthalen-6-yl)propanoate (3)
11. customwas obtained (406 mg, 36% yield)