Aspirin → 4-(3-Thioxo-3H-1,2-dithiol-5-yl)phenyl 2-acetoxybenzoate

Temperature

0 °C

To the solution of 1 (acetylsalicylic acid, 416 mg, 2.31 mmol) in 40 mL of dimethylformamide, hydroxybenzotriazole (343 mg, 2.54 mmol) and DCC (523 mg, 2.54 mmol) were added with stirring at 0° C. for 1 h. To the reaction mixture 5-p-hydroxyphenyl-1,2-dithiole-3-thione (2; 574 mg, 2.54 mmol) was added and stirred for 1 h at 0° C. and 3 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, dried on anhydrous MgSO4, filtered and the solvent evaporated. The crude product was loaded on a silica gel open column and eluted with ethyl ether/petroleum ether (1/1), from which 4-(5-thioxo-5H-1,2-dithiol-3-yl)phenyl 2-acetoxybenzoate (3) was obtained (354 mg, 40% yield).

1. stirringstirred for 1 h at 0° C. and 3 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
7. dry with materialdried on anhydrous MgSO4
8. filtrationfiltered
9. customthe solvent evaporated
10. washeluted with ethyl ether/petroleum ether (1/1), from which 4-(5-thioxo-5H-1,2-dithiol-3-yl)phenyl 2-acetoxybenzoate (3)
11. customwas obtained (354 mg, 40% yield)

ORD record

ord-0784ea4004a047fb97965e31f554cde6

Source dataset

uspto-grants-2010_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07741359B2