Aspirin → 4-Isothiocyanatophenyl 2-acetoxybenzoate

Temperature

0 °C

To the solution of 1 (aspirin, 1200 mg, 6.67 mmol) in 60 mL of dimethylformamide, hydroxybenzotriazole (992 mg, 7.34 mmol) and DCC (1520 mg, 7.34 mmol) were added with stirring at 0° C. for 1 h. To the reaction mixture 4-hydroxyphenylisothiocyanate (2; 1109 mg, 7.34 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 and the precipitate was removed. The solvent was evaporated and the crude product was loaded on a silica gel open column and eluted with chloroform/n-hexane 6:4, from which 4-isothiocyanatophenyl 2-acetoxybenzoate (3) was obtained (150 mg, 7% 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. customthe precipitate was removed
7. customThe solvent was evaporated
8. washeluted with chloroform/n-hexane 6:4, from which 4-isothiocyanatophenyl 2-acetoxybenzoate (3)
9. customwas obtained (150 mg, 7% yield)

ORD record

ord-7f65cfde5e3e4cd1be0d862d3f8b9bd1

Source dataset

uspto-grants-2013_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08541398B2