반응 #46906

반응 방정식

5-p-hydroxyphenyl-1,2-dithiole-3-thione

acetylsalicylic acid

hydroxybenzotriazole

DCC

→

4-(5-thioxo-5H-1,2-dithiol-3-yl)phenyl 2-acetoxybenzoate

수율 40.0%

용매

ethyl acetate

dimethylformamide

반응 조건

후처리

1. 1
   workup.STIRRINGstirred for 1 h at 0° C. and 3 h at room temperature
2. 2
   여과After filtration
3. 3
   기타the filtrate was evaporated under reduced pressure
4. 4
   기타to remove the solvent
5. 5
   기타The oily residue thus obtained
6. 6
   세척the organic layer was washed with brine
7. 7
   건조dried on anhydrous MgSO4
8. 8
   여과filtered
9. 9
   기타the solvent evaporated
10. 10
    세척eluted with ethyl ether/petroleum ether (1/1), from which 4-(5-thioxo-5H-1,2-dithiol-3-yl)phenyl 2-acetoxybenzoate (3)
11. 11
    기타was obtained (354 mg, 40% yield)

실험 절차

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).

출처