반응 #46913

반응 방정식

4-hydroxyphenylisothiocyanate

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

naproxene

hydroxybenzotriazole

DCC

→

4-(isothiocyano)-phenyl 2-(2-methoxynaphthalen-6-yl)propanoate

수율 21.0%

용매

ethyl acetate

dimethylformamide

반응 조건

후처리

1. 1
   workup.STIRRINGstirred for 1 h at 0° C. and 2 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
   기타the precipitate was removed
7. 7
   기타The solvent was evaporated
8. 8
   세척eluted with dichloromethane, from which 4-(isothiocyano)-phenyl 2-(2-methoxynaphthalen-6-yl)propanoate (3)
9. 9
   기타was obtained (230 mg, 21% yield)

실험 절차

To the solution of 1 (naproxene, 691 mg, 3 mmol) in 20 mL of dimethylformamide, hydroxybenzotriazole (446 mg, 3.3 mmol) and DCC (619 mg, 3.3 mmol) were added with stirring at 0° C. for 1 h. To the reaction mixture 4-hydroxyphenylisothiocyanate (2; 500 mg, 3.3 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 dichloromethane, from which 4-(isothiocyano)-phenyl 2-(2-methoxynaphthalen-6-yl)propanoate (3) was obtained (230 mg, 21% yield).

출처