反应详情

Rhodanine (0.052 g, 0.388 mmol, 1.0 eq.) was dissolved in EtOH (2 ml) and 2 M NaOH (0.275 ml, 0.550 mmol, 1.42 eq.) with vigorous stirring. Once the Rhodanine was completely dissolved, 6-Chloroacetyl-1,4-benzodioxane (0.080 g, 0.380 mmol, 0.98 eq.) was added with constant stirring. (It should be noted that α-chloro ketones were used when the corresponding α-bromo ketones were not available.) The reaction was mixed overnight at 40° C. After 18 hrs the reaction was removed from the heat and left stirring at room temp for 48 hrs. The resulting reaction mixture was then diluted with water (5 ml) and extracted with dichloromethane (3×5 ml). The organic layer was dried over Na2SO4 and then evaporated to yield an oil. The oil was purified by chromatotron using a 50/50 mixture of ethyl acetate in hexanes as the mobile phase. The purified product, Compound 34, was then recrystallized in hexanes to complete its purification (20 mg, 0.0646 mmol, 17%). The product was characterized by 1H-NMR: (CDCl3) 7.55 (q, 2H), 6.93 (d, 1H), 4.93 (s, 2H), 4.31 (m, 4H), 4.02 (s, 2H) ppm. In addition LCMS [ES+] analysis yielded a single peak, 310 [M]+ m/e.

1. addition) The reaction was mixed overnight at 40° C
2. customAfter 18 hrs the reaction was removed from the
3. temperatureheat
4. waitleft
5. customThe resulting reaction mixture
6. extractionextracted with dichloromethane (3×5 ml)
7. dry with materialThe organic layer was dried over Na2SO4
8. customevaporated
9. customto yield an oil
10. customThe oil was purified by chromatotron
11. additiona 50/50 mixture of ethyl acetate in hexanes as the mobile phase
12. customThe purified product, Compound 34, was then recrystallized in hexanes
13. customits purification (20 mg, 0.0646 mmol, 17%)
14. additionIn addition LCMS [ES+] analysis
15. customyielded a single peak, 310 [M]+ m/e