反应详情

温度

120 °C

2,5-Dimercapto-1,3,4-thiadiazole (161.3 g, 1.08 mol) and alphapinene (161.3 g, 1.18 mol) were charged to a reaction vessel and cautiously heated to 120° C. (exothermic reaction). The reaction was maintained at 135° C. for one hour. The intermediate product was stripped under vacuum at 135° C. to remove any unreacted pinene and filtered hot. Methanol (200 ml), hexane (150 ml) and water (15 ml) were charged. The hexane layer was removed and discharded. The methanol layer was stripped of methanol by rotary evaporation and the intermediate product residue was mixed with toluene (200 ml) and then extracted with 1M sodium bicarbonate solution (50 ml). The toluene layer was dried over magnesium sulfate and the solvent removed by rotary evaporation. The yield was 134.1 g (0.468 mol) of the purified intermediate, 2-(2-pinanylthio)-5-mercapto-1,3,4-thiadiazole. This product was reacted with 1,2-epoxyhexadecane (112.3 g, 0.468 mol) by charging both reagents and isopropanol (100 ml) and bringing the reaction to reflux. The solvent was then stripped by rotary evaporation to afford the product.

1. custom(exothermic reaction)
2. temperatureThe reaction was maintained at 135° C. for one hour
3. customwas stripped under vacuum at 135° C.
4. customto remove any unreacted pinene
5. filtrationfiltered hot
6. additionMethanol (200 ml), hexane (150 ml) and water (15 ml) were charged
7. customThe hexane layer was removed
8. customThe methanol layer was stripped of methanol by rotary evaporation
9. additionthe intermediate product residue was mixed with toluene (200 ml)
10. extractionextracted with 1M sodium bicarbonate solution (50 ml)
11. dry with materialThe toluene layer was dried over magnesium sulfate
12. customthe solvent removed by rotary evaporation
13. customthe reaction
14. temperatureto reflux
15. customThe solvent was then stripped by rotary evaporation
16. customto afford the product