反応 #62701

反応方程式

2-(2-pinanylthio)-5-mercapto-1,3,4-thiadiazole

1,2-epoxyhexadecane

2,5-Dimercapto-1,3,4-thiadiazole

alphapinene

→

2-(2-Pinanylthio)-5-(2-hydroxyhexadecylthio)-1,3,4-thiadiazole

溶媒

isopropanol

反応条件

後処理

1. 1
   その他(exothermic reaction)
2. 2
   温度The reaction was maintained at 135° C. for one hour
3. 3
   その他was stripped under vacuum at 135° C.
4. 4
   その他to remove any unreacted pinene
5. 5
   ろ過filtered hot
6. 6
   workup.ADDITIONMethanol (200 ml), hexane (150 ml) and water (15 ml) were charged
7. 7
   その他The hexane layer was removed
8. 8
   その他The methanol layer was stripped of methanol by rotary evaporation
9. 9
   workup.ADDITIONthe intermediate product residue was mixed with toluene (200 ml)
10. 10
    抽出extracted with 1M sodium bicarbonate solution (50 ml)
11. 11
    乾燥The toluene layer was dried over magnesium sulfate
12. 12
    その他the solvent removed by rotary evaporation
13. 13
    その他the reaction
14. 14
    温度to reflux
15. 15
    その他The solvent was then stripped by rotary evaporation
16. 16
    その他to afford the product

実験手順

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.

出典