تفاعل #62701

معادلة التفاعل

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

المذيبات

isopropanol

ظروف التفاعل

المعالجة

1. 1
   أخرى(exothermic reaction)
2. 2
   درجة الحرارةThe reaction was maintained at 135° C. for one hour
3. 3
   أخرىwas stripped under vacuum at 135° C.
4. 4
   أخرىto remove any unreacted pinene
5. 5
   ترشيحfiltered hot
6. 6
   workup.ADDITIONMethanol (200 ml), hexane (150 ml) and water (15 ml) were charged
7. 7
   أخرىThe hexane layer was removed
8. 8
   أخرىThe methanol layer was stripped of methanol by rotary evaporation
9. 9
   workup.ADDITIONthe intermediate product residue was mixed with toluene (200 ml)
10. 10
    استخلاصextracted with 1M sodium bicarbonate solution (50 ml)
11. 11
    تجفيفThe toluene layer was dried over magnesium sulfate
12. 12
    أخرىthe solvent removed by rotary evaporation
13. 13
    أخرىthe reaction
14. 14
    درجة الحرارةto reflux
15. 15
    أخرىThe solvent was then stripped by rotary evaporation
16. 16
    أخرىto afford the product

الإجراء التجريبي

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.

المصدر