تفاعل #2267058

معادلة التفاعل

Sodium hydroxide

2-methylpentyl methanesulphonate

ethanol

2-mercapto-1,3,4-thiadiazole-5-amine

→

required product

2-(2-Methylpentylthio)-1,3,4-thiadiazole-5-amine

المذيبات

ethyl acetate

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe mixture was heated
2. 2
   درجة الحرارةto reflux
3. 3
   درجة الحرارةat reflux over night
4. 4
   درجة الحرارةAs the mixture warmed the cream suspension
5. 5
   workup.DISSOLUTIONgradually dissolved
6. 6
   درجة الحرارةJust before refluxing
7. 7
   أخرىformed
8. 8
   ترشيحfiltered
9. 9
   غسيلthe residue was washed well with ethanol
10. 10
    تركيزThe resulting filtrate was concentrated to dryness
11. 11
    أخرىto give an off-white solid
12. 12
    غسيلwashed with 1) water (800 mL) and 2) brine (1 L)
13. 13
    تجفيفThe filtrate was dried (MgSO4)
14. 14
    تركيزconcentrated to dryness
15. 15
    أخرىAn off-white solid was obtained
16. 16
    أخرىthat was recrystallised
17. 17
    غسيلThe filtered material was washed well with acetonitrile
18. 18
    أخرىdried (Vac/40° C.)

الإجراء التجريبي

A three-necked 3-L round bottom flask was charged with 2-methylpentyl methanesulphonate (90 g, 0.5 mol), ethanol (1.5 L) and 2-mercapto-1,3,4-thiadiazole-5-amine (66.5 g, 0.5 mol). Sodium hydroxide (20 g, 0.5 mol) was added to the stirred suspension. The mixture was heated to reflux and held at reflux over night. As the mixture warmed the cream suspension gradually dissolved. Just before refluxing began a cloudy precipitate formed. The reaction mixture was cooled to room temperature, filtered, and the residue was washed well with ethanol. The resulting filtrate was concentrated to dryness to give an off-white solid that was dissolved in ethyl acetate (1.2 L) and washed with 1) water (800 mL) and 2) brine (1 L). The filtrate was dried (MgSO4) and concentrated to dryness. An off-white solid was obtained that was recrystallised from boiling acetonitrile (150 mL). The filtered material was washed well with acetonitrile and dried (Vac/40° C.). The required product was obtained as a white solid wt 83 g; 76.5%.

المصدر