반응 #2267058

반응 방정식

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

용매

ethyl acetate

반응 조건

후처리

1. 1
   온도The mixture was heated
2. 2
   온도to reflux
3. 3
   온도at reflux over night
4. 4
   온도As the mixture warmed the cream suspension
5. 5
   workup.DISSOLUTIONgradually dissolved
6. 6
   온도Just before refluxing
7. 7
   기타formed
8. 8
   여과filtered
9. 9
   세척the residue was washed well with ethanol
10. 10
    농축The resulting filtrate was concentrated to dryness
11. 11
    기타to give an off-white solid
12. 12
    세척washed with 1) water (800 mL) and 2) brine (1 L)
13. 13
    건조The filtrate was dried (MgSO4)
14. 14
    농축concentrated to dryness
15. 15
    기타An off-white solid was obtained
16. 16
    기타that was recrystallised
17. 17
    세척The filtered material was washed well with acetonitrile
18. 18
    기타dried (Vac/40° C.)

실험 절차

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%.

출처