反応 #2267058

反応方程式

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

溶媒

ethyl acetate

反応条件

後処理

1. 1
   温度The mixture was heated
2. 2
   温度to reflux
3. 3
   温度at reflux over night
4. 4
   温度As the mixture warmed the cream suspension
5. 5
   workup.DISSOLUTIONgradually dissolved
6. 6
   温度Just before refluxing
7. 7
   その他formed
8. 8
   ろ過filtered
9. 9
   洗浄the residue was washed well with ethanol
10. 10
    濃縮The resulting filtrate was concentrated to dryness
11. 11
    その他to give an off-white solid
12. 12
    洗浄washed with 1) water (800 mL) and 2) brine (1 L)
13. 13
    乾燥The filtrate was dried (MgSO4)
14. 14
    濃縮concentrated to dryness
15. 15
    その他An off-white solid was obtained
16. 16
    その他that was recrystallised
17. 17
    洗浄The filtered material was washed well with acetonitrile
18. 18
    その他dried (Vac/40° C.)

実験手順

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%.

出典