Реакция #2267058

Уравнение реакции

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

Растворители

ethyl acetate

Условия реакции

Обработка

1. 1
   ТемператураThe mixture was heated
2. 2
   Температураto reflux
3. 3
   Температураat reflux over night
4. 4
   ТемператураAs the mixture warmed the cream suspension
5. 5
   workup.DISSOLUTIONgradually dissolved
6. 6
   ТемператураJust before refluxing
7. 7
   Другоеformed
8. 8
   Фильтрацияfiltered
9. 9
   Промывкаthe residue was washed well with ethanol
10. 10
    КонцентрированиеThe resulting filtrate was concentrated to dryness
11. 11
    Другоеto give an off-white solid
12. 12
    Промывкаwashed with 1) water (800 mL) and 2) brine (1 L)
13. 13
    СушкаThe filtrate was dried (MgSO4)
14. 14
    Концентрированиеconcentrated to dryness
15. 15
    ДругоеAn off-white solid was obtained
16. 16
    Другоеthat was recrystallised
17. 17
    ПромывкаThe filtered material was washed well with acetonitrile
18. 18
    Другоеdried (Vac/40° C.)

Методика

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%.

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