Реакция #83375

Уравнение реакции

4-aminothiophenol

4-Aminothiophenol

sodium hydride

Water

2-Chloropyridine

→

2-(4-aminophenylthio)pyridine

Выход 10.0%

Растворители

DMF

Условия реакции

Обработка

1. 1
   Промывкаpreviously washed with hexane)
2. 2
   workup.STIRRINGthe reaction stirred at room temperature for 16 hr
3. 3
   Экстракцияthe product extracted with ethyl acetate
4. 4
   ПромывкаThe solution was washed thoroughly with water
5. 5
   Сушкаdried over sodium sulfate
6. 6
   Концентрированиеconcentrated
7. 7
   ДругоеThe product was purified by HPLC over silica gel
8. 8
   Промывкаeluted with 30% ethyl acetate/hexane

Методика

4-Aminothiophenol (0.065 moles, 8.1 g) in 275 ml DMF was stirred at room temperature for 1 hr with sodium hydride (0.065 moles previously washed with hexane). 2-Chloropyridine (0.06 moles, 6.8 g) was added and the reaction mixture was stirred for 6 hr. An additional 5.2 g of 4-aminothiophenol was added and the reaction stirred at room temperature for 16 hr. Water was added and the product extracted with ethyl acetate. The solution was washed thoroughly with water, dried over sodium sulfate and concentrated. The product was purified by HPLC over silica gel eluted with 30% ethyl acetate/hexane to yield 2-(4-aminophenylthio)pyridine 1.2 g, 10%. Mass spec (FD) 202. Calculated for C11H10N2S: C, 65.32; H, 4.98, N, 13.85 Found: C, 65.23; H, 5.09; N, 13.63.

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