Реакция #409410

Уравнение реакции

sodium hydrogen carbonate

3-aminothiophenol

triethylamine

methyl 3-bromomethylthiophene-2-carboxylate

→

methyl 3-(3-aminophenylthiomethyl)thiophene-2-carboxylate

Выход 92.3%

Растворители

dichloromethane

Условия реакции

Обработка

1. 1
   Температураcooling
2. 2
   ПромывкаThe organic layer was washed successively with a saturated aqueous solution of sodium hydrogen carbonate
3. 3
   Сушкаa saturated aqueous solution of sodium chloride, and then dried over anhydrous magnesium sulfate
4. 4
   ФильтрацияAfter the drying agent was filtered off
5. 5
   Концентрированиеthe organic layer was concentrated under reduced pressure
6. 6
   ДругоеThe obtained oily substance was purified by silica gel column chromatography (hexane/ethyl acetate=7/1)

Методика

To a solution of 3-aminothiophenol (2.3 g, 18.7 mmol) and triethylamine (3.12 ml, 22.4 mmol) in dichloromethane (30 ml) was slowly added methyl 3-bromomethylthiophene-2-carboxylate (6.24 g, 22.4 mmol) under ice-cooling, followed by stirring for 30 minutes. After the reaction was completed, a saturated aqueous solution of sodium hydrogen carbonate was added to the reaction mixture. The organic layer was washed successively with a saturated aqueous solution of sodium hydrogen carbonate and a saturated aqueous solution of sodium chloride, and then dried over anhydrous magnesium sulfate. After the drying agent was filtered off, the organic layer was concentrated under reduced pressure. The obtained oily substance was purified by silica gel column chromatography (hexane/ethyl acetate=7/1) to give oily methyl 3-(3-aminophenylthiomethyl)thiophene-2-carboxylate (4.82 g, 92%).

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