Реакция #1859304

Уравнение реакции

methanol

116c

Methyl 3-(Bromomethyl)thiophene-2-carboxylate

ammonia

→

116d

Выход 57.0%

Methyl 3-(Aminomethyl)thiophene-2-carboxylate

Выход 57.0%

Условия реакции

Обработка

1. 1
   ДругоеA 2-L single-neck round-bottomed flask equipped with a magnetic stirrer and nitrogen inlet
2. 2
   Другоеwas purged with nitrogen
3. 3
   КонцентрированиеAfter that time, the reaction mixture was concentrated under reduced pressure
4. 4
   workup.DISSOLUTIONThe residue was dissolved in water (150 mL)
5. 5
   Экстракцияextracted with methyl tert-butyl ether (2×25 mL)
6. 6
   Экстракцияextracted with methyl tert-butyl ether (3×150 mL)
7. 7
   СушкаThe combined organic layers were dried over sodium sulfate
8. 8
   Концентрированиеconcentrated under reduced pressure

Методика

A 2-L single-neck round-bottomed flask equipped with a magnetic stirrer and nitrogen inlet was purged with nitrogen and charged with 116c (7.50 g, 32.0 mmol) and a 7 M solution of ammonia in methanol (915 mL, 6.40 mol). The solution was stirred at room temperature for 14 h. After that time, the reaction mixture was concentrated under reduced pressure. The residue was dissolved in water (150 mL) and extracted with methyl tert-butyl ether (2×25 mL). The aqueous layer was basified with sodium hydroxide (5.00 g) and extracted with methyl tert-butyl ether (3×150 mL). The combined organic layers were dried over sodium sulfate and concentrated under reduced pressure to afford a 57% yield (3.14 g) of 116d as a colorless oil: 1H NMR (300 MHz, CDCl3) δ 7.45 (d, 1H, J=5.1 Hz), 7.14 (d, 1H, J=5.1 Hz), 4.11 (s, 2H), 3.88 (s, 3H), 1.72 (br s, 2H); MS (ESI+) m/z 172.0 (M+H). The material was used without further purification.

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