反応 #51160

反応方程式

Triethylamine

chloroform

3-amino-6-methyl-2-methylthiopyridine

water

chloroform

9-bromononanyl chloride

→

9-bromo-N-(6-methyl-2-methylthio-3-pyridyl)nonanamide

収率 27.0%

反応条件

後処理

1. 1
   温度dropwise while being cooled with ice
2. 2
   抽出extracted with ethyl acetate
3. 3
   洗浄The organic layer was washed with water
4. 4
   乾燥with a saturated aqueous solution of sodium chloride, and dried over sodium sulfate
5. 5
   workup.DISTILLATIONSubsequently, the solvent was distilled off
6. 6
   その他the resulting crude product was purified through silica gel chromatography (silica gel 75 g, eluent-hexane:ethyl acetate=10:1→4:1)

実験手順

Triethylamine (607 mg, 6.0 mmol) was added to a chloroform (10 ml) solution of 3-amino-6-methyl-2-methylthiopyridine (685 mg, 4.44 mmol), and a chloroform (3 ml) solution of 9-bromononanyl chloride (1,281 mg, 5 mmol) was then slowly added thereto dropwise while being cooled with ice. The mixture was stirred at room temperature for 17 hours. The reaction mixture was diluted with water, and then extracted with ethyl acetate. The organic layer was washed with water and then with a saturated aqueous solution of sodium chloride, and dried over sodium sulfate. Subsequently, the solvent was distilled off, and the resulting crude product was purified through silica gel chromatography (silica gel 75 g, eluent-hexane:ethyl acetate=10:1→4:1) to obtain 433 mg (yield 27%) of 9-bromo-N-(6-methyl-2-methylthio-3-pyridyl)nonanamide as a colorless crystal (melting point: 80 to 82° C.).

出典