反応 #51161

反応方程式

Triethylamine

chloroform

3-amino-2,4-bis(methylthio)-6-methylpyridine

bromoacetyl bromide

→

2-bromo-N-[2,4-bis(methylthio)-6-methyl-3-pyridyl]acetamide

収率 13.0%

溶媒

water

反応条件

後処理

1. 1
   workup.ADDITIONwas then slowly added
2. 2
   温度dropwise while being cooled with ice
3. 3
   抽出extracted with methylene chloride
4. 4
   洗浄The organic layer was washed with 1N hydrochloric acid, water
5. 5
   乾燥an aqueous solution of sodium hydrogencarbonate, water and a saturated aqueous solution of sodium chloride in this order, and dried over sodium sulfate
6. 6
   workup.DISTILLATIONSubsequently, the solvent was distilled off
7. 7
   その他the resulting crude product was purified through silica gel chromatography (silica gel 25 g, eluent-hexane:acetone=7:1→5:1→3:1)

実験手順

Triethylamine (274 mg, 2.71 mmol) was added to a chloroform (10 ml) solution of 3-amino-2,4-bis(methylthio)-6-methylpyridine (492 mg, 2.46 mmol), and bromoacetyl bromide (521 mg, 2.58 mmol) was then slowly added thereto dropwise while being cooled with ice. The mixture was stirred at room temperature for 2 hours. The reaction mixture was diluted with water, and then extracted with methylene chloride. The organic layer was washed with 1N hydrochloric acid, water, an aqueous solution of sodium hydrogencarbonate, water and a saturated aqueous solution of sodium chloride in this order, and dried over sodium sulfate. Subsequently, the solvent was distilled off, and the resulting crude product was purified through silica gel chromatography (silica gel 25 g, eluent-hexane:acetone=7:1→5:1→3:1) to obtain 100 mg (yield 13%) of 2-bromo-N-[2,4-bis(methylthio)-6-methyl-3-pyridyl]acetamide as a colorless crystal (melting point: 171 to 172° C.).

出典