Reaktion #51161

Reaktionsgleichung

Triethylamine

chloroform

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

bromoacetyl bromide

→

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

Ausbeute 13.0%

Lösungsmittel

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas then slowly added
2. 2
   Temperaturdropwise while being cooled with ice
3. 3
   Extraktionextracted with methylene chloride
4. 4
   WaschenThe organic layer was washed with 1N hydrochloric acid, water
5. 5
   Trocknenan 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
   Sonstigethe resulting crude product was purified through silica gel chromatography (silica gel 25 g, eluent-hexane:acetone=7:1→5:1→3:1)

Vorschrift

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.).

Quelle