Reaction #51161

Reaction equation

Triethylamine

chloroform

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

bromoacetyl bromide

→

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

Yield 13.0%

Solvents

water

Conditions

Workup

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

Procedure

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.).

Source