Reaction #51162

Reaction equation

Triethylamine

THF

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

4-bromobutanoyl chloride

→

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

Yield 66.0%

Solvents

water

Conditions

Workup

1. 1
   workup.ADDITIONwas then slowly added
2. 2
   Temperaturedropwise while being cooled with ice
3. 3
   Extractionextracted with ethyl acetate
4. 4
   WashThe organic layer was washed with water
5. 5
   Dryingwith a saturated aqueous solution of sodium chloride, 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 75 g, eluent-hexane:acetone=5:1→3:1)

Procedure

Triethylamine (206 mg, 2.04 mmol) was added to a THF (6 ml) solution of 3-amino-2,4-bis(methylthio)-6-methylpyridine (341 mg, 1.70 mmol), and 4-bromobutanoyl chloride (379 mg, 2.04 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 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:acetone=5:1→3:1) to obtain 390 mg (yield 66%) of 4-bromo-N-[2,4-bis(methylthio)-6-methyl-3-pyridyl]butanamide as a colorless crystal (melting point: 139 to 140° C.).

Source