Reaction #51160

Reaction equation

Triethylamine

chloroform

3-amino-6-methyl-2-methylthiopyridine

water

chloroform

9-bromononanyl chloride

→

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

Yield 27.0%

Conditions

Workup

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

Procedure

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.).

Source