Reaktion #6255

Reaktionsgleichung

4-[3-(2-hydroxymethylbenzoyl)aminopropylthio]pyridine

triethylamine

methanesulfonyl chloride

→

desired compound

Ausbeute 78.9%

4-[3-(isoindolin-1-on-2-yl)propylthio]pyridine

Ausbeute 78.9%

Lösungsmittel

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe mixture was stirred at room temperature for 30 minutes
2. 2
   WaschenThe mixture was washed with saturated aqueous sodium bicarbonate, water and saturated saline
3. 3
   Trocknendried over anhydrous magnesium sulfate
4. 4
   workup.DISTILLATIONThe solvent was distilled off
5. 5
   Sonstigethe residue was purified by column chromatography (eluent: ethyl acetate)

Vorschrift

To a solution of 1.51 g (5.0 mmol) of 4-[3-(2-hydroxymethylbenzoyl)aminopropylthio]pyridine and 2.09 ml (15.0 mmol) of triethylamine in 50 ml of methylene chloride, 0.77 ml (10.0 mmol) of methanesulfonyl chloride was added with stirring at room temperature, and the mixture was stirred at room temperature for 30 minutes. The mixture was washed with saturated aqueous sodium bicarbonate, water and saturated saline, and dried over anhydrous magnesium sulfate. The solvent was distilled off and the residue was purified by column chromatography (eluent: ethyl acetate) to give 1.12 g of the desired compound (78.9% yield, pale brown crystals), mp. 73°-74.5° C.

Quelle