Diethyl Ether → HCID 86682577, compound

Participants

Reaction Steps

To an ice cooled solution of 3-((1H-pyrrol-1-yl)methyl)pyridine (2.94 g, 18.58 mmol) in 25 mL of dry methylene chloride was added drop wise to O-mesitylenesulfonylhydroxylamine (4.0 g, 18.58 mmol) in 10 mL of dry methylene chloride over 5 min with stirring. The reaction was stirred at 0° C. for 3 hrs. 60 mL of ether was added and the suspension filtered. The precipitate was recrystallized from ethyl acetate-methanol (5:1 v/v) to give 3-((1H-pyrrol-1-yl)methyl)-1-aminopyridinium mesitylenesulfonate (8) in 57.5% yield. The N-Aminopyridinium salt (1.5 g, 4.02 mmol) in 30 ml of anhydrous tetrahydrofuran (THF) containing triethylamine at 70° C. was stirred for 5 min before benzenesulfonyl chloride (0.78 g, 4.42 mmol) was added. The mixture was allowed to proceed for 12 hrs. 70 mL of saturated sodium bicarbonate (NaHCO3) arrested the reaction. The product (10a) was extracted twice with 100 ml of chloroform and dried over anhydrous sodium sulfate, followed by filtration. Solvent was removed in vacuo to give the crude product, which was further purified by column chromatography (2.5×22 cm) on silica gel (200-425 mesh) using ethyl acetate:methanol (9:1 v/v) as eluent. The resultant product was obtained as a light yellow crystalline solid in 43.9% yield.

Provenance & Evidence