Chlorosuccinimide → 3-(3-Methoxy-1-pyrrolidinyl)benzenesulfonyl chloride

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

Into a 250 mL round bottom flask was placed a solution of lithium 3-(3-methoxypyrrolidin-1-yl)benzenesulfinate (12 g, 29.15 mmol) in dichloromethane (100 mL). To the above was added NCS (4.48 g, 33.56 mmol) in several batches, while cooling to a temperature of 0° C. over a time period of 10 minutes. The resulting solution was allowed to react, with stirring, for 15 minutes while the temperature was maintained at 0° C. in a bath of H2O/ice, then the ice bath was removed and the solution was allowed to react for an additional 25 minutes at room temperature. The reaction progress was monitored by TLC (ethyl acetate/petroleum ether 5=1:1). The resulting mixture was washed 2 times with 50 mL of NaHSO3 and 2 times with 50 mL of brine. The mixture was dried over Na2SO4 and concentrated by evaporation under vacuum using a rotary evaporator. The residue was purified by eluting through a column with a 2:3 ethyl acetate/petroleum ether solvent system. This resulted in 6.6 g (82.5%) of 3-(3-methoxypyrrolidin-1-yl)benzene-1-sulfonyl chloride as yellow oil.

Herkunft & Nachweise