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

Temperature

0 °C

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.

1. customInto a 250 mL round bottom flask was placed
2. customto react
3. customthe ice bath was removed
4. customto react for an additional 25 minutes at room temperature
5. washThe resulting mixture was washed 2 times with 50 mL of NaHSO3 and 2 times with 50 mL of brine
6. dry with materialThe mixture was dried over Na2SO4
7. concentrationconcentrated by evaporation under vacuum
8. customa rotary evaporator
9. customThe residue was purified
10. washby eluting through a column with a 2:3 ethyl acetate/petroleum ether solvent system
11. customThis resulted in 6.6 g (82.5%) of 3-(3-methoxypyrrolidin-1-yl)benzene-1-sulfonyl chloride as yellow oil

ORD record

ord-049fd5fd7b704f56b84e14b62e715c66

Source dataset

uspto-grants-2010_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07696229B2