Phosphorus pentachloride → 1-Pentanesulfonyl chloride

To a solution of (4R)-4-[2,5-dichlorophenyl][4-chlorophenyl)sulfonyl]amino]pentylsulfonic acid (2.34 g, 4.80 mmol) in benzene (10 mL) was added phosphorus pentachloride (1.48 g, 7.21 mmol) at 22° C. The mixture was heated to reflux for 2 hours. This mixture was concentrated under reduced pressure and rediluted with CH2Cl2 (120 mL). This solution was washed with water (100 mL), dried over Na2SO4 and filtered. The organic solution was concentrated to afford 2.21 g of (4R)-4-[2, 5-dichlorophenyl][4-chlorophenyl)sulfonyl]-amino]pentylsulfonyl chloride as pale yellow oil in 91% yield. LC/MS 504.

1. temperatureThe mixture was heated
2. temperatureto reflux for 2 hours
3. concentrationThis mixture was concentrated under reduced pressure
4. additionrediluted with CH2Cl2 (120 mL)
5. washThis solution was washed with water (100 mL)
6. dry with materialdried over Na2SO4
7. filtrationfiltered
8. concentrationThe organic solution was concentrated

ORD record

ord-11857b598a394b76a1b8c4e97b7b43c7

Source dataset

uspto-grants-2005_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06967196B1