Hydrochloric Acid → N-[3-(4-fluoro-2-nitrophenoxy)propyl]methansulfonamide

Pyridine (1.5 ml, 18.6 mmol) and methanesulfonyl chloride (0.8 ml, 10.3 mmol) were added, while being cooled with ice, to a dichloromethane solution of 3-(4-fluoro-2-nitrophenoxy)propylamine (2.0 g, 9.33 mmol), and dichloromethane (4 ml) was further added. The resulting mixture was stirred at room temperature for 24 hours, and methanesulfonyl chloride (0.12 ml, 1.5 mmol) was further added thereto, and then the mixture was stirred at room temperature for 15 hours. 2N hydrochloric acid (9.5 ml) was added to the reaction mixture, and the mixture was stirred. Water was added to the mixture, and the resulting mixture was extracted with dichloromethane. After being washed with a saturated sodium chloride aqueous solution, the organic layer was concentrated under reduced pressure, and the residue was then purified by silica gel column chromatography (n-hexane:ethyl acetate=4:1→1:1). The purified product was concentrated under reduced pressure to thereby obtain 1.2 g of oily yellow orange N-[3-(4-fluoro-2-nitrophenoxy)propyl]methansulfonamide (yield: 44%).

1. additionwas further added
2. stirringthe mixture was stirred at room temperature for 15 hours
3. stirringthe mixture was stirred
4. extractionthe resulting mixture was extracted with dichloromethane
5. washAfter being washed with a saturated sodium chloride aqueous solution
6. concentrationthe organic layer was concentrated under reduced pressure
7. customthe residue was then purified by silica gel column chromatography (n-hexane:ethyl acetate=4:1→1:1)
8. concentrationThe purified product was concentrated under reduced pressure

ORD record

ord-09cc70b3ad4d48839a2d1c25e87060d8

Source dataset

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08642619B2