Ammonium Hydroxide → 6-chloropyridine-3-sulfonamide

6-chloropyridine-3-sulfonyl chloride (4.1 g, 19.3 mmol) was stirred in ammonium hydroxide (30 mL) at room temperature for 2 hr. The reaction mixture was diluted with EtOAc (150 mL) and any insoluble material filtered. The filtrate was transferred to a separatory funnel and the phases were separated. The aqueous phase was further extracted with EtOAc (1×15 mL). The combined EtOAc extractions were washed with H2O (1×50 mL), saturated NaCl (1×50 mL), dried (Na2SO4), and concentrated in vacuo to give 6-chloropyridine-3-sulfonamide (2.58 g, 69%). MS (EI) for C5H3Cl2NO2S: 190.9 (MH−).

1. filtrationany insoluble material filtered
2. customThe filtrate was transferred to a separatory funnel
3. customthe phases were separated
4. extractionThe aqueous phase was further extracted with EtOAc (1×15 mL)
5. extractionThe combined EtOAc extractions
6. washwere washed with H2O (1×50 mL), saturated NaCl (1×50 mL)
7. dry with materialdried (Na2SO4)
8. concentrationconcentrated in vacuo

ORD record

ord-d0a5d626b1514eddb4af7c93484118c7

Source dataset

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08642584B2