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) and saturated NaCl (1×50 mL), dried over Na2SO4, and concentrated in vacuo to give 6-chloropyridine-3-sulfonamide (2.58 g, 69%). MS (EI) m/z for C5H5Cl2N2O2S: 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) and saturated NaCl (1×50 mL)
7. dry with materialdried over Na2SO4
8. concentrationconcentrated in vacuo

ORD record

ord-032c98dcdd4f4677857c3d9ed3d75790

Source dataset

uspto-grants-2011_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07989622B2