Ammonium Hydroxide → 2-Amino-5-bromopyridine-3-sulfonamide

To a solution of chlorosulfonic acid (20 mL) at 0° C. was added 2-amino-5-bromopyridine (5.0 g, 0.029 mmol) portion wise. Upon completion of addition, the reaction mixture was heated to reflux where it stirred for 16 h. After this time, the reaction mixture was allowed to cool to RT. Once at the prescribed temperature, the reaction mixture was poured drop wise in to an aqueous ammonium hydroxide solution. The resulting mixture was extracted with ethyl acetate. The combined organic portions were washed with a brine solution, dried over Na2SO4 and concentrated under reduced pressure to yield 2-amino-5-bromopyridine-3-sulfonamide (4.7 g, 65%), which was used without further purification. LCMS Method Y: retention time 0.5 min, [M−1]=250.8.

1. additionUpon completion of addition
2. temperaturethe reaction mixture was heated
3. temperatureto reflux where it
4. extractionThe resulting mixture was extracted with ethyl acetate
5. washThe combined organic portions were washed with a brine solution
6. dry with materialdried over Na2SO4
7. concentrationconcentrated under reduced pressure

ORD record

ord-14f21f08076c416d91127b1750f14939

Source dataset

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08575184B2