3-nitropyridine-2-sulfonyl chloride synthesis

Yield:-

Reaction Conditions:

with 1,3-dichloro-5,5-dimethylhydantoin;water;acetic acid in dichloromethane at 25; for 16 h;

Steps:

94 General Procedure 94: 3-Nitro-pyridine-2-sulfonyl chloride (Intermediate 445)

General Procedure 94: 3-Nitro-pyridine-2-sulfonyl chloride (Intermediate 445)AcOH (6 ml) and water (12 ml) were added to a solution of 2-benzylsulfanyl-3-nitro-pyridine 437 (3.0 g, 12.2 mmol) in DCM (42 ml) and the mixture was cooled to 0° C. A suspension of 1,3-dichloro-5,5-dimethyl-imidazolidine-2,4-dione (7.20 g, 36.58 mmol) in DCM (24 ml) was added portionwise to the vigorously stirring solution. The mixture was allowed to slowly warm to 25° C. and stirring was continued for 16 h. The mixture was poured into 5% aq. sodium metabisulfite solution (50 ml) and the aqueous phase was extracted with DCM (100 ml). The organic phase was washed with water, sat. NaHCO3 solution and brine, dried (Na2SO4) and concentrated in vacuo to give the title compound (2.7 g) which was used in the next step without further purification. The structure was confirmed by 1H NMR.

References:

US2012/214803,2012,A1 Location in patent:Page/Page column 170