Water → 5-Chloro-3-methyl-1,3-dihydro[1,2,5]thiadiazolo[3,4-b]pyridine 2,2-dioxide

Participants

Reaction Steps

To a round bottom flask was added 6-chloro-N2-methylpyridine-2,3-diamine (1-2) (2.043 g, 12.96 mmol), sulfamide (2.69 g, 28.0 mmol), and anhydrous pyridine (20 ml). The reaction mixture was refluxed at 125 C in a hot oil bath with stirring under an atmosphere of nitrogen with a water cooled reflux condenser attached overnight (16 hours). The reaction mixture was then cooled to room temperature and suspended in EtOAc (250 mL) & 6N HCl in water (250 mL) and filtered. Filtrate was then separated, organics dried over sodium sulfate, filtered & concentrated. The resulting residue was then purified with silica gel chromatography (0-20% Isopropanol/DCM) & concentrated to yield 5-chloro-3-methyl-1,3-dihydro[1,2,5]thiadiazolo[3,4-b]pyridine 2,2-dioxide (23-1). HRMS (M+H)+: observed=219.9946, calculated=219.9942.

Provenance & Evidence