Water → N-((5-bromopyridin-3-yl)methylene)-2-methylpropane-2-sulfinamide

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-methyl-propane-2-sulfinamide (11 g, 91 mmol) and 5-bromo-3-pyridine-carboxaldehyde (14 g, 75 mmol) in dichloromethane (500 mL) is added titanium isopropoxide (43 g, 150 mmol). The reaction is then heated at reflux (bath temperature=60° C.) for 4 hours. The resultant mixture is cooled to room temperature and poured into a stirred mixture of diatomaceous earth (50 g) and water (150 mL). The slurry is stirred for 10 min and then filtered. The organic layer from the filtrate is washed with brine and dried over sodium sulfate. Filtration and concentration in vacuo affords 2-methyl-propane-2-sulfinic acid 1-(5-bromo-pyridin-3-yl)-methylideneamide as a yellow solid (22 g, 99%).

Provenance & Evidence