Tert-Butanesulfinamide → N-[(3-bromophenyl)(2-cyanophenyl)methylene]-2-methylpropane-2-sulfinamide

Participants

Reaction Conditions

Reaction Steps

To a solution of titanium (IV) ethoxide (3.48 g, 15.3 mmol) in tetrahydrofuran (14.0 mL) was added 3-bromo-2′-cyanobenzophenone (2.00, 7.0 mmol). After stirring for two minutes, 2-methyl-2-propanesulfinamide (0.93 g, 7.68 mmol) was added. The mixture was refluxed for 13 hours and heated at 50° C. for 31 hours. After cooling to ambient temperature, the mixture was diluted with methanol (15 mL) and treated with saturated aqueous sodium bicarbonate solution (15 drops) to form a gelatinous precipitate. The material was further diluted with ethyl acetate and vacuum filtered through a pad of sodium sulfate to remove the precipitate. The filtrate was concentrated to a crude oil that was purified by flash chromatography on silica gel with 10% acetonitrile/dichloromethane and triturated with hexane/ethyl acetate to give the title compound as a yellow solid (1.81 g, 66%). 1H NMR (300 MHz, DMSO-d6) δ 7.98 (d, J=7.7 Hz, 1 H), 7.87-7.79 (m, 2 H), 7.72-7.66 (m, 2 H), 7.64-7.43 (m, 3 H), 1.27 (s, 9 H).

Provenance & Evidence