p-Toluenesulfonic acid monohydrate → HCID 58513608, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of N-{5-bromo-2-[(cyclopropylmethyl)amino]phenyl}-3,3-dimethylbutanamide (Step C, 11.2 g, 33.0 mmol), p-toluenesulfonic acid monohydrate (6.29 g, 33.0 mmol) and toluene (240 mL) was stirred at reflux temperature for 20 h with Dean-Stark apparatus. The mixture was cooled to 0° C. The resulting precipitate was collected by filtration and washing with small amount of ethyl acetate. The residue was dissolved in ethyl acetate (200 mL). The whole was extracted with saturated sodium hydrogen carbonate aqueous solution (100 mL). The organic layer was washed with brine (20 mL), dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=3:1 as eluent) to give the title compound (10.1 g, 95%) as a white solid.

Provenance & Evidence