Dimethylformamide → 7-bromo-N-[4-[[N-methyl-N-(tetrahydropyran-4-yl)amino]methyl]phenyl]-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxamide

Participants

Reaction Steps

To a suspension of 7-bromo-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylic acid (4.47 g) in THF (90 ml) were added at room temperature thionyl chloride (1.03 ml) and DMF (1 ml), and the mixture was stirred for 1 hour and added dropwise to a solution of 4-[[N-methyl-N-(tetrahydropyran-4-yl)amino]methyl]aniline (3.41 g) and triethylamine (7.9 ml) in THF (30 ml), at 0° C. The mixture was stirred for 3 hours and concentrated under reduced pressure, to which were added water. Precipitated colorless crystals were collected by filtration, and the crystals were washed with water, ethanol, 2-propanol and diisopropylether to give colorless crystals of 7-bromo-N-[4-[[N-methyl-N-(tetrahydropyran-4-yl)amino]methyl]phenyl]-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxamide (4.94 g).

Provenance & Evidence