Ethyl chloroformate → HCID 18606997, compound

Participants

Reaction Steps

To a solution of 0.8 g of (±)-cis-2,3-dihydro-3-hydroxy-2-(4-methoxyphenyl)-5-[2-(dimethylamino)ethyl]naphtho[1,2-b]-1,4-thiazepin-4(5H)-one in 10 mL of pyridine (dried over potassiuwm hydroxide) in an ice-bath, 0.4 g of ethyl chloroformate was added dropwise then stored in the freezer overnight. The mixture was concentrated under reduced pressure and the residue was partitioned between ether and dilute sodium hydroxide. The ether solution was washed with brine then dried (magnesium sulfate) and removal of the solvent gave 0.9 g (97%) of (±)-cis-3-[(ethoxycarbonyl)oxy]-2,3-dihydro-2-(4-methoxyphenyl)-5-[2-(dimethylamino)ethyl]naphtho[1,2-b]-1,4-thiazepin-4(5H)-one. A sample was crystallized from ether--pet. ether, mp 168°-169°.

Provenance & Evidence