Acetic Anhydride → HCID 18607002, compound

Participants

Reaction Steps

A mixture of 2.6 g of (±)-cis-2,3-dihydro-3-hydroxy-5-[3-(dimethylamino)propyl]-2-(4-methoxyphenyl)naphtho[1,2-b]-1,4-thiazepin-4(5H)-one hydrochloride and 25 mL of acetic anhydride was stirred and heated at 100° for 17 hours. The excess of reagent was removed under reduced pressure and the residue was dissolved in water. The aqueous solution was made basic with concentrated ammonium hydroxide and extracted with ethyl acetate (3×75 mL). The combined ethyl acetate solutions were washed with brine (50 mL) and dried (magnesium sulfate). Removal of the solvent gave 2.2 g (84%) (±)-cis-3-(acetyloxy)-2,3-dihydro-5-[3-(dimethylamino)propyl]-2-(4-methoxyphenyl)naphtho[1,2-b]-1,4-thiazepin-4(5H)-one. A sample of this compound was crystallized from ether, mp 98°-99°.

Provenance & Evidence