HCID 20450000, compound → HCID 20450013, compound

Participants

Reaction Steps

93.1 g of 8-(ethoxycarbonylamino)-6-(2-chlorophenyl)-1,3,4,6-tetrahydro-2-oxo-2H-5,1-benzothiazocine 5,5-dioxide are dissolved at 80° in a mixture of 1.3 l of carbon tetrachloride, 1.3 l of t-butanol and 33.5 ml of water. After cooling to 35°, the mixture is treated rapidly with 212 g of potassium t-butylate (in three portions) while cooling strongly. The temperature thereby rises to 45°-50°. After the reaction has faded away, the cooling bath is removed and the mixture is stirred for a further 30 minutes. The mixture is poured on to ice and extracted several times with chloroform. The organic solvents are evaporated and the residue is chromatographed on 310 g of silica gel. The desired product is eluted with toluene/chloroform (1:3). After recrystallization from ethyl acetate/petroleum ether, there is obtained ethyl 5-(2-chlorophenyl)-2,3-dihydro-2-oxo-1H-1-benzazepine-7-carbamate of melting point 241°.

Provenance & Evidence