Water → HCID 20393335, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 34.6 g. of 5-chloro-2-methyl-3-phenylisoindole-1-carboxylic acid[ 2-(diethylamino)ethyl]-methylamide cyclohexanesulfamate in 400 ml. of water is treated with excess 2-N ammonium hydroxide. The liberated base is extracted with methylene chloride and the extract evaporated to dryness. To the obtained residue, there is added a solution of 86.4 g. of ceric ammonium nitrate in 150 ml. of water and 150 ml. of glacial acetic acid. The mixture is stirred at 80° C. for 20 minutes, the color of the solution obtained changing from orange to light yellow. After cooling, 750 ml. of ice-water are added and the separated oil is extracted with methylene chloride. The organic phase is washed with 2-N ammonium hydroxide and a saturated sodium chloride solution, dried over sodium sulfate and concentrated to dryness. o-benzoyl-p-chlorophenylglyoxylic acid[ 2-(diethylamino)ethyl]methylamide is obtained as an oil which can be used in the process without further purification. With 2 mols of N-cyclohexylsulfamic acid, the base forms an addition compound which melts at 136°-138° C. (decomposition) after crystallization from isopropanol/diethyl ether.

Provenance & Evidence