Triethylamine → HCID 12790641, compound

Participants

Reaction Steps

To a solution of N-(diethylaminoethyl)-5-amino 4-chloro-2-methoxybenzamide (1.1 g) and triethylamine (815 mg) in dry methylene chloride (11 ml) is added dropwise a solution of methanesulfonyl chloride (882 mg) in dry methylene chloride (5ml) under ice-cooling and stirring and the resultant mixture is stirred at room temperature for 30 minutes. The reaction mixture is mixed with aqueous sodium hydrogen-carbonate and the methylene chloride layer is separated. The organic layer is washed with water, dried over anhydrous sodium sulfate and concentrated. The intermediary N-(diethylaminoethyl)-5-bis(methanesulfonyl)amino-4-chloro-2-methoxybenzamide obtained as a residue is mixed with 10 % aqueous sodium hydroxide (18ml) and methanol (2 ml) and heated at 50° C. for 30 minutes. The reaction mixture is acidified with conc. hydrochloric acid, neutralized with aqueous sodium hydrogencarbonate, salted out with brine, and shaken with methylene chloride. The organic layer is dried over anhydrous sodium sulfate, and concentrated. The residue is chromatographed on a column of alumina, which is eluted with methylene chloride. The eluate is concentrated and the residue is washed with ethyl acetate - isoproyl ether to give N-(diethylaminoethyl)-4-chloro-5-methanesulfonamido-2-methoxybenzamide (993 mg) as crystals melting at 123° to 123.5° C.

Provenance & Evidence