tolonidine

Originator

Euctan,Essex,Switz.,1978

Definition

ChEBI: Tolonidine is a substituted aniline.

Manufacturing Process

43 g of the thiourea compound (melting point 124°C) obtained in known fashion from 2-chloro-4-methylaniline and ammonium thiocyanate and 20 cc of methyl iodide were dissolved in 200 cc of methanol, and the solution was refluxed for two hours.1 Thereafter, the solvent was evaporated in vacuo, leaving 73.2 g of the isothiouronium hydroiodide of the formula as a residue. This isothiouronium salt was admixed with 20 cc of ethylenediamine, and the mixture was heated for about 30 minutes at 150°C to 160°C, accompanied by stirring; methyl mercaptan escaped during that time. Subsequently, the reaction mixture was taken up in hot dilute acetic acid, and the resulting solution was made alkaline with 2 N sodium hydroxide. A precipitate formed, which was separated by vacuum filtration, washed with water and dried. It was identified to be 2-(2'-chloro-4'-methylphenyl)-amino-1,3- diazacyclopentene-(2) having a melting point of 142°C to 145°C. The yield was 10.2 g.
The nitrate of the base, obtained by acidifying a solution of the free base with nitric acid, had a melting point of 162°C to 164°C and was soluble in water and methanol.

Therapeutic Function

Antihypertensive