ChemInform Abstract: DARST. VON 1,3‐BIS‐(ALKYLMERCAPTO)‐ISOTHIAZOLEN

Abstract

Bei der Alkylierung des Bis‐Na‐mercaptids (I) mit den Alkyljodiden (II) erfolgt zunächst ein Angriff auf die 3‐S‐Funktion unter Bildung der Derivate (III), die durch weitere Umsetzung mit entsprechenden Alkyljodiden in 3,5‐Bis‐sulfide von Typ (IV) übergeführt werden.

Novel Synthesis of cis-Nickel(II) 3-Alkylimino-3-alkyl(or aryl)thio-1-arylpropenethiolates and Their Application to the Preparation of 5-Aryl-3-(arylthio)isothiazoles

“…For instance, 4-cyano-3,5-(dimethylthio)isothiazole was prepared by treatment of 2-cyanoethylthioamide with a hydroxide base in carbon disulfide, followed by addition of iodomethane and iodine in sequence . Alternatively, the reaction of the disodium salt of 4-cyano-3,5-(dimercapto)isothiazole (readily available from dicyanoethylenedithiolate and sulfur) with alkyl halides afforded 4-cyano-3,5-(dialkylthio)isothiazoles . Treatment of 3,5-dichloro-4-cyanoisothiazole with sodium sulfide in the presence of iodomethane also led to the foregoing isothiazole derivatives. ,6c However, the latter reaction was accompanied by ring cleavage.…”

“…Alternatively, the reaction of the disodium salt of 4-cyano-3,5-(dimercapto)isothiazole (readily available from dicyanoethylenedithiolate and sulfur) with alkyl halides afforded 4-cyano-3,5-(dialkylthio)isothiazoles . Treatment of 3,5-dichloro-4-cyanoisothiazole with sodium sulfide in the presence of iodomethane also led to the foregoing isothiazole derivatives. ,6c However, the latter reaction was accompanied by ring cleavage. The other method involves the thermal elimination of sulfur from 1,4,2-dithiazines, yielding 3-(methylthio)isothiazoles along with other products .…”