Dimercapto triazoles
A process for the preparation of 3.5-dimercapto-1,2,4-triazole of the following tautomeric formulae wherein R represents H, alkyl, alkenyl, aralkyl or aryl comprises heating a hydrazodithiodicarbonamide of the formula wherein R is defined as above and R1 is H or C1- 6 alkyl or alkenyl, with an aqu...
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Zusammenfassung: | A process for the preparation of 3.5-dimercapto-1,2,4-triazole of the following tautomeric formulae wherein R represents H, alkyl, alkenyl, aralkyl or aryl comprises heating a hydrazodithiodicarbonamide of the formula wherein R is defined as above and R1 is H or C1- 6 alkyl or alkenyl, with an aqueous solution of a group IB metal hydroxide using between 1-6 equivalents of hydroxide per mole of hydrazodithiodicarbonamide, the strength of the solution being 0.2-2.0 N hydroxide, or by heating with an aqueous solution of a strong organic base. The dimercapto triazoles are claimed per se when R is alkyl or aralkyl. In preferred embodiments of the invention, 2-3 equivalent of hydroxide are used at 0.5-1.0 N strength, with a reaction time of 24 hours heating under reflux. When R in the product is to be H or C1- 6 alkyl, then the groups R and R1 in the starting material are preferably the same. 3 - Amino - 5 - mercaptotriazoles are produced as a by-product in this reaction, for example 3 - amino - 5 - mercapto - 1,2,4 - triazole. The desired product is recovered by recrystallization from water, or by dissolution in Na2CO3 solution, followed by solvent extraction of the aforementioned by-product, and finally liberation of the required 3,5-dimercaptotriazole by acidification. |
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