Process for the preparation of 4-amino-6-tert.-butyl-...

Details Process for the preparation of 4-amino-6-tert.-butyl-... Process for the preparation of 4-amino-6-tert.-butyl-...

C - Chemistry, Metallurgy

07

D

260/248.6

C07D 253/06 (2006.01) C07D 253/075 (2006.01)

Patent

CA 1148542

ABSTRACT In the preparation of 4-amino-6-tert.-butyl-3- methylthio-1,2,4-triazin-5-(4H)-one of the formula Image wherein pivaloyl cyanide of the formula (CH3)3C-CO-CN is reacted to form an intermediate, the intermediate is condensed with thiocarbohydrazide of the formula NH2-NH-CS-NH-NH2 to form 4-amino-6-tert.-butyl-3-mercapto-1,2,4-triazin-5-(4H)- one of the formula Image and the 4-amino-6-tert.-butyl-3-mercapto-1,2,4-triazin-5(4H)- one is alkylated to replace the H atom on the sulphur by -C1-4- alkyl, the improvement which comprises reacting the pivaloyl cyanide with a carboxylic acid anhydride of the formula R-CO-O-CO-R in which R is an optionally substituted allphatic radical with up to 8 carbon atoms or an optionally substituted phenyl radical, in the presence of a strong acid at a temperature between about -50 and +150°C, and then directly reacting the reaction mix- ture thus obtained with the thiocarbahydrazide. Advantageously R is CH3, the strong acid is concentrated sulphuric acid, the pivaloyl cyanide is effected at a temperature between about 0 and 100°C, the condensation with thiocarbohydrazide is effected, in the presence of a mineral acid, in an aqueous or aqueous-alcoholic medium, and the alkylation is effected using methyl iodide or methyl bromide in the presence of sodium hydroxide at about 0 to 50C.

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