GB1103770A - Thioacrylic compounds and their preparation - Google Patents

Abstract

Thioacrylic compounds, some of which are novel, are prepared by contacting an N,N1-bis -(2-dithiocarboxyvinyl) derivative of a diamino compound (where hereinafter the term diamino refers to compounds having two primary or secondary amine groups or one of each) with an excess of a monoamino compound (where hereinafter the term monoamino refers to compounds containing one primary or secondary amino group) or a diamino compound; or contacting a 3-aminothioacrylamide in which the nitrogen atoms of the 3-amino and amide groups each carry at least one hydrocarbyl substituent, which whenever hereafter referred to may be substituted, or are hetero-atoms of heterocyclic rings or a 3-aminothioacrylic ester in which the nitrogen atom of the 3-amino group carries at least one hydrocarbyl group which may be substituted or is the heteroatom of a heterocyclic ring with excess diamine or a monoamine of the general formula R1R11NH in which R1 is H or a hydrocarbyl radical and R11 is a hydrocarbyl radical or R1 and R11 together with the nitrogen atom represents a heterocyclic ring provided that R1R11N- is not identical with the 3-amino group of the 3-aminothioacrylamide or 3-aminodithioacrylic ester. The 3-aminothioacrylic compound is preferably reacted with 2.5-25 times the stoichiometric quantity of amino compounds at a temperature in the range of 20-100 DEG C. The compounds of the following general formulae are prepared by the above process and are stated to be novel. <FORM:1103770/C2/1> wherein Z is H, CN or hydrocarbyl, R1 is H and R2 is a monocyclic aryl radical having a substituent ortho to the amino group. <FORM:1103770/C2/2> wherein R1 and R3 are H and R2 and R4 are different monocyclic aryl radicals or wherein R3\t is H, R2 and R4 are monocyclic aryl radicals and R1 is an alkyl radical. <FORM:1103770/C2/3> wherein R1 is H, R2 is a monocyclic aryl radical R4 and R5 are H or alkyl radicals and R6 is a divalent aliphatic or alicyclic or monocyclic aromatic radical or R4 and R5 and the nitrogen atoms to which they are bonded together with the radical R6 form a heterocyclic ring. <FORM:1103770/C2/4> wherein R1 is H, R2 is a monocyclic aryl radical R4 and R5 together with the nitrogen atoms to which they are bonded and the radical R6 form a heterocyclic ring, R9 is an alkylene radical and R10 is H or an alkyl radical. Specific compounds prepared by the above process are 3-p-toluidinothioacrylanilide, the corresponding ortho compound, methyl 3-anilinodithioacrylate and N,N1 - bis(2 - methylthiothiocarbonylvinyl)-piperazine.