GB1099058A - Thioacrylic compounds and their preparation - Google Patents

Abstract

Novel compounds of the general formulae <FORM:1099058/C2/1> and <FORM:1099058/C2/2> and its amine salts with HNR1R2 and metal salts, wherein in Formula I when R1 and R3 are H, R2 and R4 are the same monocyclic aryl radicals with no substituents ortho to the amino group, or in which R1 and R3 are H or alkyl radicals and R2 and R4 are the same aralkyl radical or in which R1 represents H or an alkyl radical, R2 is an alkyl or cyclo-alkyl radical, R3 is H or an alkyl radical and R4 is an alkyl or cycloalkyl radical or, when R3 is H, a monocyclic aryl group in which there are no substituents ortho to the amino group, or an aralkyl radical, or in which R1 is H or an alkyl radical and R2 is an alkyl or cycloalkyl radical and R3 and R4 together represent a divalent radical which, together with the nitrogen atom to which it is bonded forms a heterocyclic ring or in which R1 and R2 together represent a divalent radical which together with the nitrogen atom to which it is bonded forms a heterocyclic ring, R3 is H or alkyl, R4 is alkyl or cycloalkyl or, when R3 is H, a monocyclic aryl radical in which there are no substituents ortho to the amino group or an aralkyl radical, or R3 and R4 together represent a divalent radical which together with the nitrogen atom to which it is bonded forms a heterocyclic ring and in Formula II R1 is H or alkyl, R2 is alkyl or cycloalkyl or R1 and R2 together represent a divalent radical which together with the nitrogen atom to which it is bonded forms a heterocyclic ring, are prepared inter alia by a process for the preparation of a thioarylamide by heating trithione with an aromatic monocyclic primary amine in which there are no substituents ortho to the amino group or an aralkyl primary or secondary amine, by a process for the preparation of an amine salt of a dithioacrylic acid by contacting trithione with an aliphatic prmary or secondary amine or an alicyclic primary amine or a N-alkyl alicyclic secondary amine or a heterocyclic secondary amine in which the nitrogen of the amino group forms part of the heterocyclic ring, optionally converting the amine salt into the free dithioacrylic acid, optionally treating the free acid with an aliphatic primary amine or secondary amine, or an alicyclic primary amine, or a N-alkyl aliphatic secondary amine, or an aralkyl primary amine, or an aromatic monocyclic primary amine in which there are no substituents ortho to the amino group or a heterocyclic secondary amine in which the nitrogen atom forms part of the heterocyclic ring to form a thioacrylamide.