Certain 3-phenylhydrazono-2-amino-1,1,3-propene tricarbonitrile
AssigneeCiba-Geigy Corporation
InventorRobert Portmann
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Abstract
The invention relates to a process for the preparation of azo dyes of the formula ##STR1## or mixtures thereof, in which Ar is a substituted or unsubstituted phenyl, naphthyl or aromatic heterocyclic radical and Y is a group of the formula --O--R, --S--R or ##STR2## in which R is a substituted or unsubstituted alkyl, aryl or heterocyclic radical and R.sub.1 and R.sub.2 independently of one another are hydrogen or a substituted or unsubstituted alkyl, aryl or heterocyclic radical, and the groups R.sub.1 and R.sub.2, together with the nitrogen atom to which they are bonded, can form a ring. The process comprises first coupling dimeric malonodinitrile with a diazo component and cyclizing the resulting intermediate with an alcohol, thioalcohol or amine.
Claims3
A compound of the formula ##STR52## in which Ar is a substituted or unsubstituted phenyl radical or a naphthyl radical wherein the substituents are one or more halogen atoms or nitro, cyano, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, m- or p-carboxyl, aryloxy, C.sub.1 -C.sub.4 -alkoxycarbonyl, sulfonamide, carboxamide, acyl, acylamino or phenylazo groups, and the phenyl nucleus in the phenylazo groups can be substituted by chlorine, nitro, cyano, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkoxycarbonyl or sulfonamide groups.
A compound of the formula ##STR53## in which Ar.sub.2 is a phenyl radical, which can carry one or more halogen atoms or nitro, cyano, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, m- or p-carboxyl, aryloxy, C.sub.1 -C.sub.4 -alkoxycarbonyl, sulfonamide, carboxamide, acyl, acylamino or phenylazo groups, and the phenyl nucleus in the phenylazo groups can be substituted by chlorine, nitro, cyano, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkoxycarbonyl or sulfonamide groups.
A compound of the formula ##STR54## in which Ar.sub.3 is a phenyl radical or a 4-nitrophenyl, 2-chloro-4-nitrophenyl, 2-cyano-4-nitrophenyl, 2,4-dinitrophenyl, 2-chloro-4,6-dinitrophenyl or 3- or 4-carboxyphenyl radical.
Dependencies are inferred from the claim text.