Reaction of F-substituted triazine and pyrimidine compounds with amino compounds

摘要

Phase transfer catalysts are used to improve the yield and purity of products obtained from the reaction of amino compounds with F-substituted triazine and pyrimidine compounds. Compounds of formula (Ia), (Ib) or (Ic) are prepared by reacting an amino compound of formula (II) with a compound of formula (III), the reaction being carried out in water or a mixture of water and a solvent which is immiscible with or has only limited miscibility with water and in the presence of 0.1-10 mol. % on (II) of a phase transfer catalyst. A = phenyl; phenyl substituted by 1 or 2 substituents selected from sulfo, carboxy, 1-4C alkyl, 1-4C alkoxy, Cl, Br, amino, (1-4C)-alkylamino, sulfamoyl, carbamoyl and a fibre-reactive group of the vinylsulfone series bound to one of the aromatic residues by way of a 1-4C alkylene or an alkyloxyalkylene with a total of 2-6C; trisulfonaphthyl; naphthyl; naphthyl substituted by 1 or 2 substituents selected from sulfo, carboxy, 1-4C alkyl, 1-4C alkoxy, amino, (1-4C)-alkylamino, sulfamoyl, carbamoyl, and a fibre-reactive group of the vinylsulfone series bound to one of the aromatic residues by way of a 1-4C alkylene or an alkyloxyalkylene with a total of 2-6C; or the residue of a dye chromophore of the monoazo-, disazo-, Cu-, Cr- and Co-complex monoazo- and -disazo-, anthraquinone-, azomethine-, phenazine-, stilbene-, triphenylmethane-, xanthene-, thioxanthene-, nitroaryl-, naphthoquinone-, pyrenequinone-, perylenetetracarbimide-, formazan-, Cu formazan-, phthalocyanine-, Cu phthalocyanine-, Ni phthalocyanine-, Co phthalocyanine-, dioxazine- or triphendioxazine-series; R = H or 1-4C alkyl; G = an N atom or a group of formula -C(Ro)=; Ro = H, halogen or CN; X<1>-X<3> = H, halogen or a group of formula Ao-N(Ra)-; Ra = as for R; and Ao = as for A. A, R = as above; and G, X<1>, X<2> and X<3> = as above with the proviso that at least one of X<1>, X<2> and X<3> = F.