Process for reacting fluorine-substituted heterocycles with amines in the presence of phase transfer catalysts

A process for preparing a compound of the formula (1a) or (1b) or (1c) ##STR13## where A is phenyl or phenyl substituted by 1 or 2 substituents selected from the group consisting of sulfo, carboxy, alkyl having from 1 to 4 carbon atoms, alkoxy having from 1 to 4 carbon atoms, chlorine, bromine, amino, alkylamino having from 1 to 4 carbon atoms in the alkyl group, sulfamoyl, carbamoyl and a fiber-reactive group from the vinyl sulfone series, said fiber-reactive group being bound directly by a covalent bond or via an alkylene group having from 1 to 4 carbon atoms or an alkylene-oxy-alkylene group having a total of 2 to 6 carbon atoms to the aromatic radical, or is trisulfonaphthyl or naphthyl or naphthyl substituted by 1 or 2 substituents selected from the group consisting of sulfo, carboxy, alkyl having from 1 to 4 carbon atoms, alkoxy having from 1 to 4 carbon atoms, amino, alkylamino having from 1 to 4 carbon atoms in the alkyl group, sulfamoyl, carbamoyl and a fiber-reactive group from the vinyl sulfone series, said fiber-reactive group being bound directly by a covalent bond or via an alkylene group having from 1 to 4 carbon atoms or an alkylene-oxy-alkylene group having a total of 2 to 6 carbon atoms to the aromatic-radical, or is the radical of a dye chromophore optionally containing a further amino group, which is selected from the group consisting of monoazo, disazo, copper, chromium and cobalt complex monoazo and disazo, anthraquinone, azomethine, phenazine, stilbene, triphenylmethane, xanthene, thioxanthene, nitroaryl, naphthoquinone, pyrenequinone, perylenetetracarbimide, formazane, copper formazane, phthalocyanine, copper phthalocyanine, nickel phthalocyanine, cobalt phthalocyanine, dioxazine or triphendioxazine dyes,

• R is hydrogen or alkyl having from 1 to 4 carbon atoms,
• G is an N atom or a group of the formula (a) ##STR14## where R.sup.o is hydrogen, halogen or cyano, X.sup.1 is hydrogen, halogen or a group of the formula (b) ##STR15## where R.sup.a has one of the meanings of R and A.sup.o has one of the meanings of A,
• X.sup.2 has one of the meanings of X.sup.1 and
• X.sup.3 has one of the meanings of X.sup.1,
• by reacting an amino compound of the formula (2) ##STR16## where A and R are as defined above, with a compound of the formula (3) ##STR17## where G, X.sup.1, X.sup.2 and X.sup.3 are as defined above and at least one of X.sup.1, X.sup.2 and X.sup.3 is fluorine,
• wherein the reaction is carried out in water or a mixture of water with an organic solvent which is immiscible or only partially miscible with water, in the presence of a phase transfer catalyst in an amount of from 0.1 to 10 mol %, based on the starting compound of the formula (2).