Procedure for preparation of compounds with the general formula 1, which
include the racemic mixtures ()-1, and the enantiomerically pure compounds
(-)-1 and (+)-1, wherein R1 and R3, like or different, represent
an atom of hydrogen, chlorine, fluorine, a methyl, trifluoromethyl or methoxy group;
R2 represents an atom of hydrogen, chlorine, fluorine, a methyl, trifluoromethyl,
methoxy, trifluoromethoxy, methylsulphonyl or aminosulphonyl group; R4 represents
an atom of hydrogen, chlorine, fluorine, a methyl, trifluoromethyl, methoxy, trifluoromethoxy,
methylsulphonyl or aminosulphonyl group, with the condition that one of the substituents
R2 or R4 is a methylsulphonyl or aminosulphonyl group; which
involves obtaining the racemic mixture with the general formula ()-1 by reacting
an (E)-1,1,1-trifluoro-4-aryl-3-buten-2-one with a phenylhydrazine, followed by
a treatment with chlorosulphonic acid, or by reacting with chlorosulphonic acid
followed by a reaction with sodium hydroxide and, finally, with thionyl chloride.
The product obtained by either of these methods is made to react with ammonium
carbonate or ammonia, or with sodium sulphite and methyl iodide or methyl sulphate.
In addition, to obtain the enantiomerically pure compounds with the general formula
1 by resolving the racemic mixture with the general formula ()-1, a reaction
is effected with optically active ephedrine, followed by formation of the sodium
salt of each enantiomer, reaction with thionyl chloride and ammonium carbonate
or ammonia, or instead with thionyl chloride followed by sodium sulphite and methyl
iodide or methyl sulphate to thereby obtain separately the enantiomerically pure
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