Patent EP-0165537-B1 (EP)
IPC: C07D413/12
Filed: 1985-06-10
Granted: 1990-01-17
Abstract: 1. Process for the preparation of heteroaryloxyacetamides of the general formula (I)   see diagramm : EP0165537,P17,F2   in which R represents a 5-membered aromatic heterocycle optionally substituted by one or more identical or different substituents, which can also be benzo-fused and which can contain, as heteroatoms, 1 to 3 nitrogen atoms and in addition an oxygen atom or a sulphur atom, the following being suitable substituents : halogen, cyano, nitro, straight-chain or branched alkyl, alkoxy or alkylthio each having up to 4 carbon atoms, straight-chain or branched halogeno-alkyl having up to 4 carbon atoms and up to 9 identical or different halogen atoms, aralkyl, aralkoxy or aralkylthio each having 6 or 10 carbon atoms in the aryl moiety and 1 to 2 carbon atoms in the alkyl moiety, as well as aryl having 6 or 10 carbon atoms, which is optionally substituted by one to three identical or different substituents chosen from C1-4 -alkyl, C1-4 -alkoxy, halogen or C1-4 -halogenoalkyl, and R**1 and R**2 independently of one another represent hydrogen, straight-chain or branched alkyl having 1 to 8 carbon atoms, straight-chain or branched alkenyl and alkynyl each having 2 to 8 carbon atoms, cycloalkyl or cycloalkenyl each having 3 to 7 carbon atoms, which are optionally substituted by one or more identical or different substituents (suitable substituents being, in particular, alkyl radicals having 1 to 4 carbon atoms), straight-chain or branched alkoxy and alkoxyalkyl having 1 to 8 carbon atoms, halogenoalkyl having 1 to 8 carbon atoms and 1 to 5 halogen atoms (in particular fluorine, chlorine and bromine), aralkyl having 6 to 10 carbon atoms in the aryl moiety and 1 to 2 carbon atoms in the alkyl moiety, as well as aryl having 6 or 10 carbon atoms, which is optionally substituted by one or more identical or different substituents, the following being suitable substituents : halogen, straight-chain or branched alkyl, alkoxy or alkylthio each having 1 to 4 carbon atoms, halogenoalkyl, halogenoalkoxy and halogenoalkylthio each having 1 to 2 carbon atoms and 1 to 5 halogen atoms, in particular fluorine, chlorine or bromine, as well as nitro, or R**1 and R**2 , together with the nitrogen atom to which they are bonded, represent a saturated or unsaturated, 5-membered to 7-membered heterocycle optionally substituted by one or more identical or different substituents, which can contain up to 2 further heteroatoms, in particular nitrogen or oxygen, the following being suitable substituents : straight-chain or branched alkyl having 1 to 6 carbon atoms, also in the form of a fused ring system, aryl having 6 or 10 carbon atoms, also in the form of a fused ring system, or dioxyalkylene having 2 to 3 carbon atoms, characterized in that sulphonylated 5-membered heteroaromatics of the general formula (II) R-SO2 -R' in which R has the meaning given above and R' represents lower alkyl or optionally substituted benzyl, are reacted with alpha-oxyacetamides of the general formula (III)   see diagramm : EP0165537,P18,F1   in which R" represents hydrogen or acyl and R**1 and R**2 have the meanings given above, in the presence of an inorganic base as an acid acceptor and of an organic or inorganic solvent as a diluent, if appropriate in the presence of a phase transfer catalyst, at temperatures of -50 degrees C to +150 degrees C.