Patent ID: 8680283

Claim:
Process for the preparation of 5-substituted 1-alkyltetrazolyl oxime derivatives of the general formula (I) in which R 1 is alkyl, or phenyl optionally monosubstituted by halogen, cyano, nitro, C 1 -C 8 -alkyl, C 1 -C 8 -alkoxy, methylsulphonyl, trifluoromethyl or aryl, R 2 is C 1 -C 12 -alkyl, C 1 -C 12 -haloalkyl or an alkoxyalkyl of the formula -[A-O] m —B, A is C 2 -C 4 -alkanediyl (alkylene), B is C 1 -C 6 -alkyl, m is 1 or 2, R 3 is a pyridinyl group (Het 1 ) or a thiazolyl group (Het 2 ) in which R is hydrogen or halogen, Z is hydrogen, halogen, in each case substituted or unsubstituted C 1 -C 8 -alkyl, C 3 -C 8 -cycloalkyl, C 2 -C 8 -alkenyl, C 2 -C 8 -alkynyl, or the group—N(R a )C(═O)Q, Q is hydrogen, in each case substituted or unsubstituted C 1 -C 8 -alkyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkenyl-C 1 -C 8 -alkyl, C 3 -C 8 -halocycloalkyl having 1 to 5 halogen atoms, C 3 -C 8 -cycloalkyl-C 1 -C 8 -alkyl, C 3 -C 8 -cycloalkenyl, C 2 -C 8 -alkenyl, C 2 -C 8 -haloalkenyl having 1 to 5 halogen atoms, C 2 -C 8 -alkynyl, C 2 -C 8 -haloalkynyl having 1 to 5 halogen atoms, C 1 -C 8 -alkoxy, C 1 -C 8 -haloalkoxy having 1 to 5 halogen atoms, C 1 -C 8 -haloalkoxyalkyl having 1 to 5 halogen atoms, C 2 -C 8 -alkenyloxy, C 2 -C 8 -haloalkenyloxy having 1 to 5 halogen atoms C 3 -C 8 -alkynyloxy, C 3 -C 8 -haloalkynyloxy having 1 to 5 halogen atoms, C 1 -C 8 -alkylamino, (C 1 -C 6 -alkoxyimino)-C 1 -C 6 -alkyl, (C 1 -C 6 -alkenyloxyimino)-C 1 -C 6 -alkyl, (C 1 -C 6 -alkinyloxyimino)-C 1 -C 6 -alkyl, (benzyloxyimino)-C 1 -C 6 -alkyl, C 1 -C 8 -alkylsulphenyl, arylsulphenyl, tri(C 1 -C 8 -alkyl)silyl-C 1 -C 8 -alkyl, tri(C 1 -C 8 -alkyl)silyloxy, tri(C 1 -C 8 alkyl)silyl-C 3 -C 8 -cycloalkyl, aryl, phenoxy, phenoxyalkyl, benzyloxy, heterocyclyl, C 5 -C 12 -bicycloalkyl, C 5 -C 12 -bicycloalkenyl, benzo-fused C 5 -C 12 -carbocyclyl, R a is hydrogen, in each case substituted or unsubstituted C 1 -C 8 -alkyl, C 3 -C 8 -cycloalkyl, C 2 -C 8 -alkenyl, C 2 -C 8 -alkynyl, aryl, heterocyclyl, wherein the compounds of formula (I) may be present in pure form or else as mixtures of different possible isomeric forms; characterized in that (1) in a first step, oximes of the general formula (II) in which R 1 and R 2 have the meanings given above, are reacted with compounds of the general formula (III) in which R 3 has the meanings given above and Y is chlorine, bromine, iodine, mesylate or tosylate, and the oxime ethers of the general formula (IV) obtained in this way in which R 1 , R 2 and R 3 have the meanings given above, (2) are reacted in a second step with perfluoroalkylsulphonic acid esters (R 4 —SO 2 —Oalkyl) or anhydrides [(R 4 -SO 2 ) 2 O], and the compounds of the general formula (V) obtained in this way in which R 1 , R 2 and R 3 have the meanings given above and R 4 is perfluoroalkyl, (3) are reacted in a third step with azides of the formula R 5 —N 3 wherein R 5 is selected from the group consisting of sodium, potassium, tetrabutylammonium, trimethylsilyl and disphenylphosphoryl.