Patent ID: 7737275

Claim:
A process for preparing a compound of formula I where the variables are each defined as follows: R 1 is hydrogen, cyano, amino, C 1 -C 6 -alkyl, C 1 -C 3 -cyanoalkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -haloalkoxy, C 3 -C 7 -cycloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 3 -C 6 -alkynyl, C 3 -C 6 -haloalkynyl or phenyl-C 1 -C 4 -alkyl; R 2 and R 3 are each independently hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 7 -cycloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 3 -C 6 -alkynyl or C 3 -C 6 -haloalkynyl; X 1 , X 2 and X 3 are each independently oxygen or sulfur; Ar is phenyl, which may be mono- or polysubstituted by the following groups: hydrogen, halogen, cyano, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl; and A is —NR 5 R 6 where the variables R 5 and R 6 are each independently hydrogen, C 1 -C 10 -alkyl, C 2 -C 10 -alkenyl or C 2 -C 10 -alkynyl, each of which may be unsubstituted or substituted by one of the following radicals: C 1 -C 4 -alkoxy, C 1 -C 4 -alkylthio, CN, NO 2 , formyl, C 1 -C 4 -alkylcarbonyl, C 1 -C 4 -alkoxycarbonyl, C 1 -C 4 -alkylaminocarbonyl, C 1 -C 4 -dialkylaminocarbonyl, C 1 -C 4 -alkylsulfinyl, C 1 -C 4 -alkylsulfonyl, C 3 -C 10 -cycloalkyl, 3- to 8-membered heterocyclyl having from one to three heteroatoms selected from O, S, N and an NR 7 group where R 7 is hydrogen, C 1 -C 6 -alkyl, C 3 -C 6 -alkenyl or C 3 -C 6 -alkynyl; or C 1 -C 10 -haloalkyl, C 2 -C 10 -haloalkenyl or C 2 -C 10 -haloalkynyl; comprising reacting a phenyl iso(thio)cyanate of the formula II where the variables X 1 , X 3 , Ar and A are each as defined above, with an enamine of the general formula III where R 1a is as defined above for R 1 with the exception of amino; R 2 , R 3 and X 2 are each as defined above; and R 4 is C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 3 -alkoxy-C 1 -C 3 -alkyl, C 1 -C 3 -alkylthio-C 1 -C 3 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 3 -C 6 -alkynyl, C 3 -C 6 -haloalkynyl, C 3 -C 7 -cycloalkyl, C 1 -C 6 -cyanoalkyl or benzyl which is itself unsubstituted or substituted on the phenyl ring by methyl, methoxy, methylthio, halogen, nitro or cyano; in the presence of from 1.8 to 2.6 base equivalents per mole of the phenyl iso(thio)cyanate of the formula II; and, if appropriate, in a further step, reacting the resulting 3-phenyl(thio)uracil or 3-phenyldithiouracil of the formula I where R 1 =R 1a , where R 1 is hydrogen, with an aminating agent of the formula IV H 2 N-L 1 IV where L 1 is a nucleophilic leaving group to give a 3-phenyl(thio)uracil or 3-phenyldithiouracil of the formula I where R 1 =amino.