Patent ID: 6207830
Filing Date: 2001-03-27
Classification: C07D

Abstract:
In a process for the production of compounds of the formula I ##STR73##whereinR.sub.1 is methyl or ethyl;R.sub.2 is --CF.sub.3, --CClF.sub.2, --CCl.sub.2 F or --C.sub.2 F.sub.5 ; andQ is a group ##STR74## ##STR75##X and Y, independently of one another, are oxygen or sulphur;R.sub.3 signifies hydrogen, fluorine or chlorine;R.sub.4 signifies hydrogen, fluorine, chlorine, bromine, cyano, nitro, methyl or difluoromethyl;R.sub.5 signifies hydrogen, halogen, cyano, nitro, hydroxy, C.sub.1-6 -alkoxy, C.sub.1-6 -alkylthio, C.sub.2-6 -alkenyloxy, C.sub.2-6 -alkinyloxy, C.sub.1-6 -halogenalkoxy, C.sub.2-6 halogen-alkenyloxy, C.sub.2-8 -alkylcarbonyl-alkoxy, C.sub.2-8 -alkoxycarbonylalkoxy, C.sub.1-3 -alkyl-oxiranylmethoxy, ##STR76##C.sub.4-8 -alkenyloxycarbonylalkoxy or C.sub.4-8 -alkinyloxycarbonylalkoxy;R.sub.20 is hydrogen or C.sub.1-4 -alkyl;R.sub.21 and R.sub.22, independently of one another, signify C.sub.1-4 -alkyl; or R.sub.21 and R.sub.22 together signify a C.sub.23 -alkylene bridge;R.sub.23 signifies cyano or COR.sub.6 ;R.sub.24 signifies hydrogen or halogen;R.sub.6 signifies OH, C.sub.1-6 -alkoxy, C.sub.2-6 -alkenyloxy, C.sub.2-6 -alkinyloxy, C.sub.2-8 -alkoxyalkoxy, C.sub.3-6 -cycloalkoxy, C.sub.3-6 -cycloalkenyloxy, C.sub.3-6 -cycloalkyl-C.sub.1-6 -alkoxy, C.sub.1-6 -halogen-alkoxy, C.sub.2-6 -halogen-alkenyloxy, C.sub.1-6 -hydroxycarbonylalkoxy, C.sub.3-8 -alkoxycarbonylalkoxy, C.sub.3-8 -alkenyloxycarbonylalkoxy, C.sub.3-8 -alkinyloxycarbonylalkoxy, N(C.sub.1-3 -alkyl).sub.2 or N(C.sub.3-4 -alkenyl).sub.2 ;R.sub.7 signifies C.sub.1-6 -alkyl, C.sub.2-6 -alkenyl, C.sub.2-6 -alkiny], C.sub.2-8 -alkoxyalkyl, C.sub.3-6 -cycloalkyl, C.sub.1-6 -halogenalkyl, C.sub.2-6 -halogen-alkenyl, C.sub.2-6 -alkylsulfonyloxyalkyl, C.sub.1-10 -phenylsulfonyloxyalkyl, N(C.sub.1-5 -alkyl).sub.2 or diallylamino;R.sub.8 signifies hydrogen, C.sub.1-6 -alkyl, C.sub.2-6 -alkenyl, C.sub.2-6 -alkinyl, C.sub.2 -C.sub.10 -alkoxyalkyl, C.sub.3-6 -cycloalkyl, C.sub.3-6 -cycloalkenyl, C.sub.1-6 -halogen-alkyl, C.sub.3-6 -halogen-alkenyl, C.sub.2-6 -hydroxycarbonylalkyl, C.sub.3-8 -alkoxycarbonylalkyl, C.sub.3-8 -alkenyloxycarbonytalkyl or C.sub.3-8 -alkinyloxycarbonylalkyl;R.sub.9 signifies hydrogen, OH, CH.sub.2 COOR.sub.15, CH.sub.2 CON(C.sub.1-4 -alkyl).sub.2, CH.sub.2 CON(C.sub.3-4 -alkenyl).sub.2, COOR.sub.16, CON(C.sub.1-4 -alkyl).sub.2, CON(C.sub.3-4 -alkenyl).sub.2, C.sub.1-6 -alkyl, hydroxy-C.sub.1-6 -alkyl, C.sub.2-10 -alkoxycarbonyl-alkoxy or C.sub.2,.sub.8 -alkoxyalkyl;R.sub.10 signifies hydrogen, Cyano, C .sub.1-6 -alkyl, C.sub.2-6 -alkenyl, C.sub.2-6 -alkinyl, hydroxy-C.sub.1-6 -alkyl, C.sub.2-8 -alkoxyalkyl, C.sub.3-6 -cycloalkyl, C.sub.1-6 -halogen-alkyl, COOR.sub.17, CON(C.sub.1-4 -alkyl).sub.2 or CON(C.sub.3-4 -alkenyl).sub.2 ;R.sub.11 signifies hydrogen, C.sub.1-6 -alkyl or C.sub.1-6 -halogen-alkyl;R.sub.12 signifies hydrogen, C.sub.1-6 -alkyl, C.sub.1-6 -halogen-alkyl, CH.sub.2 OH, C.sub.2-6 -alkoxyalkyl, C.sub.2-6 -halogenalkoxyalkyl, COOR.sub.18, CON(C.sub.1-4 -alkyl).sub.2 or CON(C.sub.3-4 -alkenyl).sub.2 ;R.sub.13 signifies hydrogen, C.sub.3-16 -trialkylsilyloxy, C.sub.1-6 -alkoxy, chlorine, C.sub.1-6 -alkyl, C.sub.2-6 -alkenyl, C.sub.2-6 -alkinyl, C.sub.3-6 -cycloalkyl, C.sub.3-6 -cycloalkenyl, C.sub.1-6 -halogen-alkyl, C.sub.2-6 -halogen-alkenyl or C.sub.1-6 -hydroxycarbonylalkyl;R.sub.14 signifies hydrogen, C.sub.1-6 -alkyl or C.sub.1-6 -halogenalkyl;R.sub.15 signifies hydrogen, C.sub.1-6 -alkyl, C.sub.2-6 -alkenyl, C.sub.2-6 -alkinyl, C.sub.2-8 -alkoxyalkyl, C.sub.3-6 -cycloalkyl, C.sub.3-6 -cycloalkenyl, C.sub.1-6 -halogen-alkyl, C.sub.2-6 -halogen-alkenyl, C.sub.2-6 -hydroxycarbonylalkyl, C.sub.3-8 -alkoxycarbonylalkyl, C.sub.3-8 -alkenyloxycarbonylalkyl or C.sub.3-8 -alkinyloxycarbonylalkyl;R.sub.16 signifies hydrogen, C.sub.1-6 -alkyl, C.sub.2-6 -alkenyl, C.sub.2-6 -alkinyl, C.sub.2-8 -alkoxyalkyl, C.sub.3-6 -cycloalkyl, C.sub.3-6 -cycloalkenyl, C.sub.1-6 -halogen-alkyl, C.sub.2-6 -halogen-alkenyl, C.sub.2-6 -hydroxycarbonylalkyl, C.sub.3-8 -alkoxycarbonylalkyl, C.sub.3-8 -alkenyloxycarbonylalkyl or C.sub.3-8 -alkinyloxycarbonylalkyl;R.sub.17 signifies hydrogen, C.sub.1-6 -alkyl, C.sub.2-6 -alkenyl, C.sub.2-6 -alkinyl, C.sub.2-8 -alkoxyalkyl, C.sub.3-6 -cycloalkyl, C.sub.3-6 -cycloalkenyl, C.sub.1-6 -halogen-alkyl, C.sub.2-6 -halogen-alkenyl, C.sub.2-6 -hydroxycarbonylalkyl, C.sub.2-8 -alkoxycarbonylalkyl, C.sub.3-8 -alkenyloxycarbonylalkyl or C.sub.3-8 -alkinyloxycarbonylalkyl; andR.sub.18 signifies hydrogen, C.sub.1-6 -alkyl, C.sub.2-6 -alkenyl, C.sub.2-6 -alkinyl, C.sub.2-8 -alkoxyalkyl, C.sub.3-6 -cycloalkyl, C.sub.3-6 -cycloalkenyl, C.sub.1-6 -halogen-alkyl, C.sub.2-6 -halogen-alkenyl, C.sub.2-6 -hydroxycarbonylalkyl, C.sub.3-8 -alkoxycarbonylalkyl, C.sub.3-8 -alkenyloxycarbonylalkyl or C.sub.3-8 -alkinyloxycarbonylalkyl;by reacting an isocyanate of the formula IIO.dbd.C.dbd.N--Q (II)wherein Q has the meaning given under formula I, with an enamine of the formula III, at a temperature -5.degree. C. to +50.degree. C. ##STR77##wherein R.sub.1 and R.sub.2 have the meanings given under formula I in the presence of a base and in the presence of an inert solvent;the improvement which comprises carrying out the reaction of the isocyanate of the formula II with the enamine of the formula III in the presence of 0.1 to 0.3 equivalents of a base selected from potassium tert.butylate, sodium tert.butylate, sodium methylate, sodium ethylate, potassium methylate, potassium ethylate, sodium hydride, potassium hydride, sodium pentylate, potassium pentylate and 1,8-diazabicyclo[5.4.0]undec-7-ylene (DBU).