Ciba-geigy Corporation

Rudolf W Pfluger

Franz Felix

Jean Indermuhle

3-Phenylpyrrole derivatives of formula I ##STR1## wherein X is cyano, --CO--R.sub.3, --CO--OR.sub.3 or ##STR2## R.sub.1 and R.sub.2 are each independently of the other hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 alkylthio, nitro, cyano, halogen or C.sub.1 -C.sub.6 haloalkyl, or R.sub.1 and R.sub.2, when taken together, are methylenedioxy or difluoromethylenedioxy, R.sub.3 is C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, phenyl or benzyl, or phenyl or benzyl which are each substituted by halogen, methyl, methoxy or methylthio, and R.sub.4 is hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, phenyl or benzyl, or phenyl or benzyl which are each substituted by halogen, methyl, methoxy or methylthio, are prepared by (a) reacting N-(p-tolylsulfonyl)methyl formamide, in an inert solvent and in the presence of an organic base, with phosphoroxy chloride, mixing the reaction solution with water, separating the aqueous phase of the resultant two-phase mixture, and (b) reacting the organic phase containing (p-tolylsulfonyl)methyl isocyanide direct with a compound of formula II ##STR3## wherein X, R.sub.1 and R.sub.2 are as defined for formula I, Y is --CO--NHR.sub.4, --CO--R.sub.5 or --S--R.sub.5, R.sub.5 is C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, phenyl or benzyl, or phenyl or benzyl which are each substituted by halogen, methyl, methoxy or methylthio, and R.sub.4 is as defined for formula I, in the presence of a base.

Process for the preparation of 3-phenylpyrrole derivatives

A novel process for producing fluoroalkoxyaminopyrimidines of the formula I ##STR1## wherein R is hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy or benzyl, X is halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylamino or di-C.sub.1 -C.sub.4 -alkylamino, and T is hydrogen, chlorofluoromethyl, bromofluoromethyl, difluoromethyl or 1,2,2,2-tetrafluoroethyl, characterized in that a thiopyrimidine of the formula II ##STR2## wherein Y has the meaning given for X under the formula I or is hydroxyl, A is hydrogen, sodium, potassium or an equivalent of calcium or magnesium, and Q is C.sub.1 -C.sub.4 -alkyl, phenyl or benzyl, is reacted with difluorochloromethane, difluorobromomethane, tetrafluoroethylene, perfluoropropylene, trifluorobromoethylene or trifluorochloroethylene in the presence of a base; the resulting compound of the formula III ##STR3## is converted by oxidation into a compound of the formula IV ##STR4## wherein n is the number one or two; and this compound is treated with an amine of the formula V

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Zeiningen, Switzerland

Rudolf W Pfluger