Ciba-geigy Corporation

Klaus-Jurgen Coers

Alfred Grieder

Peter Labuhn

A process is described for the preparation of N-(1'-alkoxycarbonylethyl)-2,6-dialkylanilines of the formula ##STR1## in which R.sub.1 and R.sub.2 are each methyl or ethyl and R.sub.3 is an alkyl group having 1 to 4 carbon atoms, this process being based on the reaction of a corresponding 2,6-dialkylaniline with a corresponding alkyl 2-chloropropionate or alkyl 2-bromopropionate. The process is carried out by carrying out the reaction of the 2,6-dialkylaniline with the 2-halogenopropionic acid ester at 110.degree.-130.degree. C. in the presence of an alkali metal iodide as the catalyst, and of an alkali metal carbonate or alkali metal bicarbonate as an acid acceptor, in excess 2,6-dialkylaniline as the solvent, removing, by distillation, the water formed during the reaction and working up the organic phase, which is obtained after adding water and separating the phases, by distillation. The N-(1'-alkoxycarbonylethyl)-2,6-dialkylanilines of the above formula which can be prepared by this process are valuable intermediates for the preparation of compounds having a pesticidal action.

Process for the preparation of

A process is described for the preparation of N-(1'-alkoxycarbonylethyl)-2,6-dialkylanilines of the formula ##STR1## in which R.sub.1 and R.sub.2 are each methyl or ethyl and R.sub.3 is an alkyl group having 1 to 4 carbon atoms, this process being based on the reaction of a corresponding 2,6-dialkylaniline with a corresponding alkyl 2-bromopropionate. The process is carried out by carrying out the reaction of the 2,6-dialkylaniline with the alkyl 2-bromopropionate at 110.degree. to 125.degree. C. in excess 2,6-dialkylaniline as the solvent, in the presence of a quaternary compound of nitrogen or of phosphorus, and in the presence of an alkali metal carbonate or alkali metal bicarbonate as an acid acceptor, distilling off the water formed during the reaction and working up the organic phase, which is obtained after adding water and separating the phases, by distillation. The N-(1'-alkoxycarbonylethyl)-2,6-dialkylanilines of the above formula which can be prepared by this process are valuable intermediates for the preparation of compounds having a pesticidal action.

A process is described for the preparation of N-(1'-alkoxycarbonylethyl)-2,6-dialkylanilines of the formula ##STR1## in which R.sub.1 and R.sub.2 are each methyl or ethyl and R.sub.3 is an alkyl group having 1-4 carbon atoms. According to this process, a 2-chloropropionic acid ester having 1-4 carbon atoms in the alkyl group is reacted in the presence of water and of a quaternary ammonium or phosphonium salt with an alkali metal iodide to give a mixture of the 2-chloropropionic acid ester and the 2-iodopropionic acid ester, and this mixture is subsequently reacted, after separating off the aqueous phase, at 110-130.degree. C., in the presence of an alkali metal carbonate or alkali metal bicarbonate as an acid-binding agent, with excess 2,6-dialkylaniline, the reaction mixture is extracted with water and the mixture of the 2,6-dialkylaniline of the formula IV and the N-(1'-alkoxycarbonylethyl)-2,6-dialkylaniline of the formula I, which is obtained after separating off the aqueous extract, is separated by distillation. The N-(1'-alkoxycarbonylethyl)-2,6-dialkylanilines of the above formula which can be prepared by this process are valuable intermediates for the preparation of compounds having a pesticidal action.

Growing community of inventors

Reinach, Switzerland

Klaus-Jurgen Coers