Ciba-Geigy Corporation

Syngenta Crop Protection, Inc.

Novartis Corporation

Novartis Crop Protection, Inc.

Reinhard Georg Hanreich

Felix Spindler

Hans-Peter Jalett

Hans-Ulrich Blaser

Willy Baettig

A process for the hydrogenation of imines with hydrogen under elevated pressure in the presence of iridium catalysts and with or without an inert solvent, wherein the reaction mixture contains an ammonium or metal chloride, bromide or iodide and additionally an acid.

Process for the hydrogenation of imines

Unlike (4-cyclopropyl-6-methyl-pyrimidin-2-yl)-phenyl-amine of the known crystal modification A, (4-cyclopropyl-6-methyl-pyrimidin-2-yl)-phenyl-amine of crystal modification B of high eutectic purity (content at least 98%) and having a melting point of from 73.degree. C. to 75.degree. C., as a fungicidal active ingredient in plant-protection compositions, does not have a tendency to crystal growth. Such compositions have a high degree of storage stability and retain their original good suspensibility and dispersibility.

Crystal modification of

In accordance with a novel process, 2-(2-chloroethoxy)-benzenesulfonamide of formula I ##STR1## is prepared by etherification of 4-chlorophenol of formula II ##STR2## with ethylene carbonate and chlorination of the resulting 4-(2-hydroxyethoxy)-chlorobenzene of formula III ##STR3## with phosgene or thionyl chloride to give 4-(2-chloroethoxy)-chlorobenzene of formula IV ##STR4## which is converted with chlorosulfonic acid ClSO.sub.3 H and sodium hydroxide to the sulfonic acid sodium salt of formula V ##STR5## which is hydrogenated to the compound of formula VI ##STR6## which is subsequently reacted with phosgene to the sulfonic acid chloride of formula VII ##STR7## which is reacted with amonia to the sulfonamide of formula I.

Process for the preparation of 2-(2-chloroethoxy)-benzenesulfonamide

Growing community of inventors

Basle, Switzerland

Reinhard Georg Hanreich