US 6,310,206 B1Granted

Method for the production of N-(5-amino-2-cyano-4-fluoro-phenyl)-sulphonamides and new intermediate products

AssigneeBayer Aktiengesellschaft

InventorsAchim Hupperts, Mark Wilhelm Drewes, David Erdman, Reinhard Lantzsch

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Abstract

The invention relates to a process for preparing N-(5-amino-2-cyano-4-fluoro-phenyl)-sulphonamides in which, in a first step, 2-amino-4,5-difluoro-benzonitrile is reacted with sulphonyl halides in the presence of an acid acceptor and in the presence of a diluent at temperatures between 0° C. and 150° C. and, in a second step, the N-(2-cyano-4,5-difluoro-phenyl)-sulphon-amides and/or N-(2-cyano-4,5-difluoro-phenyl)-sulphonamides obtained in the first step are as pure substances or as mixtures with ammonia in the presence of a diluent reacted at a temperature between 100° C. and 200° C. The invention furthermore relates to novel intermediates of the process.

Claims17

Dependent claims

A process for preparing a N-(5-amino-2-cyano-4-fluoro-phenyl)-sulphonamide of the formula (I)

wherein
R represents in each case unsubstituted or substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heterocyclyl or heterocyclylalkyl,
comprising the steps of:
a) reacting a 2-amino-4,5-difluoro-benzonitrile of the formula (II)
with a sulphonyl halide of the formula (III)
X—SO2—R (III)
wherein
R is as defined above and
X represents halogen
in the presence of an acid acceptor and in the presence of a diluent at a temperature between 0° C. and 150° C.;
and
b) reacting a N-(2-cyano-4,5-difluoro-phenyl)sulphonamide of the formula (IV) obtained in step a)
wherein
R is as defined above with ammonia in the presence of a diluent at a temperature between 100° C. and 200° C.

11 more elements

Dependencies are inferred from the claim text.

Facts

Application: 09/463,115Filed 18 Jan 2000
Priority: DE 197 31 78324 Jul 1997
Granted: 30 Oct 2001
Term ends: Not estimatedThe source records don’t support an estimate.

Classification6 codes

C07C 311/08
Of an acyclic saturated carbon skeleton: having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a…
C07C 255/58
Having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton: containing cyano groups and singly-bound nitrogen…
C07C 303/38
Of amides of sulfonic acids: by reaction of ammonia or amines with sulfonic acids, or with esters, anhydrides, or halides thereof
C07C 303/40
Of amides of sulfonic acids: by reactions not involving the formation of sulfonamide groups