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1. WO1999005098 - METHOD FOR THE PRODUCTION OF N-(5-AMINO-2-CYANO-4-FLUORO-PHENYL)-SULPHONAMIDES AND NEW INTERMEDIATE PRODUCTS

Publication Number WO/1999/005098
Publication Date 04.02.1999
International Application No. PCT/EP1998/004324
International Filing Date 13.07.1998
Chapter 2 Demand Filed 04.12.1998
IPC
C07C 255/58 2006.1
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
CACYCLIC OR CARBOCYCLIC COMPOUNDS
255Carboxylic acid nitriles
49having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
58containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton
C07C 303/38 2006.1
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
CACYCLIC OR CARBOCYCLIC COMPOUNDS
303Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
36of amides of sulfonic acids
38by reaction of ammonia or amines with sulfonic acids, or with esters, anhydrides, or halides thereof
C07C 303/40 2006.1
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
CACYCLIC OR CARBOCYCLIC COMPOUNDS
303Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
36of amides of sulfonic acids
40by reactions not involving the formation of sulfonamide groups
C07C 311/08 2006.1
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
CACYCLIC OR CARBOCYCLIC COMPOUNDS
311Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
01Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
02of an acyclic saturated carbon skeleton
08having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
C07C 311/48 2006.1
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
CACYCLIC OR CARBOCYCLIC COMPOUNDS
311Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
48having nitrogen atoms of sulfonamide groups further bound to another hetero atom
CPC
C07C 255/58
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
CACYCLIC OR CARBOCYCLIC COMPOUNDS
255Carboxylic acid nitriles
49having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
58containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton
C07C 303/38
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
CACYCLIC OR CARBOCYCLIC COMPOUNDS
303Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
36of amides of sulfonic acids
38by reaction of ammonia or amines with sulfonic acids, or with esters, anhydrides, or halides thereof
C07C 303/40
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
CACYCLIC OR CARBOCYCLIC COMPOUNDS
303Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
36of amides of sulfonic acids
40by reactions not involving the formation of sulfonamide groups
C07C 311/08
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
CACYCLIC OR CARBOCYCLIC COMPOUNDS
311Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
01Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
02of an acyclic saturated carbon skeleton
08having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
C07C 311/48
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
CACYCLIC OR CARBOCYCLIC COMPOUNDS
311Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
48having nitrogen atoms of sulfonamide groups further bound to another hetero atom
Applicants
  • BAYER AKTIENGESELLSCHAFT [DE]/[DE] (AllExceptUS)
  • HUPPERTS, Achim [DE]/[DE] (UsOnly)
  • DREWES, Mark, Wilhelm [DE]/[DE] (UsOnly)
  • ERDMAN, David [US]/[DE] (UsOnly)
  • LANTZSCH, Reinhard [DE]/[DE] (UsOnly)
Inventors
  • HUPPERTS, Achim
  • DREWES, Mark, Wilhelm
  • ERDMAN, David
  • LANTZSCH, Reinhard
Common Representative
  • BAYER AKTIENGESELLSCHAFT
Priority Data
197 31 783.924.07.1997DE
Publication Language German (de)
Filing Language German (DE)
Designated States
Title
(DE) VERFAHREN ZUR HERSTELLUNG VON N-(5-AMINO-2-CYANO-4-FLUOR-PHENYL)-SULFONAMIDEN UND NEUE ZWISCHENPRODUKTE
(EN) METHOD FOR THE PRODUCTION OF N-(5-AMINO-2-CYANO-4-FLUORO-PHENYL)-SULPHONAMIDES AND NEW INTERMEDIATE PRODUCTS
(FR) PROCEDE DE PRODUCTION DE N-(5-AMINO-2-CYANO-4-FLUOROPHENYL)-SULFONAMIDES ET NOUVEAUX PRODUITS INTERMEDIAIRES
Abstract
(DE) Die Erfindung betrifft ein Verfahren zum Herstellen von N-(5-Amino-2-cyano-4-fluor-phenyl)-sulfonamiden, worin in einem ersten Schritt 2-Amino-4,5-difluor-benzonitril mit Sulfonsäurehalogeniden in Gegenwart eines Säureakzeptors und in Gegewart eines Verdünnungsmittels bei Temperaturen zwischen 0 °C und 150 °C umgesetzt wird und worin in einem zweiten Schritt die im ersten Schritt erhaltenen N-(2-Cyano-4,5-difluor-phenyl)-sulfonamide und/oder N-(2-Cyano-4,5-difluor-phenyl)-sulfonimide als reine Stoffe oder als Gemische mit Ammoniak in Gegenwart eines Verdünnungsmittels bei Temperatur zwischen 100 °C und 200 °C umgesetzt werden. Die Erfindung betrifft weiterhin neue Zwischenprodukte des Verfahrens.
(EN) The invention relates to a method for producing N-(5-amino-2-cyano-4-fluoro-phenyl)-sulphonamides. In a first step, 2-amino-4,5-difluoro-benzonitrile is reacted with sulphonic acid halogenides in the presence of an acid acceptor and a diluting agent at temperatures between 0 °C and 150 °C. In a second step, the N-(2-cyano-4,5-difluoro-phenyl)-sulphonamide and/or N-(2-cyano-4,5-difluoro-phenyl)-sulphonamides are reacted, either in the pure state or mixed, with ammonia in the presence of a diluting agent at temperatures between 100 °C and 200 °C. The invention also relates to new intermediate products of this method.
(FR) L'invention concerne un procédé de production de N-(5-amino-2-cyano-4-fluorophényl)-sulfonamides. Dans une première étape, on fait réagir du 2-amino-4,5-difluorobenzonitrile avec des halogénures d'acide sulfonique, en présence d'un accepteur d'acide et en présence d'un agent de dilution, à des températures comprises entre 0 °C et 150 °C. Dans une deuxième étape, on fait réagir les N-(2-cyano-4,5-difluorophényl)-sulfonamides ou N-(2-cyano-4,5-difluorophényl)-sulfonimides obtenus à l'étape 1, purs ou mélangés, avec de l'ammoniac, en présence d'un agent de dilution, à des températures comprises entre 100 °C et 200 °C. L'invention concerne en outre de nouveaux produits intermédiaires du procédé.
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