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1. WO2004002969 - METHOD FOR PRODUCING 3,4-DICHLORO-N-(2-CYANO-PHENYL)-5-ISOTHIAZOLE CARBOXAMIDE

Publication Number WO/2004/002969
Publication Date 08.01.2004
International Application No. PCT/EP2003/006361
International Filing Date 17.06.2003
Chapter 2 Demand Filed 18.10.2003
IPC
C07D 275/03 2006.01
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
DHETEROCYCLIC COMPOUNDS
275Heterocyclic compounds containing 1, 2-thiazole or hydrogenated 1,2-thiazole rings
02not condensed with other rings
03with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
CPC
C07D 275/03
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
DHETEROCYCLIC COMPOUNDS
275Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
02not condensed with other rings
03with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
Applicants
  • BAYER CROPSCIENCE AKTIENGESELLSCHAFT [DE]/[DE] (AllExceptUS)
  • HIMMLER, Thomas [DE]/[DE] (UsOnly)
Inventors
  • HIMMLER, Thomas
Common Representative
  • BAYER CROPSCIENCE AKTIENGESELLSCHAFT
Priority Data
102 28 731.727.06.2002DE
Publication Language German (DE)
Filing Language German (DE)
Designated States
Title
(DE) VERFAHREN ZUR HERSTELLUNG VON 3,4-DICHLOR-N-(2-CYANO-PHENYL)-5-ISOTHIAZOL-CARBOXAMID
(EN) METHOD FOR PRODUCING 3,4-DICHLORO-N-(2-CYANO-PHENYL)-5-ISOTHIAZOLE CARBOXAMIDE
(FR) PROCEDE DE PRODUCTION DE 3,4-DICHLORO-N-(2-CYANO-PHENYLE)-5-ISOTHIAZOL-CARBOXAMIDE
Abstract
(DE)
Nach einem neuen Eintopf-Verfahren wird 3,4-Dichlor-N-(2-cyano-phenyl)-5-isothiazolcarboxamid dadurch hergestellt, dass man a) Isatosäureanhydrid in Gegenwart von Dimethylformamid mit Ammoniakgas umsetzt, b) dann das dabei entstandene Anthranilsäureamid ohne vorherige Isolierung mit 3,4-Dichlor-isothiazolcarbonsäurechlorid in Gegenwart eines Säureakzeptors und in Gegenwart von Dimethylformamid umsetzt und c) anschliessend das dabei entstandene N-[2-(Aminocarbonyl)-phenyl]-3,4-dichlor-isothiazolcarboxamid ohne vorherige Isolierung in Gegenwart von Dimethylformamid mit Thionylchlorid, Phosphoroxychlorid, Phosgen oder Chlormethylen-dimethylammoniumchlorid umsetzt.
(EN)
The invention relates to a novel one-pot method for producing 3,4-dichloro-N-(2-cyano-phenyl)-5-isothiazole carboxamide. According to said method, a) isatoic acid anhydride is reacted with ammonia gas in the presence of dimethylformamide, b) the anthranilic acid amide thus obtained is reacted with 3,4-dichloro-isothiazole carboxylic acid chloride, without being previously isolated, in the presence of an acid acceptor and in the presence of dimethylformamide, and c) the N-[2-(aminocarbonyl)-phenyl]-3,4-dichloro-isothiazole carboxamide thus obtained is reacted with thionyl chloride, phosphorus oxychloride, phosgene or chloromethylene-dimethylammonium chloride, without being previously isolated, in the presence of dimethylformamide.
(FR)
L'invention concerne un nouveau procédé de production dans un seul pot de 3,4-dichloro-N-(2-cyano-phényle)-5-isothiazolcarboxamide. Ce procédé consiste a) à faire réagir de l'anhydride d'acide isatique en présence de diméthylformamide avec un gaz d'ammoniac puis b) puis à faire réagir l'amide d'acide anthranilique ainsi engendré sans isolation préalable avec du chlorure d'acide 3,4-dichloro-isothiazolcarbonique en présence d'un récepteur d'acide et en présence de diméthylformamide et enfin c) à faire réagir le N-[2-(aminocarbonyle)-phényle]-3,4-dichloro-isothiazolcarboxamide sans isolation préalable en présence de diméthylformamide avec du chlorure de thionyle, de l'oxychlorure de phosphore, du phosgène ou du chlorométhylène-dimélthylammoniumchlorure.
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