WO2004002968A1 - Verfahren zur herstellung von 3,4-dichlor-n-(2-cyano-phenyl)-5-isothiazolcarboxamid - Google Patents
Verfahren zur herstellung von 3,4-dichlor-n-(2-cyano-phenyl)-5-isothiazolcarboxamid Download PDFInfo
- Publication number
- WO2004002968A1 WO2004002968A1 PCT/EP2003/006360 EP0306360W WO2004002968A1 WO 2004002968 A1 WO2004002968 A1 WO 2004002968A1 EP 0306360 W EP0306360 W EP 0306360W WO 2004002968 A1 WO2004002968 A1 WO 2004002968A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- dichloro
- phenyl
- formula
- cyano
- isothiazole
- Prior art date
Links
- WLPCAERCXQSYLQ-UHFFFAOYSA-N N#Cc1ccccc1NC(c([s]nc1Cl)c1Cl)=O Chemical compound N#Cc1ccccc1NC(c([s]nc1Cl)c1Cl)=O WLPCAERCXQSYLQ-UHFFFAOYSA-N 0.000 description 3
- MSSXWKAJMRSAGF-UHFFFAOYSA-N O=C(c([s]nc1Cl)c1Cl)Cl Chemical compound O=C(c([s]nc1Cl)c1Cl)Cl MSSXWKAJMRSAGF-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
- C07D275/02—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings
- C07D275/03—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings with 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
Definitions
- the present invention relates to a new process for the preparation of the known 3,4-dichloro-N- (2-cyano-phenyl) -5-isothiazole carboxamide, which can be used as an active ingredient with microbicidal properties.
- the method according to the invention is characterized by a number of advantages.
- Suitable acid acceptors when carrying out the first stage of the process according to the invention are preferably tertiary amines.
- tertiary amines examples include trimethylamine, triemylarnine, tributylamine, N, N-dimethylbenzylamine, pyridine, N-methylpiperidine, N-methylmorpholine, N, N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclonones (DBN) or diazabicycloundecene (DBU ).
- Halogenated aromatic hydrocarbons such as toluene or chlorobenzene
- chlorinated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, dichloroethane or trichloroethane
- amides such as dimethylformamide and dimethylacetamide. Dimethylformamide is particularly preferred.
- Suitable dehydrating agents for carrying out the second stage of the process according to the invention are all those reagents which are suitable for eliminating water from A iden.
- Mixtures of dimethylformamide and thionyl chloride, phosphorus oxychloride, phosgene or CMormethylene-dimethylammmonium chloride can preferably be used.
- All customary aprotic, organic solvents can be used as diluents when carrying out the second stage of the process according to the invention.
- Halogenated aromatic hydrocarbons such as toluene or chlorobenzene, can preferably be used, furthermore chlorinated hydrocarbons, such as dichloromethane, chloroform, carbon tetrachloride, dichloroethane or
- Trichloroethane and also amides such as dimethylformamide and dimethylacetamide.
- Dimethylformamide is particularly preferred.
- the temperatures can be varied within a substantial range when carrying out the process according to the invention.
- the first stage is carried out at temperatures between 0 ° C. and 160 ° C., preferably between 0 ° C. and 120 ° C.
- work is generally carried out at temperatures between -20 ° C. and + 80 ° C., preferably between 0 ° C. and 60 ° C.
- reaction in the first stage and the second stage is generally carried out under atmospheric pressure. However, it is also possible to work under increased pressure.
- N- [2- (aminocarbonyl) phenyl] -3,4-dichloro-5-isothiazolecarboxamide of the formula (TV) are generally employed of dehydrating agent and optionally an excess of dimethylformamide.
- the preparation Processing takes place according to customary methods, in general the procedure is followed by adding water to the reaction mixture and suctioning off, washing and drying the resulting solids.
- the method according to the invention can be carried out as a one-pot reaction.
- 3,4-dichloroisothiazole-5-carboxylic acid chloride of the formula (LT) is first reacted with anthranilic acid amide of the formula (HI) in the presence of acid acceptor and then added without prior isolation of the N- [2- (ammocarbonyl) phenyl] -3,4-dicMor-isothiazolcarboxamids of formula (TV) add the dehydration reagent.
- the processing is again carried out according to the usual
- a solution of 4.33 g (22 mmol) of 3,4-dichloroisothiazolecarboxylic acid chloride is added to a mixture of 15 ml of dimethylformamide, 3 g (22 mmol) of anthranilic acid amide and 2.23 g (22 mmol) of triethylamine at 60 ° C. while stirring dripped.
- the reaction mixture is then stirred for a further hour at 60 ° C. and then concentrated under reduced pressure.
- the remaining residue is stirred with 35 ml of water and then suction filtered.
- the resulting, still moist solid is boiled with isopropanol, cooled to room temperature, suction filtered and dried.
- Triethylamine in 24 g of dimethylformamide is added dropwise at room temperature with stirring, a solution of 8.66 g (40 mmol) of 3,4-dichloroisothiazole-5-carboxylic acid chloride in 20 g of dimethylformamide.
- the reaction mixture is stirred at 20 ° C. for one hour.
- 6.67 g (56 mmol) of thionyl chloride are added dropwise to the resulting suspension with stirring.
- reaction mixture is stirred for a further 2 hours at room temperature, then 80 ml of water are added and the mixture is stirred for a further 15 minutes.
- the resulting solid is filtered off, washed twice with 40 ml of water and dried.
- the product obtained is boiled in 30 ml of isopropanol for 30 minutes. After cooling to room temperature, the resulting solid is suctioned off, twice with 10 ml each
- Triethylamine in 12 g of dimethylformamide is added dropwise at room temperature with stirring, a solution of 4.33 g (20 mmol) of 3,4-dichloroisothiazole-5-carboxylic acid chloride in 10 g of dimethylformamide.
- the reaction mixture is stirred at 20 ° C. for one hour.
- 4.3 g (28 mmol) of phosphorus oxychloride are added dropwise to the resulting suspension at 0 ° C. while stirring.
- the reaction mixture is stirred for a further 2 hours at 0 ° C., then mixed with 40 ml of water and stirred for a further 15 minutes.
- a solution of 8.66 g (40 mmol) of 3,4-dichloroisothiazole-5 is added to a solution of 6 g (44 mmol) of anthranilic acid amide and 4.46 g (44 mmol) of triethylamine in 24 g of dimethylformamide at room temperature with stirring -carboxylic acid chloride added dropwise in 20 g of dimethylformamide.
- the reaction mixture is stirred at 20 ° C. for one hour.
- 5.6 g (56 mmol) of phosgene are introduced into the resulting suspension at 20-25 ° C. with stirring.
- reaction mixture is stirred for a further 2 hours at room temperature, then 80 ml of water are added while cooling with ice and the mixture is stirred for a further 15 minutes.
- the resulting solid is filtered off, washed twice with 40 ml of water and dried. The received
- the aqueous phase is separated off from the two-phase filtrate and extracted twice with 150 ml of ethyl acetate each time.
- the combined organic phases are dried over sodium sulfate and then concentrated under reduced pressure.
- the remaining residue is stirred with 100 ml of petroleum ether and 25 ml of ethyl acetate.
- the resulting solid is filtered off, washed with ethyl acetate and dried.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Description
Claims
Priority Applications (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AU2003238510A AU2003238510A1 (en) | 2002-06-27 | 2003-06-17 | Method for producing 3,4-dichloro-n-(2-cyano-phenyl)-5-isothiazole carboxamide |
AT03732578T ATE308530T1 (de) | 2002-06-27 | 2003-06-17 | Verfahren zur herstellung von 3,4-dichlor-n-(2- cyano-phenyl)-5-isothiazolcarboxamid |
JP2004516609A JP4551762B2 (ja) | 2002-06-27 | 2003-06-17 | 3,4−ジクロロ−n−(2−シアノフェニル)−5−イソチアゾールカルボキサミドの製造方法 |
EP03732578A EP1519926B1 (de) | 2002-06-27 | 2003-06-17 | Verfahren zur herstellung von 3,4-dichlor-n-(2-cyano-phenyl)-5-isothiazolcarboxamid |
KR1020047021038A KR101069222B1 (ko) | 2002-06-27 | 2003-06-17 | 3,4-디클로로-n-(2-시아노-페닐)-5-이소티아졸카복사미드의 제조방법 |
DE50301572T DE50301572D1 (de) | 2002-06-27 | 2003-06-17 | Verfahren zur herstellung von 3,4-dichlor-n-(2-cyano-phenyl)-5-isothiazolcarboxamid |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE10228732.5 | 2002-06-27 | ||
DE10228732A DE10228732A1 (de) | 2002-06-27 | 2002-06-27 | Verfahren zur Herstellung von 3,4-Dichlor-N-(2-cyano-phenyl)-5-isothiazolcarboxamid |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2004002968A1 true WO2004002968A1 (de) | 2004-01-08 |
Family
ID=29723489
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2003/006360 WO2004002968A1 (de) | 2002-06-27 | 2003-06-17 | Verfahren zur herstellung von 3,4-dichlor-n-(2-cyano-phenyl)-5-isothiazolcarboxamid |
Country Status (9)
Country | Link |
---|---|
EP (1) | EP1519926B1 (de) |
JP (1) | JP4551762B2 (de) |
KR (1) | KR101069222B1 (de) |
CN (1) | CN1325483C (de) |
AT (1) | ATE308530T1 (de) |
AU (1) | AU2003238510A1 (de) |
DE (2) | DE10228732A1 (de) |
TW (1) | TWI266766B (de) |
WO (1) | WO2004002968A1 (de) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2007031146A1 (de) | 2005-07-29 | 2007-03-22 | Bayer Cropscience Aktiengesellschaft | Verfahren zur herstellung von 3,4-dichlor-n-(2-cyano-phenyl)-5-isothiazolcarboxamid |
CN103483287A (zh) * | 2013-10-12 | 2014-01-01 | 南开大学 | 一类含3,4-二氯异噻唑的双酰胺类化合物及其制备方法和用途 |
WO2018228984A1 (en) | 2017-06-14 | 2018-12-20 | Bayer Aktiengesellschaft | Process for preparing 3,4-dichloro-n-(2-cyanophenyl)-5-isothiazolecarboxamide |
WO2019192988A1 (de) | 2018-04-06 | 2019-10-10 | Bayer Aktiengesellschaft | Verfahren zur herstellung von 3,4-dichlor-n-(2-cyanophenyl)-5-isothiazolcarboxamid |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1999024413A2 (de) * | 1997-11-12 | 1999-05-20 | Bayer Aktiengesellschaft | Isothiazolcarbonsäureamide und deren verwendung zum schutz von pflanzen |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2115625B2 (de) * | 1971-03-31 | 1978-07-06 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Herstellung von N-o-Cyanophenyl-N', N'-disubstituierten Formamidinen und deren Salzen |
DE2115624A1 (de) * | 1971-03-31 | 1972-10-12 | Badische Anilin & Soda Fabrik AG, 6700 Ludwigshafen | Verfahren zur Herstellung von o Amino benzonitrilen |
-
2002
- 2002-06-27 DE DE10228732A patent/DE10228732A1/de not_active Withdrawn
-
2003
- 2003-06-17 WO PCT/EP2003/006360 patent/WO2004002968A1/de active IP Right Grant
- 2003-06-17 DE DE50301572T patent/DE50301572D1/de not_active Expired - Lifetime
- 2003-06-17 KR KR1020047021038A patent/KR101069222B1/ko active IP Right Grant
- 2003-06-17 AU AU2003238510A patent/AU2003238510A1/en not_active Abandoned
- 2003-06-17 AT AT03732578T patent/ATE308530T1/de not_active IP Right Cessation
- 2003-06-17 JP JP2004516609A patent/JP4551762B2/ja not_active Expired - Lifetime
- 2003-06-17 CN CNB038203294A patent/CN1325483C/zh not_active Expired - Lifetime
- 2003-06-17 EP EP03732578A patent/EP1519926B1/de not_active Expired - Lifetime
- 2003-06-26 TW TW092117350A patent/TWI266766B/zh not_active IP Right Cessation
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1999024413A2 (de) * | 1997-11-12 | 1999-05-20 | Bayer Aktiengesellschaft | Isothiazolcarbonsäureamide und deren verwendung zum schutz von pflanzen |
Cited By (19)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN105254582A (zh) * | 2005-07-29 | 2016-01-20 | 拜尔农作物科学股份公司 | 生产3,4-二氯-n-(2-氰基-苯基)-5-异噻唑羧酰胺的方法 |
JP2009502831A (ja) * | 2005-07-29 | 2009-01-29 | バイエル・クロツプサイエンス・アクチエンゲゼルシヤフト | 3,4−ジクロロ−n−(2−シアノフェニル)−5−イソチアゾールカルボキサミドを調製する方法 |
JP2013035846A (ja) * | 2005-07-29 | 2013-02-21 | Bayer Cropscience Ag | 3,4−ジクロロ−n−(2−シアノフェニル)−5−イソチアゾールカルボキサミドを調製する方法 |
EP2573077A1 (de) | 2005-07-29 | 2013-03-27 | Bayer CropScience AG | Verfahren zur Herstellung von 3,4-Dichlor-N-(2-cyano-phenyl)-5-isothiazolcarboxamid |
CN103087003A (zh) * | 2005-07-29 | 2013-05-08 | 拜尔农作物科学股份公司 | 生产3,4-二氯-n-(2-氰基-苯基)-5-异噻唑羧酰胺的方法 |
CN103102323A (zh) * | 2005-07-29 | 2013-05-15 | 拜尔农作物科学股份公司 | 生产3,4-二氯-n-(2-氰基-苯基)-5-异噻唑羧酰胺的方法 |
KR101332310B1 (ko) | 2005-07-29 | 2013-11-22 | 바이엘 크롭사이언스 아게 | 3,4-디클로로-n-(2-시아노페닐)-5-이소티아졸카복사미드의제조방법 |
CN105254582B (zh) * | 2005-07-29 | 2017-12-26 | 拜耳知识产权有限责任公司 | 生产3,4‑二氯‑n‑(2‑氰基‑苯基)‑5‑异噻唑羧酰胺的方法 |
WO2007031146A1 (de) | 2005-07-29 | 2007-03-22 | Bayer Cropscience Aktiengesellschaft | Verfahren zur herstellung von 3,4-dichlor-n-(2-cyano-phenyl)-5-isothiazolcarboxamid |
CN103483287B (zh) * | 2013-10-12 | 2015-07-08 | 南开大学 | 一类含3,4-二氯异噻唑的双酰胺类化合物及其制备方法和用途 |
CN103483287A (zh) * | 2013-10-12 | 2014-01-01 | 南开大学 | 一类含3,4-二氯异噻唑的双酰胺类化合物及其制备方法和用途 |
WO2018228984A1 (en) | 2017-06-14 | 2018-12-20 | Bayer Aktiengesellschaft | Process for preparing 3,4-dichloro-n-(2-cyanophenyl)-5-isothiazolecarboxamide |
CN110719908A (zh) * | 2017-06-14 | 2020-01-21 | 拜耳股份公司 | 用于制备3,4-二氯-n-(2-氰基苯基)-5-异噻唑甲酰胺的方法 |
US11220487B2 (en) | 2017-06-14 | 2022-01-11 | Bayer Aktiengesellschaft | Process for preparing 3,4-dichloro-n-(2-cyanophenyl)-5-isothiazolecarboxamide |
IL271148B (en) * | 2017-06-14 | 2022-08-01 | Bayer Ag | Process for preparing 4,3-dichloro-n-(2-cyanophenyl)-5-isothiazolecarboxamide |
TWI794243B (zh) * | 2017-06-14 | 2023-03-01 | 德商拜耳廠股份有限公司 | 製備3,4-二氯-n-(2-氰苯基)-5-異噻唑羧醯胺之方法 |
CN110719908B (zh) * | 2017-06-14 | 2023-05-26 | 拜耳股份公司 | 用于制备3,4-二氯-n-(2-氰基苯基)-5-异噻唑甲酰胺的方法 |
WO2019192988A1 (de) | 2018-04-06 | 2019-10-10 | Bayer Aktiengesellschaft | Verfahren zur herstellung von 3,4-dichlor-n-(2-cyanophenyl)-5-isothiazolcarboxamid |
US11339137B2 (en) | 2018-04-06 | 2022-05-24 | Bayer Aktiengesellschaft | Method for producing 3,4-dichloro-N-(2-cyanophenyl)-5-isothiazolecarboxamide |
Also Published As
Publication number | Publication date |
---|---|
KR20050008853A (ko) | 2005-01-21 |
JP4551762B2 (ja) | 2010-09-29 |
TW200409762A (en) | 2004-06-16 |
AU2003238510A1 (en) | 2004-01-19 |
DE10228732A1 (de) | 2004-01-15 |
DE50301572D1 (de) | 2005-12-08 |
TWI266766B (en) | 2006-11-21 |
EP1519926A1 (de) | 2005-04-06 |
KR101069222B1 (ko) | 2011-09-30 |
EP1519926B1 (de) | 2005-11-02 |
ATE308530T1 (de) | 2005-11-15 |
CN1678595A (zh) | 2005-10-05 |
CN1325483C (zh) | 2007-07-11 |
JP2005530847A (ja) | 2005-10-13 |
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