DE10228732A1 - 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
- DE10228732A1 DE10228732A1 DE10228732A DE10228732A DE10228732A1 DE 10228732 A1 DE10228732 A1 DE 10228732A1 DE 10228732 A DE10228732 A DE 10228732A DE 10228732 A DE10228732 A DE 10228732A DE 10228732 A1 DE10228732 A1 DE 10228732A1
- Authority
- DE
- Germany
- Prior art keywords
- dichloro
- phenyl
- formula
- stage
- cyano
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims abstract description 29
- WLPCAERCXQSYLQ-UHFFFAOYSA-N isotianil Chemical compound ClC1=NSC(C(=O)NC=2C(=CC=CC=2)C#N)=C1Cl WLPCAERCXQSYLQ-UHFFFAOYSA-N 0.000 title claims abstract description 17
- 238000002360 preparation method Methods 0.000 title claims description 3
- PXBFMLJZNCDSMP-UHFFFAOYSA-N 2-Aminobenzamide Chemical compound NC(=O)C1=CC=CC=C1N PXBFMLJZNCDSMP-UHFFFAOYSA-N 0.000 claims abstract description 12
- VSCBEYLFHZIKQA-UHFFFAOYSA-N n-(2-carbamoylphenyl)-3,4-dichloro-1,2-thiazole-5-carboxamide Chemical compound NC(=O)C1=CC=CC=C1NC(=O)C1=C(Cl)C(Cl)=NS1 VSCBEYLFHZIKQA-UHFFFAOYSA-N 0.000 claims abstract description 12
- MSSXWKAJMRSAGF-UHFFFAOYSA-N 3,4-dichloro-1,2-thiazole-5-carbonyl chloride Chemical compound ClC(=O)C=1SN=C(Cl)C=1Cl MSSXWKAJMRSAGF-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000003085 diluting agent Substances 0.000 claims abstract description 8
- 239000002253 acid Substances 0.000 claims abstract description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 66
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 8
- 239000012024 dehydrating agents Substances 0.000 claims description 6
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 6
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 4
- QQVDYSUDFZZPSU-UHFFFAOYSA-M chloromethylidene(dimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)=CCl QQVDYSUDFZZPSU-UHFFFAOYSA-M 0.000 claims description 3
- 238000005580 one pot reaction Methods 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 230000018044 dehydration Effects 0.000 abstract description 2
- 238000006297 dehydration reaction Methods 0.000 abstract description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 239000007787 solid Substances 0.000 description 23
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 18
- 239000011541 reaction mixture Substances 0.000 description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 238000003756 stirring Methods 0.000 description 12
- 239000000725 suspension Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 238000004128 high performance liquid chromatography Methods 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000000370 acceptor Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- HLCPWBZNUKCSBN-UHFFFAOYSA-N 2-aminobenzonitrile Chemical compound NC1=CC=CC=C1C#N HLCPWBZNUKCSBN-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
- NFDXQGNDWIPXQL-UHFFFAOYSA-N 1-cyclooctyldiazocane Chemical compound C1CCCCCCC1N1NCCCCCC1 NFDXQGNDWIPXQL-UHFFFAOYSA-N 0.000 description 2
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 2
- AVRPFRMDMNDIDH-UHFFFAOYSA-N 1h-quinazolin-2-one Chemical class C1=CC=CC2=NC(O)=NC=C21 AVRPFRMDMNDIDH-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 2
- 239000012973 diazabicyclooctane Substances 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- DRJAJMCZPUXJRO-UHFFFAOYSA-O (2-cyanoanilino)methylidene-dimethylazanium;hydrochloride Chemical compound Cl.C[N+](C)=CNC1=CC=CC=C1C#N DRJAJMCZPUXJRO-UHFFFAOYSA-O 0.000 description 1
- LMZWCNIRDVGDMH-UHFFFAOYSA-N 3,4-dichloro-2h-1,2-thiazole-3-carbonyl chloride Chemical compound ClC(=O)C1(Cl)NSC=C1Cl LMZWCNIRDVGDMH-UHFFFAOYSA-N 0.000 description 1
- WADSJYLPJPTMLN-UHFFFAOYSA-N 3-(cycloundecen-1-yl)-1,2-diazacycloundec-2-ene Chemical compound C1CCCCCCCCC=C1C1=NNCCCCCCCC1 WADSJYLPJPTMLN-UHFFFAOYSA-N 0.000 description 1
- HQQTZCPKNZVLFF-UHFFFAOYSA-N 4h-1,2-benzoxazin-3-one Chemical class C1=CC=C2ONC(=O)CC2=C1 HQQTZCPKNZVLFF-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical class NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 230000003641 microbiacidal effect Effects 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
- KDUUVCKHJZFVCQ-UHFFFAOYSA-N n-(2-carbamoylphenyl)-3,4-dichloro-2h-1,2-thiazole-3-carboxamide Chemical compound NC(=O)C1=CC=CC=C1NC(=O)C1(Cl)C(Cl)=CSN1 KDUUVCKHJZFVCQ-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 238000010626 work up procedure Methods 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10228732A DE10228732A1 (de) | 2002-06-27 | 2002-06-27 | 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 |
| 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 |
| EP03732578A EP1519926B1 (de) | 2002-06-27 | 2003-06-17 | Verfahren zur herstellung von 3,4-dichlor-n-(2-cyano-phenyl)-5-isothiazolcarboxamid |
| CNB038203294A CN1325483C (zh) | 2002-06-27 | 2003-06-17 | 制备3,4－二氯－n－(2－氰基苯基)－5－异噻唑羧酰胺的方法 |
| AT03732578T ATE308530T1 (de) | 2002-06-27 | 2003-06-17 | Verfahren zur herstellung von 3,4-dichlor-n-(2- cyano-phenyl)-5-isothiazolcarboxamid |
| PCT/EP2003/006360 WO2004002968A1 (de) | 2002-06-27 | 2003-06-17 | Verfahren zur herstellung von 3,4-dichlor-n-(2-cyano-phenyl)-5-isothiazolcarboxamid |
| AU2003238510A AU2003238510A1 (en) | 2002-06-27 | 2003-06-17 | Method for producing 3,4-dichloro-n-(2-cyano-phenyl)-5-isothiazole carboxamide |
| TW092117350A TWI266766B (en) | 2002-06-27 | 2003-06-26 | Process for preparing 3,4-dichloro-N-(2-cyanophenyl)-5-isothiazolecarboxamide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| 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 |
|---|---|
| DE10228732A1 true DE10228732A1 (de) | 2004-01-15 |
Family
ID=29723489
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE10228732A Withdrawn DE10228732A1 (de) | 2002-06-27 | 2002-06-27 | Verfahren zur Herstellung von 3,4-Dichlor-N-(2-cyano-phenyl)-5-isothiazolcarboxamid |
| DE50301572T Expired - Lifetime DE50301572D1 (de) | 2002-06-27 | 2003-06-17 | Verfahren zur herstellung von 3,4-dichlor-n-(2-cyano-phenyl)-5-isothiazolcarboxamid |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE50301572T Expired - Lifetime DE50301572D1 (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 (https=) |
| JP (1) | JP4551762B2 (https=) |
| KR (1) | KR101069222B1 (https=) |
| CN (1) | CN1325483C (https=) |
| AT (1) | ATE308530T1 (https=) |
| AU (1) | AU2003238510A1 (https=) |
| DE (2) | DE10228732A1 (https=) |
| TW (1) | TWI266766B (https=) |
| WO (1) | WO2004002968A1 (https=) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102005035617A1 (de) * | 2005-07-29 | 2007-02-15 | Bayer Cropscience Ag | 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 |
| 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 |
Family Cites Families (3)
| 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 |
| DE19750012A1 (de) * | 1997-11-12 | 1999-05-20 | Bayer Ag | Isothiazolcarbonsäureamide |
-
2002
- 2002-06-27 DE DE10228732A patent/DE10228732A1/de not_active Withdrawn
-
2003
- 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 AU AU2003238510A patent/AU2003238510A1/en not_active Abandoned
- 2003-06-17 KR KR1020047021038A patent/KR101069222B1/ko not_active Expired - Lifetime
- 2003-06-17 CN CNB038203294A patent/CN1325483C/zh not_active Expired - Lifetime
- 2003-06-17 WO PCT/EP2003/006360 patent/WO2004002968A1/de not_active Ceased
- 2003-06-17 DE DE50301572T patent/DE50301572D1/de 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
Also Published As
| Publication number | Publication date |
|---|---|
| JP2005530847A (ja) | 2005-10-13 |
| CN1325483C (zh) | 2007-07-11 |
| DE50301572D1 (de) | 2005-12-08 |
| AU2003238510A1 (en) | 2004-01-19 |
| TWI266766B (en) | 2006-11-21 |
| EP1519926A1 (de) | 2005-04-06 |
| EP1519926B1 (de) | 2005-11-02 |
| ATE308530T1 (de) | 2005-11-15 |
| CN1678595A (zh) | 2005-10-05 |
| WO2004002968A1 (de) | 2004-01-08 |
| JP4551762B2 (ja) | 2010-09-29 |
| KR101069222B1 (ko) | 2011-09-30 |
| TW200409762A (en) | 2004-06-16 |
| KR20050008853A (ko) | 2005-01-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8139 | Disposal/non-payment of the annual fee |