RU2012105122A - Способ получения хиральных производных 3-триазолилсульфоксида - Google Patents
Способ получения хиральных производных 3-триазолилсульфоксида Download PDFInfo
- Publication number
- RU2012105122A RU2012105122A RU2012105122/04A RU2012105122A RU2012105122A RU 2012105122 A RU2012105122 A RU 2012105122A RU 2012105122/04 A RU2012105122/04 A RU 2012105122/04A RU 2012105122 A RU2012105122 A RU 2012105122A RU 2012105122 A RU2012105122 A RU 2012105122A
- Authority
- RU
- Russia
- Prior art keywords
- carbon atoms
- alkyl
- hydrogen
- independently
- enantiomer
- Prior art date
Links
- YZXYLAXJHXMUPM-UHFFFAOYSA-N 1-(triazol-1-ylsulfinyl)triazole Chemical class C1=CN=NN1S(=O)N1C=CN=N1 YZXYLAXJHXMUPM-UHFFFAOYSA-N 0.000 title claims abstract 3
- 238000004519 manufacturing process Methods 0.000 title 1
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 48
- 125000000217 alkyl group Chemical group 0.000 claims abstract 31
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 24
- 239000001257 hydrogen Substances 0.000 claims abstract 24
- 150000002431 hydrogen Chemical class 0.000 claims abstract 14
- 238000000034 method Methods 0.000 claims abstract 14
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract 12
- 229910052731 fluorine Inorganic materials 0.000 claims abstract 12
- 239000011737 fluorine Substances 0.000 claims abstract 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract 6
- 229910052801 chlorine Inorganic materials 0.000 claims abstract 6
- 239000000460 chlorine Substances 0.000 claims abstract 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract 6
- 229910052736 halogen Inorganic materials 0.000 claims abstract 5
- 150000002367 halogens Chemical class 0.000 claims abstract 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract 4
- 229910052794 bromium Inorganic materials 0.000 claims abstract 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract 4
- 125000003118 aryl group Chemical group 0.000 claims abstract 3
- 239000003054 catalyst Substances 0.000 claims abstract 3
- 239000007800 oxidant agent Substances 0.000 claims abstract 3
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract 2
- 125000003545 alkoxy group Chemical group 0.000 claims 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 5
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 3
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims 3
- 125000005037 alkyl phenyl group Chemical group 0.000 claims 3
- 125000004966 cyanoalkyl group Chemical group 0.000 claims 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 2
- 239000003446 ligand Substances 0.000 claims 2
- 239000003960 organic solvent Substances 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000005243 carbonyl alkyl group Chemical group 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 238000002425 crystallisation Methods 0.000 claims 1
- 230000008025 crystallization Effects 0.000 claims 1
- -1 cyano, nitro, amino, hydroxy Chemical group 0.000 claims 1
- 125000004983 dialkoxyalkyl group Chemical group 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims 1
- 150000002978 peroxides Chemical class 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 229910052723 transition metal Inorganic materials 0.000 claims 1
- 150000003624 transition metals Chemical class 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- 125000001188 haloalkyl group Chemical group 0.000 abstract 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/12—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102009027771 | 2009-07-16 | ||
| DE102009027771.4 | 2009-07-16 | ||
| PCT/EP2010/004288 WO2011006646A1 (de) | 2009-07-16 | 2010-07-14 | Verfahren zur herstellung von chiralen 3-triazolyl-sulfoxid-derivaten |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| RU2012105122A true RU2012105122A (ru) | 2013-08-27 |
Family
ID=42710633
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2012105122/04A RU2012105122A (ru) | 2009-07-16 | 2010-07-14 | Способ получения хиральных производных 3-триазолилсульфоксида |
Country Status (14)
| Country | Link |
|---|---|
| US (3) | US8314133B2 (enExample) |
| EP (1) | EP2454242B1 (enExample) |
| JP (1) | JP5676602B2 (enExample) |
| KR (1) | KR20120037993A (enExample) |
| CN (1) | CN102471290B (enExample) |
| BR (1) | BR112012001078A8 (enExample) |
| DK (1) | DK2454242T3 (enExample) |
| ES (1) | ES2525535T3 (enExample) |
| IL (1) | IL217136A0 (enExample) |
| IN (1) | IN2012DN00422A (enExample) |
| MX (1) | MX2012000583A (enExample) |
| RU (1) | RU2012105122A (enExample) |
| TW (1) | TWI471314B (enExample) |
| WO (1) | WO2011006646A1 (enExample) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2274982A1 (de) * | 2009-07-16 | 2011-01-19 | Bayer CropScience AG | Verwendung von Phenyltriazolen zur Bekämpfung von Insekten und Spinnmilben durch Angiessen, Tröpfchen- oder Tauchapplikation oder durch Behandlung von Saatgut |
| CN102471290B (zh) | 2009-07-16 | 2016-02-03 | 拜耳知识产权有限责任公司 | 手性3-三唑基亚砜衍生物的制备方法 |
| US8242313B2 (en) | 2009-07-23 | 2012-08-14 | Bayer Cropscience Ag | Alkoxy enones and enamino ketones and a process for preparation thereof |
| JP5735962B2 (ja) * | 2009-07-23 | 2015-06-17 | バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツングＢａｙｅｒ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ ＧｍｂＨ | 新規なアルコキシエノンおよびエナミノケトンおよびその調製方法 |
| BR112012003698B1 (pt) * | 2009-08-20 | 2018-12-26 | Bayer Intellectual Property Gmbh | Compostos derivados de 3-[1-(3-haloalquil)-triazolil]-fenil-sulfeto, processos para preparação de compostos, compostos intermediários, composições, composiçõesagroquímicas e uso dos compostos e composições como acaricidas e inseticidas |
| WO2011020567A1 (de) * | 2009-08-20 | 2011-02-24 | Bayer Cropscience Ag | 3-triazolylphenyl-substituierte sulfid-derivate als akarizide und insektizide |
| BR112012030399A2 (pt) * | 2010-06-01 | 2020-10-20 | Kumiai Chemical Industry Co., Ltd. | composto de triazol com atividades pesticidas |
| EP2606726A1 (de) | 2011-12-21 | 2013-06-26 | Bayer CropScience AG | N-Arylamidine-substituierte trifluoroethylsulfid-Derivate als Akarizide und Insektizide |
| ES2625547T3 (es) | 2012-09-27 | 2017-07-19 | Bayer Cropscience Ag | Procedimiento de preparación de fenil y piridil pirrolidinas opcionalmente sustituidas |
| AR093909A1 (es) | 2012-12-12 | 2015-06-24 | Bayer Cropscience Ag | Uso de ingredientes activos para controlar nematodos en cultivos resistentes a nematodos |
| WO2015036380A1 (de) | 2013-09-13 | 2015-03-19 | Bayer Cropscience Ag | Verfahren zur reduktion von arylsulfoxiden zu arylthioethern |
| WO2015135984A1 (de) | 2014-03-13 | 2015-09-17 | Bayer Cropscience Ag | Verfahren zur herstellung von chiralen 3-(5-aminotriazolyl)-sulfoxid-derivaten |
| KR102625753B1 (ko) * | 2017-10-18 | 2024-01-17 | 바이엘 악티엔게젤샤프트 | 살곤충/살진드기 특성을 갖는 활성 화합물 조합물 |
| WO2021084074A1 (en) | 2019-10-30 | 2021-05-06 | Solvay Sa | Compositions and films comprising a polymer and tis2 particles, and their preparation and uses |
| MX2022012405A (es) | 2020-04-30 | 2023-01-11 | Kumiai Chemical Industry Co | Metodo para producir derivados de monosulfoxido. |
| CN116981659A (zh) | 2021-03-26 | 2023-10-31 | 拜耳公司 | 制备对映体富集的(2z)-2-(苯基亚氨基)-1,3-噻唑烷-4-酮亚砜衍生物的方法 |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE69934224T2 (de) | 1998-04-27 | 2007-10-04 | Kumiai Chemical Industry Co., Ltd. | 3-arylphenylsulfid-derivate und insektizide und mitizide |
| FR2863611B1 (fr) * | 2003-12-15 | 2006-03-24 | Sidem Pharma Sa | Procede de preparation enantioselective de derives de sulfoxydes |
| CA2520157A1 (fr) * | 2003-03-28 | 2004-10-14 | Sidem Pharma | Procede de preparation enantioselective de derives de sulfoxydes |
| FR2852956B1 (fr) * | 2003-03-28 | 2006-08-04 | Negma Gild | Procede de preparation enantioselective de derives de sulfoxydes |
| EP1516869A1 (en) * | 2003-09-19 | 2005-03-23 | Cephalon France | Process for enantioselective synthesis of single enantiomers of modafinil by asymmetric oxidation |
| FR2876101B1 (fr) * | 2004-10-05 | 2007-03-02 | Sidem Pharma Sa Sa | Procede de preparation enantioselective de derives de sulfoxydes |
| PL1802584T3 (pl) * | 2004-10-11 | 2010-03-31 | Ranbaxy Laboratories Ltd | Sposób wytwarzania podstawionych sulfotlenków |
| JP4970950B2 (ja) * | 2004-10-20 | 2012-07-11 | クミアイ化学工業株式会社 | ３−トリアゾリルフェニルスルフィド誘導体及びそれを有効成分として含有する殺虫・殺ダニ・殺線虫剤 |
| CN101012141B (zh) * | 2007-02-02 | 2012-05-23 | 沈阳药科大学 | 手性亚砜类化合物的制备方法 |
| CN103664811B (zh) * | 2007-11-30 | 2015-09-16 | 庵原化学工业株式会社 | (1h-1,2,4-三唑-1-基)芳基化合物及其制备方法 |
| CN101323582A (zh) * | 2008-07-30 | 2008-12-17 | 大连理工大学 | 一类手性西佛碱配体及其在硫醚不对称氧化反应中的应用 |
| CN101429192A (zh) * | 2008-08-22 | 2009-05-13 | 扬子江药业集团有限公司 | 生产手性亚砜衍生物的新方法 |
| CN102471290B (zh) | 2009-07-16 | 2016-02-03 | 拜耳知识产权有限责任公司 | 手性3-三唑基亚砜衍生物的制备方法 |
| EP2274982A1 (de) | 2009-07-16 | 2011-01-19 | Bayer CropScience AG | Verwendung von Phenyltriazolen zur Bekämpfung von Insekten und Spinnmilben durch Angiessen, Tröpfchen- oder Tauchapplikation oder durch Behandlung von Saatgut |
| BR112012003698B1 (pt) * | 2009-08-20 | 2018-12-26 | Bayer Intellectual Property Gmbh | Compostos derivados de 3-[1-(3-haloalquil)-triazolil]-fenil-sulfeto, processos para preparação de compostos, compostos intermediários, composições, composiçõesagroquímicas e uso dos compostos e composições como acaricidas e inseticidas |
| WO2011020567A1 (de) * | 2009-08-20 | 2011-02-24 | Bayer Cropscience Ag | 3-triazolylphenyl-substituierte sulfid-derivate als akarizide und insektizide |
-
2010
- 2010-07-14 CN CN201080031476.1A patent/CN102471290B/zh not_active Expired - Fee Related
- 2010-07-14 IN IN422DEN2012 patent/IN2012DN00422A/en unknown
- 2010-07-14 ES ES10732316.4T patent/ES2525535T3/es active Active
- 2010-07-14 RU RU2012105122/04A patent/RU2012105122A/ru not_active Application Discontinuation
- 2010-07-14 BR BR112012001078A patent/BR112012001078A8/pt active Search and Examination
- 2010-07-14 MX MX2012000583A patent/MX2012000583A/es active IP Right Grant
- 2010-07-14 DK DK10732316.4T patent/DK2454242T3/en active
- 2010-07-14 EP EP10732316.4A patent/EP2454242B1/de not_active Not-in-force
- 2010-07-14 JP JP2012519925A patent/JP5676602B2/ja not_active Expired - Fee Related
- 2010-07-14 KR KR1020127003961A patent/KR20120037993A/ko not_active Withdrawn
- 2010-07-14 WO PCT/EP2010/004288 patent/WO2011006646A1/de not_active Ceased
- 2010-07-15 TW TW99123228A patent/TWI471314B/zh not_active IP Right Cessation
- 2010-07-16 US US12/837,646 patent/US8314133B2/en not_active Expired - Fee Related
-
2011
- 2011-12-22 IL IL217136A patent/IL217136A0/en unknown
-
2012
- 2012-10-15 US US13/652,039 patent/US8765970B2/en not_active Expired - Fee Related
-
2014
- 2014-05-15 US US14/278,132 patent/US20140256953A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| CN102471290A (zh) | 2012-05-23 |
| US20110015405A1 (en) | 2011-01-20 |
| IN2012DN00422A (enExample) | 2015-05-15 |
| US20140256953A1 (en) | 2014-09-11 |
| TW201116517A (en) | 2011-05-16 |
| EP2454242B1 (de) | 2014-10-15 |
| WO2011006646A1 (de) | 2011-01-20 |
| BR112012001078A2 (pt) | 2015-09-01 |
| IL217136A0 (en) | 2012-02-29 |
| CN102471290B (zh) | 2016-02-03 |
| US8314133B2 (en) | 2012-11-20 |
| US8765970B2 (en) | 2014-07-01 |
| MX2012000583A (es) | 2012-02-13 |
| JP2012532906A (ja) | 2012-12-20 |
| US20130172573A1 (en) | 2013-07-04 |
| ES2525535T3 (es) | 2014-12-26 |
| KR20120037993A (ko) | 2012-04-20 |
| EP2454242A1 (de) | 2012-05-23 |
| TWI471314B (zh) | 2015-02-01 |
| JP5676602B2 (ja) | 2015-02-25 |
| BR112012001078A8 (pt) | 2016-05-03 |
| DK2454242T3 (en) | 2015-02-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FA92 | Acknowledgement of application withdrawn (lack of supplementary materials submitted) |
Effective date: 20141002 |