AR018190A1 - Proceso mejorado para la preparacion de derivados de n-(1-cianoalquil)-2-fenoxipropionamida - Google Patents
Proceso mejorado para la preparacion de derivados de n-(1-cianoalquil)-2-fenoxipropionamidaInfo
- Publication number
- AR018190A1 AR018190A1 ARP990101806A ARP990101806A AR018190A1 AR 018190 A1 AR018190 A1 AR 018190A1 AR P990101806 A ARP990101806 A AR P990101806A AR P990101806 A ARP990101806 A AR P990101806A AR 018190 A1 AR018190 A1 AR 018190A1
- Authority
- AR
- Argentina
- Prior art keywords
- formula
- derivatives
- compound
- product
- phenoxypropionamide
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 6
- 239000002585 base Substances 0.000 abstract 3
- 239000006227 byproduct Substances 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- 239000000047 product Substances 0.000 abstract 3
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 abstract 2
- 230000015572 biosynthetic process Effects 0.000 abstract 2
- 230000000855 fungicidal effect Effects 0.000 abstract 2
- 239000000417 fungicide Substances 0.000 abstract 2
- -1 halide compound Chemical class 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 238000004519 manufacturing process Methods 0.000 abstract 2
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical class CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 abstract 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- SXERGJJQSKIUIC-UHFFFAOYSA-N 2-Phenoxypropionic acid Chemical compound OC(=O)C(C)OC1=CC=CC=C1 SXERGJJQSKIUIC-UHFFFAOYSA-N 0.000 abstract 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 abstract 1
- 150000008041 alkali metal carbonates Chemical class 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 125000005219 aminonitrile group Chemical group 0.000 abstract 1
- 238000011109 contamination Methods 0.000 abstract 1
- 239000006184 cosolvent Substances 0.000 abstract 1
- 238000012272 crop production Methods 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 230000001627 detrimental effect Effects 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 230000002363 herbicidal effect Effects 0.000 abstract 1
- 239000002085 irritant Substances 0.000 abstract 1
- 231100000021 irritant Toxicity 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 230000003287 optical effect Effects 0.000 abstract 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 abstract 1
- 231100000208 phytotoxic Toxicity 0.000 abstract 1
- 230000000885 phytotoxic effect Effects 0.000 abstract 1
- 238000011084 recovery Methods 0.000 abstract 1
- 125000005270 trialkylamine group Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
- C07C237/20—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Un proceso para la preparacion de un compuesto de la formula (I) donde R1 y R2 son cada uno independientemente H, halogeno, alquilo C1-6 o haloalquiloC1-6; R3 es H o alquilo C1-4; y R4 y R5 son independientemente H, alquilo C1-6, haloalquilo C1-6 o cicloalquilo C1-6; y sus isomeros opticos, que comprendehacer reaccionar al compuesto de haluro de ácido fenoxi de la formula (II), donde X es halogeno y R1, R2 y R3 son como se describimos para la formula (I) conal menos un equivalente molar de un compuesto de amino nitrilo de la formula (III) donde R4 y R5 son como describimos para la formula (I) ante la presencia deun carbonato de metal alcalino acuoso o bicarbonato de metal alcalino acuoso o sus mezclas, opcionalmente ante la presencia de unco-solvente. En general, losprocesos conocidos para preparar a los derivados del fungicida N-(1-cianoalquil)-2-fenoxipropionamida provocan un sistema no acuoso que utiliza una base deamina orgánica, como por ejemplo trialquilamina. Sin embargo, al fabricar en escala, el uso de irritantes como por ejemplo aminas orgánicas volátiles provocauna gran cantidad de afluente que requiere un tratamiento costoso y pasos de recuperacion. Un proceso alternativo para preparar dichos derivados depropionamidautiliza NaOH acuoso al 10% como base. Sin embargo, el uso de una base fuerte como por ejemplo NaOH aumenta la velocidad de formacion desubproductos no deseados como por ejemplo la formacion de ácido fenoxipropionico correspondiente del cloruro de ácido de partida. Este subproducto no deseadono es transportado en el producto de amida deseado. Más aun, dicho subproducto es un derivado herbicida conocido y podría, por lo tanto, contaminar el productofungicida deseado con un compuesto fitotoxico. Esta contaminacion sería perjudicial para el uso del producto en la práctica de la produccion de cultivos. Porlo tanto, se proporciona un proceso mejorado, economico y eficiente para la preparacion de los derivados de N-(1-cianoalquil)-2-fenoxipropionamida. Dichosderivados de propionamida se producen con un rendimiento mayor y una pureza mejoradas.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/062,975 US5942640A (en) | 1998-04-20 | 1998-04-20 | Process for the manufacture of N-(1-cyanoalkyl)-2-phenoxypropionamide derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR018190A1 true AR018190A1 (es) | 2001-10-31 |
Family
ID=22046082
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP990101806A AR018190A1 (es) | 1998-04-20 | 1999-04-19 | Proceso mejorado para la preparacion de derivados de n-(1-cianoalquil)-2-fenoxipropionamida |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US5942640A (es) |
| EP (1) | EP1071659A1 (es) |
| JP (1) | JP2002512217A (es) |
| KR (1) | KR20010071161A (es) |
| CN (1) | CN1298384A (es) |
| AR (1) | AR018190A1 (es) |
| AU (1) | AU3382499A (es) |
| BR (1) | BR9909759A (es) |
| CA (1) | CA2328723A1 (es) |
| CO (1) | CO4810332A1 (es) |
| EA (1) | EA200001020A1 (es) |
| HU (1) | HUP0101750A2 (es) |
| IL (1) | IL138843A0 (es) |
| NZ (1) | NZ507532A (es) |
| PL (1) | PL343629A1 (es) |
| SK (1) | SK14772000A3 (es) |
| WO (1) | WO1999054287A1 (es) |
| ZA (1) | ZA200006713B (es) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2001511147A (ja) * | 1997-02-04 | 2001-08-07 | ザ・ボード・オブ・トラステイーズ・オブ・ザ・ユニバーシテイ・オブ・アーカンソー | 殺菌・殺カビ性のカルボキサミド類 |
| DE19947613A1 (de) * | 1998-10-07 | 2000-04-13 | Sumitomo Chemical Co | Cyanatreinigungsverfahren |
| EP1155010A1 (en) * | 1999-02-20 | 2001-11-21 | AstraZeneca AB | Acetamido acetonitrile derivatives as inhibitors of cathepsin l and/or cathepsin s |
| BR0210912A (pt) * | 2001-06-01 | 2004-08-31 | Axys Pharm Inc | Compostos e composições como inibidores de catepsina |
| CN106366020B (zh) * | 2016-08-31 | 2018-12-11 | 京博农化科技股份有限公司 | 一种合成手性稻瘟酰胺的方法 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA992988A (en) * | 1971-06-25 | 1976-07-13 | Don R. Baker | N-(1,1 SUBSTITUTED ACETONITRILO)-.alpha.-(3,5-SUBSTITUTED PHENOXY) ALKYL AMIDES AND THEIR USE AS HERBICIDES |
| US3932168A (en) * | 1971-11-17 | 1976-01-13 | Abbott Laboratories | Substituted aryloxyacetamido nitrile derivatives as carbohydrate deposition agents |
| US4052432A (en) * | 1974-11-18 | 1977-10-04 | Stauffer Chemical Company | N-(1,1 Substituted acetonitrilo)-α-(3,5-substituted phenoxy) alkyl amides |
| US4087277A (en) * | 1976-05-20 | 1978-05-02 | Stauffer Chemical Company | N-(1,1-substituted acetonitrilo)-α-(3,5-substituted phenoxy) alkyl amides and their use as herbicides |
| AR220917A1 (es) * | 1977-10-26 | 1980-12-15 | Stauffer Chemical Co | Compuestos de n-sustituido-2-(4 sustituido-3,5-dimetilfenoxi)butiramida utiles como anublicidas y composicion que los contiene |
| FR2446812A1 (fr) * | 1979-01-16 | 1980-08-14 | Produits Ind Cie Fse | Phenoxy- et thiophenoxynitriles et leurs applications en tant qu'herbicides |
| DE3629441A1 (de) * | 1986-08-29 | 1988-03-03 | Celamerck Gmbh & Co Kg | Neue phenoxycarbonsaeurederivate, ihre herstellung und verwendung |
| JPH059165A (ja) * | 1991-02-18 | 1993-01-19 | Mitsubishi Petrochem Co Ltd | 置換フエノキシカルボン酸アミド誘導体 |
| JPH0570428A (ja) * | 1991-09-13 | 1993-03-23 | Mitsubishi Petrochem Co Ltd | 置換フエノキシカルボン酸アミド誘導体およびそれを含有する農業用殺菌剤 |
-
1998
- 1998-04-20 US US09/062,975 patent/US5942640A/en not_active Expired - Fee Related
-
1999
- 1999-04-05 WO PCT/US1999/007443 patent/WO1999054287A1/en not_active Ceased
- 1999-04-05 AU AU33824/99A patent/AU3382499A/en not_active Abandoned
- 1999-04-05 CN CN99805292A patent/CN1298384A/zh active Pending
- 1999-04-05 PL PL99343629A patent/PL343629A1/xx unknown
- 1999-04-05 EA EA200001020A patent/EA200001020A1/ru unknown
- 1999-04-05 JP JP2000544628A patent/JP2002512217A/ja active Pending
- 1999-04-05 BR BR9909759-1A patent/BR9909759A/pt not_active IP Right Cessation
- 1999-04-05 KR KR1020007011599A patent/KR20010071161A/ko not_active Abandoned
- 1999-04-05 IL IL13884399A patent/IL138843A0/xx unknown
- 1999-04-05 HU HU0101750A patent/HUP0101750A2/hu unknown
- 1999-04-05 CA CA002328723A patent/CA2328723A1/en not_active Abandoned
- 1999-04-05 NZ NZ507532A patent/NZ507532A/xx unknown
- 1999-04-05 EP EP99915270A patent/EP1071659A1/en not_active Withdrawn
- 1999-04-05 SK SK1477-2000A patent/SK14772000A3/sk unknown
- 1999-04-15 CO CO99022531A patent/CO4810332A1/es unknown
- 1999-04-19 AR ARP990101806A patent/AR018190A1/es not_active Application Discontinuation
-
2000
- 2000-11-17 ZA ZA200006713A patent/ZA200006713B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ZA200006713B (en) | 2001-11-19 |
| KR20010071161A (ko) | 2001-07-28 |
| EP1071659A1 (en) | 2001-01-31 |
| CN1298384A (zh) | 2001-06-06 |
| SK14772000A3 (sk) | 2002-05-09 |
| US5942640A (en) | 1999-08-24 |
| CO4810332A1 (es) | 1999-06-30 |
| JP2002512217A (ja) | 2002-04-23 |
| EA200001020A1 (ru) | 2001-06-25 |
| WO1999054287A1 (en) | 1999-10-28 |
| IL138843A0 (en) | 2001-10-31 |
| PL343629A1 (en) | 2001-08-27 |
| HUP0101750A2 (hu) | 2001-10-28 |
| AU3382499A (en) | 1999-11-08 |
| BR9909759A (pt) | 2000-12-19 |
| CA2328723A1 (en) | 1999-10-28 |
| NZ507532A (en) | 2002-08-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FA | Abandonment or withdrawal |