AR074328A1 - Proceso para la fabricacion de bromuros de 3- piridilmetil amonio sustituidos - Google Patents
Proceso para la fabricacion de bromuros de 3- piridilmetil amonio sustituidosInfo
- Publication number
- AR074328A1 AR074328A1 ARP090104386A ARP090104386A AR074328A1 AR 074328 A1 AR074328 A1 AR 074328A1 AR P090104386 A ARP090104386 A AR P090104386A AR P090104386 A ARP090104386 A AR P090104386A AR 074328 A1 AR074328 A1 AR 074328A1
- Authority
- AR
- Argentina
- Prior art keywords
- hydrogen
- formula
- dichlorobenzene
- optionally substituted
- alkyl
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- 238000000034 method Methods 0.000 title abstract 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 title 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 4
- -1 5,6-disubstituted-3-pyridylmethyl ammonium bromides Chemical class 0.000 abstract 4
- 229910052739 hydrogen Inorganic materials 0.000 abstract 4
- 239000001257 hydrogen Substances 0.000 abstract 4
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 abstract 3
- 239000002904 solvent Substances 0.000 abstract 3
- 239000008346 aqueous phase Substances 0.000 abstract 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 2
- 229910052794 bromium Inorganic materials 0.000 abstract 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 125000005843 halogen group Chemical group 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- 150000002431 hydrogen Chemical class 0.000 abstract 2
- 239000012074 organic phase Substances 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 abstract 1
- ZPQOPVIELGIULI-UHFFFAOYSA-N 1,3-dichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1 ZPQOPVIELGIULI-UHFFFAOYSA-N 0.000 abstract 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 150000004982 aromatic amines Chemical class 0.000 abstract 1
- 229950005499 carbon tetrachloride Drugs 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- 125000004122 cyclic group Chemical group 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 239000003999 initiator Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- WYROLENTHWJFLR-ACLDMZEESA-N queuine Chemical compound C1=2C(=O)NC(N)=NC=2NC=C1CN[C@H]1C=C[C@H](O)[C@@H]1O WYROLENTHWJFLR-ACLDMZEESA-N 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- 150000003512 tertiary amines Chemical class 0.000 abstract 1
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
- C07D213/80—Acids; Esters in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Reivindicación 1: Un proceso para la fabricación de bromuros de 5,6-disustituido-3-piridilmetil amonio (1), en donde Q es una amina terciaria, alifática o cíclica, saturada, parcialmente no saturada o aromática; Z es hidrógeno o halógeno; Z1 es hidrógeno, halógeno, ciano o nitro; Y e Y1 son cada uno, independientemente, OR1, NR1R2 o, cuando se toman en forma conjunta, YY1 es -O-, -S- o NR3-; R1 y R2 son cada uno, independientemente, hidrógeno, alquilo C1-4, opcionalmente sustituido con alcoxi C1-4 o fenilo opcionalmente sustituido con uno a tres grupos alquilo C1-4, grupos alcoxi C1-4 o átomos de halógeno, o fenilo opcionalmente sustituido con uno a tres grupos alquilo C1-4, grupos alcoxi C1-4 o átomos de halógeno; R3 es hidrógeno o alquilo C1-4; caracterizado porque comprende las etapas de: (i) hacer reaccionar un compuesto de la fórmula (2), en donde los símbolos tienen el significado que se les otorga en la fórmula (1), con bromo en presencia de un iniciador radical en una mezcla de solvente que comprende una fase acuosa y una fase orgánica, donde la fase orgánica comprende un solvente seleccionado de 1,2-dicloroetano, clorobenceno, 1,2-diclorobenceno, 1,3-diclorobenceno, 1,4-diclorobenceno y tetraclorometano, y donde el valor de pH de la fase acuosa es de 3 a < 8, para obtener un compuesto 3-bromometil-5,6-disustituido piridina (3) en donde Y, Y1, Z y Z1 tienen los significados otorgados en la fórmula (1), y (ii) hacer reaccionar el compuesto bromo de la fórmula (3) con una base amina terciaria Q en un solvente en un rango de temperatura de 0sC a 100sC.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11423008P | 2008-11-13 | 2008-11-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR074328A1 true AR074328A1 (es) | 2011-01-05 |
Family
ID=41572415
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP090104386A AR074328A1 (es) | 2008-11-13 | 2009-11-13 | Proceso para la fabricacion de bromuros de 3- piridilmetil amonio sustituidos |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US9096570B2 (es) |
| EP (1) | EP2365965B1 (es) |
| JP (1) | JP5713914B2 (es) |
| CN (1) | CN102245576B (es) |
| AR (1) | AR074328A1 (es) |
| AU (1) | AU2009315580B2 (es) |
| BR (1) | BRPI0921882B1 (es) |
| IL (1) | IL212808A (es) |
| MX (1) | MX2011004938A (es) |
| RU (1) | RU2549896C2 (es) |
| TW (1) | TW201029975A (es) |
| UA (1) | UA103502C2 (es) |
| UY (1) | UY32243A (es) |
| WO (1) | WO2010055139A1 (es) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010054952A1 (en) | 2008-11-13 | 2010-05-20 | Basf Se | 2-[(1-cyanopropyl)carbamoyl]-5-chloromethyl nicotinic acids and the use thereof in manufacturing herbicidal imidazolinones |
| EP2358678B1 (en) | 2008-11-13 | 2015-01-14 | Basf Se | Process for manufacturing 5-chloromethyl-2,3-pyridine dicarboxylic acid anhydrides |
| DK2982673T3 (en) | 2008-12-09 | 2018-06-06 | Basf Se | PROCEDURE FOR PREPARING 5-CHLORMETHYLPYRIDINE-2,3-DICARBOXYLYAIC ANHYRIDE |
| CN103613535A (zh) * | 2013-11-26 | 2014-03-05 | 潍坊先达化工有限公司 | 一种5-（甲氧基甲基）-2,3-吡啶二甲酸二甲酯的合成方法 |
| CN110234628B (zh) * | 2016-11-21 | 2024-05-17 | 阿达玛阿甘有限公司 | 制备甲氧基甲基吡啶二甲酸酯的方法 |
| CN107033067A (zh) * | 2017-06-25 | 2017-08-11 | 刘瑞海 | 一种2‑甲氧基甲基吡啶的合成方法 |
| CN107151228A (zh) * | 2017-06-25 | 2017-09-12 | 刘瑞海 | 一种3‑甲氧基甲基吡啶的合成方法 |
| CN107286081A (zh) * | 2017-06-26 | 2017-10-24 | 蒋潇 | 一种4‑甲氧基甲基吡啶的合成方法 |
| CN109096294A (zh) * | 2018-09-03 | 2018-12-28 | 周银平 | 吡啶化合物的制备方法 |
| EP3782985A1 (en) | 2019-08-19 | 2021-02-24 | BASF Agrochemical Products B.V. | Process for manufacturing 5-methoxymethylpyridine-2,3-dicarboxylic acid derivatives |
| CN113968814A (zh) * | 2020-07-22 | 2022-01-25 | 帕潘纳(北京)科技有限公司 | 一种制备5-溴甲基-2,3-吡啶羧酸二甲酯的方法 |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3330604A1 (de) | 1983-08-25 | 1985-03-28 | Hoechst Ag, 6230 Frankfurt | Verfahren zur herstellung von brommethylthiophen-carbonsaeureestern |
| US4562257A (en) | 1983-11-07 | 1985-12-31 | American Cyanamid Company | Preparation of substituted and unsubstituted 2-carbamoyl nicotinic and 3-quinolinecarboxylic acids |
| US4782157A (en) * | 1984-12-03 | 1988-11-01 | American Cyanamid Co. | Preparation of substituted and unsubstituted 2-carbamoyl nicotinic and 3-quinolinecarboxylic acids |
| JPH07611B2 (ja) | 1986-01-24 | 1995-01-11 | 日産化学工業株式会社 | ピリジン誘導体，その製造方法および除草剤 |
| US5334576A (en) | 1986-07-28 | 1994-08-02 | American Cyanamid Company | 5 (and/or 6) substituted 2-(2-imidazolin-2-yl)nicotinic acids, esters and salts, useful as herbicidal agents and novel intermediates for the preparation of said nicotinic acids, esters and salts |
| EP0322616A3 (en) | 1987-12-31 | 1989-10-18 | American Cyanamid Company | Novel 5(and/or 6)substituted 2-(2-imidazolin-2-yl)nicotinic acids, esters and salts, useful as herbicidal agents and nivel intermediates for the preparation of said nicotinic acids, esters and salts |
| US5026859A (en) | 1989-12-27 | 1991-06-25 | American Cyanamid Company | Alkyl esters of 5-heterocyclic-pyridine-2,3-dicarboxylic acids |
| US5215568A (en) | 1991-10-31 | 1993-06-01 | American Cyanamid Company | Oxime derivatives of formylpyridyl imidazolinones, the herbicidal use and methods for the preparation thereof |
| US5288866A (en) * | 1991-12-20 | 1994-02-22 | American Cyanamid Company | 5,6-disubstituted-3-pyridylmethyl ammonium halide compounds useful for the preparation of 5- (substituted methyl)-2,3-pyridinedicarboxylic acids |
| CN1042333C (zh) * | 1992-10-14 | 1999-03-03 | 美国氰胺公司 | 5,6－二取代－3－吡啶甲基卤化铵类化合物及其制备方法 |
| ES2164211T3 (es) | 1995-06-05 | 2002-02-16 | Basf Ag | Procedimiento mejorado para la fabricacion de sal de 5-(alcoximetil)piridin-2,3-dicarboxilato. |
| US5892050A (en) | 1998-01-28 | 1999-04-06 | American Cyanamid Company | Process for the preparation of pyridine dicarboxylate derivatives |
| US6339158B1 (en) * | 1999-05-03 | 2002-01-15 | American Cyanamid Co. | Process for the preparation of chiral nicotinic, quinolinic or benzoic acid imidazolinone herbicides |
| EP2145682A1 (de) | 2008-07-18 | 2010-01-20 | Roche Diagnostics GmbH | Testelement zur Analyse einer Körperflüssigkeitsprobe auf einen darin enthaltenen Analyten, Analysesystem und Verfahren zur Steuerung der Bewegung einer in einem Kanal eines Testelements enthaltenen Flüssigkeit |
| WO2010054952A1 (en) | 2008-11-13 | 2010-05-20 | Basf Se | 2-[(1-cyanopropyl)carbamoyl]-5-chloromethyl nicotinic acids and the use thereof in manufacturing herbicidal imidazolinones |
| EP2358678B1 (en) | 2008-11-13 | 2015-01-14 | Basf Se | Process for manufacturing 5-chloromethyl-2,3-pyridine dicarboxylic acid anhydrides |
| WO2010055042A1 (en) | 2008-11-13 | 2010-05-20 | Basf Se | 2-[(1-cyanopropyl)carbamoyl]-5-methoxymethyl nicotinic acids and the use thereof in manufacturing herbicidal imidazolinones |
-
2009
- 2009-11-13 EP EP09755886.0A patent/EP2365965B1/en active Active
- 2009-11-13 US US13/128,787 patent/US9096570B2/en active Active
- 2009-11-13 UY UY0001032243A patent/UY32243A/es unknown
- 2009-11-13 TW TW098138732A patent/TW201029975A/zh unknown
- 2009-11-13 UA UAA201107340A patent/UA103502C2/ru unknown
- 2009-11-13 BR BRPI0921882-3A patent/BRPI0921882B1/pt active IP Right Grant
- 2009-11-13 JP JP2011536030A patent/JP5713914B2/ja active Active
- 2009-11-13 WO PCT/EP2009/065155 patent/WO2010055139A1/en not_active Ceased
- 2009-11-13 CN CN200980149745.1A patent/CN102245576B/zh active Active
- 2009-11-13 AU AU2009315580A patent/AU2009315580B2/en active Active
- 2009-11-13 MX MX2011004938A patent/MX2011004938A/es active IP Right Grant
- 2009-11-13 AR ARP090104386A patent/AR074328A1/es active IP Right Grant
- 2009-11-13 RU RU2011123372/04A patent/RU2549896C2/ru active
-
2011
- 2011-05-11 IL IL212808A patent/IL212808A/en active IP Right Grant
Also Published As
| Publication number | Publication date |
|---|---|
| JP2012508729A (ja) | 2012-04-12 |
| EP2365965B1 (en) | 2019-01-09 |
| IL212808A0 (en) | 2011-07-31 |
| RU2549896C2 (ru) | 2015-05-10 |
| MX2011004938A (es) | 2011-06-06 |
| US20110224433A1 (en) | 2011-09-15 |
| CN102245576B (zh) | 2014-11-05 |
| TW201029975A (en) | 2010-08-16 |
| UA103502C2 (ru) | 2013-10-25 |
| IL212808A (en) | 2015-10-29 |
| WO2010055139A1 (en) | 2010-05-20 |
| BRPI0921882A2 (pt) | 2015-12-29 |
| AU2009315580B2 (en) | 2015-06-18 |
| BRPI0921882B1 (pt) | 2018-02-06 |
| US9096570B2 (en) | 2015-08-04 |
| UY32243A (es) | 2010-05-31 |
| JP5713914B2 (ja) | 2015-05-07 |
| CN102245576A (zh) | 2011-11-16 |
| AU2009315580A1 (en) | 2010-05-20 |
| RU2011123372A (ru) | 2012-12-20 |
| EP2365965A1 (en) | 2011-09-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FG | Grant, registration |