AR111269A1 - Producción de compuestos de arilpirrol en presencia de una base de dipea - Google Patents
Producción de compuestos de arilpirrol en presencia de una base de dipeaInfo
- Publication number
- AR111269A1 AR111269A1 ARP180100571A ARP180100571A AR111269A1 AR 111269 A1 AR111269 A1 AR 111269A1 AR P180100571 A ARP180100571 A AR P180100571A AR P180100571 A ARP180100571 A AR P180100571A AR 111269 A1 AR111269 A1 AR 111269A1
- Authority
- AR
- Argentina
- Prior art keywords
- compounds
- formula
- production
- diisopropylethylamine
- variables
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title abstract 10
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 title abstract 8
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 abstract 4
- 238000000034 method Methods 0.000 abstract 3
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 2
- 229910019213 POCl3 Inorganic materials 0.000 abstract 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 abstract 1
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- QQVDYSUDFZZPSU-UHFFFAOYSA-M chloromethylidene(dimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)=CCl QQVDYSUDFZZPSU-UHFFFAOYSA-M 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members 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
- C07D207/36—Oxygen or sulfur atoms
- C07D207/40—2,5-Pyrrolidine-diones
- C07D207/416—2,5-Pyrrolidine-diones 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 other ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/33—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/337—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyrrole Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
Reivindicación 1: El proceso A caracterizado porque es para la producción de los compuestos de la fórmula (1), en donde las variables tienen el siguiente significado R¹ es fenilo, sustituido con ninguno, uno o más R¹¹ iguales o diferentes; R¹¹ es F, Cl, Br, l, CN, NO₂, OH, C₁₋₄-alquilo, C₁₋₄-haloalquilo, C₁₋₄-alcoxi, C₁₋₄-haloalcoxi, C₁₋₄-alquil-C(O)O, C₁₋₄-haloalquil-C(O)O; o dos sustituyentes R¹¹ situados en átomos del anillo de fenilo adyacentes juntos son un grupo -OCH₂O-, -OCF₂O, o -CH=CH-CH=CH-, y forman, junto con los átomos de carbono a los que están unidos un anillo de 5 a 6 miembros; y n es 1, 2 ó 3; que comprende la etapa A de hacer reaccionar los compuestos de la fórmula (2) en donde las variables tienen el mismo significado que se define para los compuestos de la fórmula (1); con 2,3-dihalopropionitrilo o 2-haloacrilonitrilo en presencia de diisopropiletilamina. Reivindicación 4: El proceso B caracterizado porque es para la producción de los compuestos de la fórmula (3), en donde las variables tienen un significado como se define para los compuesto de la fórmula (1); que comprende la etapa B de hacer reaccionar compuestos de la fórmula (1) con Br₂ en presencia de diisopropiletilamina. Reivindicación 9: El proceso C caracterizado porque es para la producción de los compuestos de la fórmula (4), en donde R¹ y n son como se definen para los compuestos de la fórmula (1), en donde R² es C₁₋₄-alcoximetilo; que comprende la etapa C de hacer reaccionar compuestos de la fórmula (3) con di(C₁₋₄-alcoxi) metano, y POCl₃ o una mezcla que comprende POCl₃ y DMF (reactivo de Vilsmeier), en presencia de diisopropiletilamina.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP17160466 | 2017-03-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR111269A1 true AR111269A1 (es) | 2019-06-26 |
Family
ID=58358355
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP180100571A AR111269A1 (es) | 2017-03-13 | 2018-03-12 | Producción de compuestos de arilpirrol en presencia de una base de dipea |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US11584716B2 (es) |
| JP (2) | JP7260480B2 (es) |
| KR (1) | KR102623135B1 (es) |
| CN (1) | CN110382462A (es) |
| AR (1) | AR111269A1 (es) |
| CA (1) | CA3053443A1 (es) |
| IL (1) | IL268864B (es) |
| MX (1) | MX2019010998A (es) |
| WO (1) | WO2018166819A1 (es) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109438315A (zh) * | 2018-11-14 | 2019-03-08 | 江苏宝众宝达药业有限公司 | 一种虫螨腈的制备方法 |
| CN112608268A (zh) * | 2020-12-22 | 2021-04-06 | 李通 | 一种溶剂dmf替代乙腈生产溴虫腈中间体吡咯的方法 |
| CN114436932A (zh) * | 2022-01-12 | 2022-05-06 | 山东潍坊双星农药有限公司 | 一种溴虫腈同系物的合成工艺 |
| CN114573494B (zh) * | 2022-04-14 | 2024-03-15 | 山东潍坊双星农药有限公司 | 一种溴虫腈的制备方法 |
| CN115974804A (zh) * | 2023-02-03 | 2023-04-18 | 内蒙古莱科作物保护有限公司 | 一种新型芳基吡咯类化合物杀虫剂的合成工艺 |
| CN116589394A (zh) * | 2023-05-19 | 2023-08-15 | 开封博凯生物化工有限公司 | 以脯氨酸为缚酸剂生产溴虫腈的工艺 |
| CN118772034A (zh) * | 2024-09-12 | 2024-10-15 | 山东亿嘉农化有限公司 | 一种2-对氯苯基-5-（三氟甲基）吡咯-3-腈的制备工艺 |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4929634A (en) * | 1987-10-23 | 1990-05-29 | American Cyanamid Company | Method of and bait compositions for controlling mollusks |
| US5030735A (en) | 1990-07-31 | 1991-07-09 | American Cyanamid Company | Process for the preparation of insecticidal, acaricidal and nematicidal 2-aryl-5-(trifluoromethyl) pyrrole compounds |
| IL98235A (en) * | 1990-07-31 | 1999-07-14 | American Cyanamid Co | Process for the preparation of insecticidal acaridical and nematicidal 2-aryl-5-(trifluoromethyl) pyrrole compounds and intermediates thereof |
| US5144041A (en) | 1990-12-26 | 1992-09-01 | American Cyanamid Company | Process for the preparation of 2-aryl-1-substituted-5-(trifluoromethyl) pyrrole compounds useful as insecticidal, acaricidal and nematocidal agents and as intermediates for the manufacture of said agents |
| US5118816A (en) | 1990-12-26 | 1992-06-02 | American Cyanamid Company | 2-aryl-5-(trifluoromethyl)-2-pyrroline compounds useful in the manufacture of insecticidal, nematocidal and acaricidal arylpyrroles |
| YU8592A (sh) * | 1991-08-28 | 1994-06-10 | Flumroc Ag. | Postupak i uređaj za izradu ploča od mineralnih vlakana primenjenih kao nosač zidnog premaza |
| US5359090A (en) * | 1993-12-29 | 1994-10-25 | American Cyanamid Company | Alkoxymethylation of pyrroles |
| US5453508A (en) | 1994-10-11 | 1995-09-26 | American Cyanamid Company | Manufacture of 4-aryl-2-perfluoroalkyl-3-oxazolin-5-one from arylglycine |
| US5446170A (en) | 1994-11-22 | 1995-08-29 | American Cyanamid Company | Process for the manufacture of insecticidal arylpyrroles via oxazole amine intermediates |
| CN1140713A (zh) * | 1995-07-17 | 1997-01-22 | 中国科学院上海有机化学研究所 | 三氟甲基吡咯类化合物的一步合成法 |
| DE19540358A1 (de) | 1995-10-30 | 1997-05-07 | Bayer Ag | Verbessertes Verfahren zur Herstellung von 2-Chloracrylnitril |
| CZ293077B6 (cs) | 1996-08-02 | 2004-02-18 | American Cyanamid Company | Stabilní arylpyrrolové částice, způsob jejich přípravy a kompozice tvořené suspenzním koncentrátem, obsahující tyto částice |
| IL128343A0 (en) * | 1998-02-09 | 2000-01-31 | American Cyanamid Co | Process for the preparation of 2-aryl-5-(perfluoroalkyl) pyrrole compounds from N-(arylmethylene)-1-chloro-1-(perfluoroalkyl) methylamine compounds |
| JP4485638B2 (ja) * | 1999-03-09 | 2010-06-23 | ワイス・ホールディングズ・コーポレイション | 塩化ｎ−［１−クロロ−１−（ペルフルオロアルキル）メチル］アリールイミドイル化合物からの２−アリール−５−（ペルフルオロアルキル）ピロール化合物の製造方法 |
| TW200724033A (en) | 2001-09-21 | 2007-07-01 | Du Pont | Anthranilamide arthropodicide treatment |
| CN104016899A (zh) * | 2014-05-16 | 2014-09-03 | 浙江师范大学 | 一种溴虫腈的合成方法 |
-
2018
- 2018-03-05 MX MX2019010998A patent/MX2019010998A/es unknown
- 2018-03-05 CN CN201880016385.7A patent/CN110382462A/zh active Pending
- 2018-03-05 US US16/492,119 patent/US11584716B2/en active Active
- 2018-03-05 JP JP2019549579A patent/JP7260480B2/ja active Active
- 2018-03-05 CA CA3053443A patent/CA3053443A1/en active Pending
- 2018-03-05 WO PCT/EP2018/055261 patent/WO2018166819A1/en not_active Ceased
- 2018-03-05 KR KR1020197026719A patent/KR102623135B1/ko active Active
- 2018-03-12 AR ARP180100571A patent/AR111269A1/es unknown
-
2019
- 2019-08-22 IL IL268864A patent/IL268864B/en unknown
-
2022
- 2022-11-11 JP JP2022181032A patent/JP2023025035A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| JP7260480B2 (ja) | 2023-04-18 |
| JP2020511458A (ja) | 2020-04-16 |
| IL268864B (en) | 2022-02-01 |
| JP2023025035A (ja) | 2023-02-21 |
| BR112019017538A2 (pt) | 2020-04-07 |
| WO2018166819A1 (en) | 2018-09-20 |
| KR102623135B1 (ko) | 2024-01-09 |
| US11584716B2 (en) | 2023-02-21 |
| CN110382462A (zh) | 2019-10-25 |
| US20210139422A1 (en) | 2021-05-13 |
| IL268864A (en) | 2019-10-31 |
| CA3053443A1 (en) | 2018-09-20 |
| MX2019010998A (es) | 2019-10-17 |
| KR20190128642A (ko) | 2019-11-18 |
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