JP2019521165A5 - - Google Patents
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- JP2019521165A5 JP2019521165A5 JP2019502626A JP2019502626A JP2019521165A5 JP 2019521165 A5 JP2019521165 A5 JP 2019521165A5 JP 2019502626 A JP2019502626 A JP 2019502626A JP 2019502626 A JP2019502626 A JP 2019502626A JP 2019521165 A5 JP2019521165 A5 JP 2019521165A5
- Authority
- JP
- Japan
- Prior art keywords
- compound
- formula
- chloro
- base
- reacting
- 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.)
- Granted
Links
- 238000000034 method Methods 0.000 claims description 36
- 150000001875 compounds Chemical class 0.000 claims description 33
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 12
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 10
- 239000002585 base Substances 0.000 claims description 8
- 125000001153 fluoro group Chemical group F* 0.000 claims description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- -1 malononitrile anion Chemical class 0.000 claims description 6
- 229910052763 palladium Inorganic materials 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 5
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- CUONGYYJJVDODC-UHFFFAOYSA-N malononitrile Chemical compound N#CCC#N CUONGYYJJVDODC-UHFFFAOYSA-N 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- QORFOTVNIVMCMZ-UHFFFAOYSA-N 2-(4-chloro-2,6-dimethylphenyl)propanedinitrile Chemical compound ClC1=CC(=C(C(=C1)C)C(C#N)C#N)C QORFOTVNIVMCMZ-UHFFFAOYSA-N 0.000 claims description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
- 239000000010 aprotic solvent Substances 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
- 238000011065 in-situ storage Methods 0.000 claims description 2
- 239000003446 ligand Substances 0.000 claims description 2
- MUJIDPITZJWBSW-UHFFFAOYSA-N palladium(2+) Chemical compound [Pd+2] MUJIDPITZJWBSW-UHFFFAOYSA-N 0.000 claims description 2
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 239000008096 xylene Substances 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 238000010668 complexation reaction Methods 0.000 claims 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 239000000725 suspension Substances 0.000 description 2
- JGDXDPYHIIUBEM-UHFFFAOYSA-N 2-(4-chloro-2,6-dimethylphenyl)acetic acid Chemical compound CC1=CC(Cl)=CC(C)=C1CC(O)=O JGDXDPYHIIUBEM-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000009918 complex formation Effects 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP16180827.4 | 2016-07-22 | ||
| EP16180827 | 2016-07-22 | ||
| PCT/EP2017/068345 WO2018015489A1 (en) | 2016-07-22 | 2017-07-20 | Process for the preparation of phenylmalonic acid dinitriles |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2019521165A JP2019521165A (ja) | 2019-07-25 |
| JP2019521165A5 true JP2019521165A5 (enExample) | 2020-08-27 |
| JP7046050B2 JP7046050B2 (ja) | 2022-04-01 |
Family
ID=56507536
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019502626A Active JP7046050B2 (ja) | 2016-07-22 | 2017-07-20 | フェニルマロン酸ジニトリルの調製方法 |
Country Status (12)
| Country | Link |
|---|---|
| US (3) | US10759742B2 (enExample) |
| EP (1) | EP3487837B1 (enExample) |
| JP (1) | JP7046050B2 (enExample) |
| CN (1) | CN109476588A (enExample) |
| BR (1) | BR112019000963B1 (enExample) |
| DK (1) | DK3487837T3 (enExample) |
| ES (1) | ES2928635T3 (enExample) |
| HU (1) | HUE060023T2 (enExample) |
| IL (1) | IL263688B (enExample) |
| MX (1) | MX2019000753A (enExample) |
| WO (1) | WO2018015489A1 (enExample) |
| ZA (1) | ZA201900032B (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK3487837T3 (da) * | 2016-07-22 | 2022-10-31 | Syngenta Participations Ag | Fremgangsmåde til fremstilling af spiroheterocykliske pyrrolidindion-herbicider ved hjælp af mellemforbindelsen 2-(4-chlor-2,6-dimethylphenyl)eddikesyre |
| WO2018210616A1 (de) | 2017-05-15 | 2018-11-22 | Bayer Cropscience Aktiengesellschaft | Verfahren zur herstellung von (4-halogen-2,6-dialkylphenyl)malononitrilen |
| MX2020010636A (es) | 2018-04-10 | 2020-10-28 | Bayer Ag | Proceso para la produccion de acidos 2,6-dialquilfenilaceticos. |
| CN109096146B (zh) * | 2018-09-03 | 2020-11-10 | 杭州中美华东制药有限公司 | 阿那曲唑关键中间体的合成方法 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1997002243A1 (de) | 1995-06-30 | 1997-01-23 | Bayer Aktiengesellschaft | Dialkyl-halogenphenylsubstituierte ketoenole zur verwendung als herbizide und pestizide |
| TR200002366T2 (tr) * | 1998-03-13 | 2000-12-21 | Novartis Ag | Herbisit aktif 3-hidroksi-4-aril-5-oksopirazolin türevleri. |
| KR20020012274A (ko) * | 1999-06-16 | 2002-02-15 | 릴리 엠 씨즐러 스피허, 아네뜨 워너 | 제초제 제조용 중간체로서의 치환된 아릴말론산 디니트릴 |
| JPWO2002070477A1 (ja) * | 2001-03-01 | 2004-07-02 | 小野薬品工業株式会社 | ２−メチルインドール−４−酢酸、その製造方法およびその合成中間体の製造方法 |
| TWI313676B (en) | 2002-12-05 | 2009-08-21 | Syngenta Participations Ag | Process for the preparation of phenylmalonic acid dinitriles |
| DE102004053191A1 (de) * | 2004-11-04 | 2006-05-11 | Bayer Cropscience Ag | 2,6-Diethyl-4-methyl-phenyl substituierte Tetramsäure-Derivate |
| UA89218C2 (ru) | 2005-02-09 | 2010-01-11 | Сингента Партисипэйшнс Аг | Способ получения галогенбензолов (варианты) |
| GB0720126D0 (en) | 2007-10-15 | 2007-11-28 | Syngenta Participations Ag | Chemical compounds |
| US9067892B2 (en) * | 2008-12-12 | 2015-06-30 | Syngenta Crop Protection, Inc. | Spiroheterocyclic N-oxypiperidines as pesticides |
| WO2010102761A1 (de) | 2009-03-12 | 2010-09-16 | Bayer Cropscience Aktiengesellschaft | Verfahren zur herstellung von chlor- und bromaromaten |
| HUE039911T2 (hu) * | 2013-07-19 | 2019-02-28 | Syngenta Participations Ag | Új eljárás spiroheterociklusos pirrolidin-dionok elõállítására |
| DK3487837T3 (da) * | 2016-07-22 | 2022-10-31 | Syngenta Participations Ag | Fremgangsmåde til fremstilling af spiroheterocykliske pyrrolidindion-herbicider ved hjælp af mellemforbindelsen 2-(4-chlor-2,6-dimethylphenyl)eddikesyre |
-
2017
- 2017-07-20 DK DK17745158.0T patent/DK3487837T3/da active
- 2017-07-20 JP JP2019502626A patent/JP7046050B2/ja active Active
- 2017-07-20 CN CN201780044592.9A patent/CN109476588A/zh active Pending
- 2017-07-20 MX MX2019000753A patent/MX2019000753A/es unknown
- 2017-07-20 US US16/319,304 patent/US10759742B2/en active Active
- 2017-07-20 WO PCT/EP2017/068345 patent/WO2018015489A1/en not_active Ceased
- 2017-07-20 EP EP17745158.0A patent/EP3487837B1/en active Active
- 2017-07-20 HU HUE17745158A patent/HUE060023T2/hu unknown
- 2017-07-20 BR BR112019000963-9A patent/BR112019000963B1/pt active IP Right Grant
- 2017-07-20 ES ES17745158T patent/ES2928635T3/es active Active
-
2018
- 2018-12-13 IL IL263688A patent/IL263688B/en unknown
-
2019
- 2019-01-03 ZA ZA2019/00032A patent/ZA201900032B/en unknown
-
2020
- 2020-05-27 US US16/884,231 patent/US11136289B2/en active Active
-
2021
- 2021-06-03 US US17/337,615 patent/US20210284602A1/en not_active Abandoned
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