JP2011507872A5 - - Google Patents
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- Publication number
- JP2011507872A5 JP2011507872A5 JP2010539729A JP2010539729A JP2011507872A5 JP 2011507872 A5 JP2011507872 A5 JP 2011507872A5 JP 2010539729 A JP2010539729 A JP 2010539729A JP 2010539729 A JP2010539729 A JP 2010539729A JP 2011507872 A5 JP2011507872 A5 JP 2011507872A5
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound
- reagent
- alkyl
- salt reagent
- 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
- 150000001875 compounds Chemical class 0.000 claims description 41
- 239000003153 chemical reaction reagent Substances 0.000 claims description 36
- 238000000034 method Methods 0.000 claims description 36
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 15
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 14
- 229910052751 metal Inorganic materials 0.000 claims description 14
- 239000002184 metal Substances 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 13
- VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical class [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 claims description 11
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 claims description 11
- 239000003960 organic solvent Substances 0.000 claims description 11
- FKNQCJSGGFJEIZ-UHFFFAOYSA-N 4-methylpyridine Chemical compound CC1=CC=NC=C1 FKNQCJSGGFJEIZ-UHFFFAOYSA-N 0.000 claims description 10
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 claims description 10
- GWHJZXXIDMPWGX-UHFFFAOYSA-N 1,2,4-trimethylbenzene Chemical compound CC1=CC=C(C)C(C)=C1 GWHJZXXIDMPWGX-UHFFFAOYSA-N 0.000 claims description 6
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 claims description 6
- NURQLCJSMXZBPC-UHFFFAOYSA-N 3,4-dimethylpyridine Chemical compound CC1=CC=NC=C1C NURQLCJSMXZBPC-UHFFFAOYSA-N 0.000 claims description 6
- HWWYDZCSSYKIAD-UHFFFAOYSA-N 3,5-dimethylpyridine Chemical compound CC1=CN=CC(C)=C1 HWWYDZCSSYKIAD-UHFFFAOYSA-N 0.000 claims description 6
- ITQTTZVARXURQS-UHFFFAOYSA-N 3-methylpyridine Chemical compound CC1=CC=CN=C1 ITQTTZVARXURQS-UHFFFAOYSA-N 0.000 claims description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 5
- 125000006450 cyclopropyl cyclopropyl group Chemical group 0.000 claims description 5
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 5
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 5
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 claims description 5
- 125000006431 methyl cyclopropyl group Chemical group 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- 239000008096 xylene Substances 0.000 claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- -1 alkali metal cyanide Chemical class 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 4
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- UOCPQZOXOQZEGV-UHFFFAOYSA-N 2-amino-5-cyano-n,3-dimethylbenzamide Chemical compound CNC(=O)C1=CC(C#N)=CC(C)=C1N UOCPQZOXOQZEGV-UHFFFAOYSA-N 0.000 claims description 2
- VJXRKZJMGVSXPX-UHFFFAOYSA-N 4-ethylpyridine Chemical compound CCC1=CC=NC=C1 VJXRKZJMGVSXPX-UHFFFAOYSA-N 0.000 claims description 2
- XQABVLBGNWBWIV-UHFFFAOYSA-N 4-methoxypyridine Chemical compound COC1=CC=NC=C1 XQABVLBGNWBWIV-UHFFFAOYSA-N 0.000 claims description 2
- QJWQYVJVCXMTJP-UHFFFAOYSA-N 4-pyridin-4-ylmorpholine Chemical compound C1COCCN1C1=CC=NC=C1 QJWQYVJVCXMTJP-UHFFFAOYSA-N 0.000 claims description 2
- RGUKYNXWOWSRET-UHFFFAOYSA-N 4-pyrrolidin-1-ylpyridine Chemical compound C1CCCN1C1=CC=NC=C1 RGUKYNXWOWSRET-UHFFFAOYSA-N 0.000 claims description 2
- YSHMQTRICHYLGF-UHFFFAOYSA-N 4-tert-butylpyridine Chemical compound CC(C)(C)C1=CC=NC=C1 YSHMQTRICHYLGF-UHFFFAOYSA-N 0.000 claims description 2
- 229910021595 Copper(I) iodide Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims description 2
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 claims description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 claims description 2
- UETZVSHORCDDTH-UHFFFAOYSA-N iron(2+);hexacyanide Chemical compound [Fe+2].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] UETZVSHORCDDTH-UHFFFAOYSA-N 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- ODKLEQPZOCJQMT-UHFFFAOYSA-N n,n-diethylpyridin-4-amine Chemical compound CCN(CC)C1=CC=NC=C1 ODKLEQPZOCJQMT-UHFFFAOYSA-N 0.000 claims description 2
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- AUHZEENZYGFFBQ-UHFFFAOYSA-N 1,3,5-trimethylbenzene Chemical compound CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 2
- 0 *c(cc(cc1*)C#N)c1N Chemical compound *c(cc(cc1*)C#N)c1N 0.000 description 1
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- AWDBHOZBRXWRKS-UHFFFAOYSA-N tetrapotassium;iron(6+);hexacyanide Chemical compound [K+].[K+].[K+].[K+].[Fe+6].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] AWDBHOZBRXWRKS-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US845807P | 2007-12-19 | 2007-12-19 | |
| US61/008,458 | 2007-12-19 | ||
| PCT/US2008/087151 WO2009085816A1 (en) | 2007-12-19 | 2008-12-17 | Process for preparing 2-amino-5-cyanobenzoic acid derivatives |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2011507872A JP2011507872A (ja) | 2011-03-10 |
| JP2011507872A5 true JP2011507872A5 (enExample) | 2012-02-02 |
| JP5398734B2 JP5398734B2 (ja) | 2014-01-29 |
Family
ID=40521896
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010539729A Active JP5398734B2 (ja) | 2007-12-19 | 2008-12-17 | ２−アミノ−５−シアノ安息香酸誘導体を調製するための方法 |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US8247570B2 (enExample) |
| EP (1) | EP2231592B1 (enExample) |
| JP (1) | JP5398734B2 (enExample) |
| KR (1) | KR101587296B1 (enExample) |
| CN (1) | CN101970397B (enExample) |
| AR (1) | AR069838A1 (enExample) |
| AU (1) | AU2008343227B2 (enExample) |
| BR (1) | BRPI0819568B1 (enExample) |
| CA (1) | CA2709952A1 (enExample) |
| CL (1) | CL2008003756A1 (enExample) |
| CO (1) | CO6300860A2 (enExample) |
| IL (1) | IL206390A (enExample) |
| RU (1) | RU2010129913A (enExample) |
| TW (1) | TWI432421B (enExample) |
| WO (1) | WO2009085816A1 (enExample) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8242140B2 (en) | 2007-08-03 | 2012-08-14 | Boehringer Ingelheim International Gmbh | Viral polymerase inhibitors |
| KR20100098534A (ko) | 2007-12-19 | 2010-09-07 | 베링거 인겔하임 인터내셔날 게엠베하 | 바이러스 폴리머라제 억제제 |
| TWI431000B (zh) | 2008-03-05 | 2014-03-21 | Du Pont | 製備２－胺基－５－氰基苯甲酸衍生物之方法 |
| TW201247631A (en) | 2011-04-28 | 2012-12-01 | Du Pont | Herbicidal pyrazinones |
| MX369283B (es) | 2011-07-08 | 2019-11-04 | Bayer Ip Gmbh | Preparacion de 2-amino-5-ciano-n, 3-dimetilbenzamida. |
| JP2014529587A (ja) | 2011-08-12 | 2014-11-13 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | Ｎ−チオ−アントラニルアミド化合物、及び殺有害生物剤としてのそれらの使用 |
| CN103827103A (zh) | 2011-08-12 | 2014-05-28 | 巴斯夫欧洲公司 | N-硫代邻氨基苯甲酰胺化合物及其作为农药的用途 |
| EP2742023A1 (en) | 2011-08-12 | 2014-06-18 | Basf Se | N-thio-anthranilamide compounds and their use as pesticides |
| CA2842858A1 (en) | 2011-08-12 | 2013-02-21 | Basf Se | N-thio-anthranilamide compounds and their use as pesticides |
| JP2015502966A (ja) | 2011-12-21 | 2015-01-29 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | Ｎ−チオ−アントラニルアミド化合物、及び殺有害生物剤としてのそれらの使用 |
| WO2013113789A1 (en) | 2012-02-02 | 2013-08-08 | Basf Se | N-thio-anthranilamide compounds and their use as pesticides |
| WO2013117601A1 (de) | 2012-02-07 | 2013-08-15 | Bayer Intellectual Property Gmbh | Verfahren zur herstellung von substituierten anthranilsäure-derivaten |
| CN104003976B (zh) * | 2014-05-07 | 2016-03-16 | 肇庆市真格生物科技有限公司 | 多取代吡啶基吡唑酰胺及其制备方法和用途 |
| TWI678354B (zh) | 2014-05-29 | 2019-12-01 | 新加坡商艾佛艾姆希農業新加坡有限公司 | 藉空氣氧化製備３-甲基-２-硝基苯甲酸之製程 |
| CN105461683B (zh) * | 2015-11-18 | 2019-01-15 | 江苏省农用激素工程技术研究中心有限公司 | 邻氨基苯甲酰胺化合物的制备方法 |
| WO2020117493A1 (en) * | 2018-12-03 | 2020-06-11 | Fmc Corporation | Method for preparing n-phenylpyrazole-1-carboxamides |
| WO2020170092A1 (en) | 2019-02-18 | 2020-08-27 | Pi Industries Ltd. | A process for preparing anthranilic diamides and intermediates thereof |
| CN113614063A (zh) | 2019-02-22 | 2021-11-05 | Pi工业有限公司 | 合成氨茴二酰胺化合物及其中间体的方法 |
| TW202222162A (zh) | 2020-09-26 | 2022-06-16 | 印度商皮埃企業有限公司 | 鄰胺苯甲酸／醯胺化合物及其中間體的合成方法 |
| US20240308988A1 (en) | 2021-08-05 | 2024-09-19 | Syngenta Crop Protection Ag | Method For Controlling Diamide Resistant Pests and Compounds Therefor |
| CN120379959A (zh) | 2022-08-16 | 2025-07-25 | 安道麦马克西姆有限公司 | 用于经由氨基-氰基-苯衍生物制备溴氰虫酰胺的方法 |
| WO2024116197A1 (en) * | 2022-11-30 | 2024-06-06 | Natco Pharma Limited | An improved process for the preparation of intermediate of cyantraniliprole |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20050032107A (ko) | 2002-08-02 | 2005-04-06 | 메사추세츠 인스티튜트 오브 테크놀로지 | 구리를 촉매로 한 탄소-헤테로원자 결합 및 탄소-탄소결합 형성방법 |
| RS53629B1 (sr) | 2003-01-28 | 2015-04-30 | E.I.Du Pont De Nemours And Company | Cijano antranilamidni insekticidi |
| MY140912A (en) * | 2004-07-26 | 2010-01-29 | Du Pont | Mixtures of anthranilamide invertebrate pest control agents |
| TWI363756B (en) * | 2004-12-07 | 2012-05-11 | Du Pont | Method for preparing n-phenylpyrazole-1-carboxamides |
| DE102006042439A1 (de) * | 2006-09-09 | 2008-03-27 | Saltigo Gmbh | Verfahren zur katalytischen Herstellung von aromatischen oder heteroaromatischen Nitrilen |
| TWI415827B (zh) | 2006-12-21 | 2013-11-21 | Du Pont | 製備２-胺基-５-氰基苯甲酸衍生物之方法 |
| TWI431000B (zh) | 2008-03-05 | 2014-03-21 | Du Pont | 製備２－胺基－５－氰基苯甲酸衍生物之方法 |
-
2008
- 2008-12-16 TW TW097149061A patent/TWI432421B/zh active
- 2008-12-17 CA CA2709952A patent/CA2709952A1/en not_active Abandoned
- 2008-12-17 JP JP2010539729A patent/JP5398734B2/ja active Active
- 2008-12-17 KR KR1020107015703A patent/KR101587296B1/ko active Active
- 2008-12-17 EP EP08868511.0A patent/EP2231592B1/en active Active
- 2008-12-17 CL CL2008003756A patent/CL2008003756A1/es unknown
- 2008-12-17 RU RU2010129913/04A patent/RU2010129913A/ru unknown
- 2008-12-17 US US12/809,072 patent/US8247570B2/en active Active
- 2008-12-17 WO PCT/US2008/087151 patent/WO2009085816A1/en not_active Ceased
- 2008-12-17 AU AU2008343227A patent/AU2008343227B2/en active Active
- 2008-12-17 CN CN200880126979.XA patent/CN101970397B/zh active Active
- 2008-12-17 BR BRPI0819568-4A patent/BRPI0819568B1/pt active IP Right Grant
- 2008-12-19 AR ARP080105556A patent/AR069838A1/es unknown
-
2010
- 2010-06-15 IL IL206390A patent/IL206390A/en active IP Right Grant
- 2010-06-18 CO CO10073860A patent/CO6300860A2/es not_active Application Discontinuation
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