JP2011513422A5 - - Google Patents
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- Publication number
- JP2011513422A5 JP2011513422A5 JP2010549849A JP2010549849A JP2011513422A5 JP 2011513422 A5 JP2011513422 A5 JP 2011513422A5 JP 2010549849 A JP2010549849 A JP 2010549849A JP 2010549849 A JP2010549849 A JP 2010549849A JP 2011513422 A5 JP2011513422 A5 JP 2011513422A5
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound
- imidazole
- reagent
- alkyl
- 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 47
- 238000000034 method Methods 0.000 claims description 37
- 239000003153 chemical reaction reagent Substances 0.000 claims description 31
- 239000000203 mixture Substances 0.000 claims description 19
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 13
- 229910052751 metal Inorganic materials 0.000 claims description 13
- 239000002184 metal Substances 0.000 claims description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
- VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical class [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 claims description 9
- 239000003960 organic solvent Substances 0.000 claims description 9
- GWHJZXXIDMPWGX-UHFFFAOYSA-N 1,2,4-trimethylbenzene Chemical compound CC1=CC=C(C)C(C)=C1 GWHJZXXIDMPWGX-UHFFFAOYSA-N 0.000 claims description 8
- AUHZEENZYGFFBQ-UHFFFAOYSA-N 1,3,5-trimethylbenzene Chemical compound CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 claims description 8
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 claims description 7
- MCMFEZDRQOJKMN-UHFFFAOYSA-N 1-butylimidazole Chemical compound CCCCN1C=CN=C1 MCMFEZDRQOJKMN-UHFFFAOYSA-N 0.000 claims description 6
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 claims description 6
- XLSZMDLNRCVEIJ-UHFFFAOYSA-N 4-methylimidazole Chemical compound CC1=CNC=N1 XLSZMDLNRCVEIJ-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 239000007787 solid Substances 0.000 claims description 6
- 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
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 125000006431 methyl cyclopropyl group Chemical group 0.000 claims description 5
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-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
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 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 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 239000008096 xylene Substances 0.000 claims description 4
- CHRPUSCNMSNSKL-UHFFFAOYSA-N 1,1'-hexane-1,6-diylbis(1h-imidazole) Chemical compound C1=CN=CN1CCCCCCN1C=CN=C1 CHRPUSCNMSNSKL-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 3
- 238000001816 cooling Methods 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 238000003756 stirring Methods 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- LGCPYQSYWVJQCJ-UHFFFAOYSA-N 1-(4-imidazol-1-ylbutyl)imidazole Chemical compound C1=CN=CN1CCCCN1C=CN=C1 LGCPYQSYWVJQCJ-UHFFFAOYSA-N 0.000 claims description 2
- CRVLLZCRVARGGG-UHFFFAOYSA-N 1-(5-imidazol-1-ylpentyl)imidazole Chemical compound C1=CN=CN1CCCCCN1C=CN=C1 CRVLLZCRVARGGG-UHFFFAOYSA-N 0.000 claims description 2
- IWDFHWZHHOSSGR-UHFFFAOYSA-N 1-ethylimidazole Chemical compound CCN1C=CN=C1 IWDFHWZHHOSSGR-UHFFFAOYSA-N 0.000 claims description 2
- KGWVFQAPOGAVRF-UHFFFAOYSA-N 1-hexylimidazole Chemical compound CCCCCCN1C=CN=C1 KGWVFQAPOGAVRF-UHFFFAOYSA-N 0.000 claims description 2
- UPYVYJSWGZMBOU-UHFFFAOYSA-N 1-pentylimidazole Chemical compound CCCCCN1C=CN=C1 UPYVYJSWGZMBOU-UHFFFAOYSA-N 0.000 claims description 2
- IYVYLVCVXXCYRI-UHFFFAOYSA-N 1-propylimidazole Chemical compound CCCN1C=CN=C1 IYVYLVCVXXCYRI-UHFFFAOYSA-N 0.000 claims description 2
- 229910021595 Copper(I) iodide Inorganic materials 0.000 claims description 2
- -1 alkali metal cyanide Chemical class 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 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
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-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
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 0 *c1cc(C#N)cc(*)c1N Chemical compound *c1cc(C#N)cc(*)c1N 0.000 description 1
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- LDQICAMJIICDLF-UHFFFAOYSA-N potassium;iron(2+);iron(3+);hexacyanide Chemical compound [K+].[Fe+2].[Fe+3].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] LDQICAMJIICDLF-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 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
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US6829708P | 2008-03-05 | 2008-03-05 | |
| US61/068,297 | 2008-03-05 | ||
| PCT/US2009/036012 WO2009111553A1 (en) | 2008-03-05 | 2009-03-04 | Process for preparing 2-amino-5-cyanobenzoic acid derivatives |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2011513422A JP2011513422A (ja) | 2011-04-28 |
| JP2011513422A5 true JP2011513422A5 (enExample) | 2012-04-12 |
| JP5480167B2 JP5480167B2 (ja) | 2014-04-23 |
Family
ID=40550214
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010549849A Active JP5480167B2 (ja) | 2008-03-05 | 2009-03-04 | ２−アミノ−５−シアノ安息香酸誘導体を製造するための方法 |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US8242279B2 (enExample) |
| EP (1) | EP2254858B1 (enExample) |
| JP (1) | JP5480167B2 (enExample) |
| KR (1) | KR101609891B1 (enExample) |
| CN (1) | CN101965329B (enExample) |
| AR (1) | AR070803A1 (enExample) |
| BR (1) | BRPI0906098B8 (enExample) |
| CA (1) | CA2714409A1 (enExample) |
| CL (1) | CL2009000503A1 (enExample) |
| CO (1) | CO6290753A2 (enExample) |
| HU (1) | HUE032406T2 (enExample) |
| IL (1) | IL207526A (enExample) |
| MX (1) | MX2010009583A (enExample) |
| MY (1) | MY150514A (enExample) |
| RU (1) | RU2495869C2 (enExample) |
| TW (1) | TWI431000B (enExample) |
| UA (1) | UA105173C2 (enExample) |
| WO (1) | WO2009111553A1 (enExample) |
| ZA (1) | ZA201005350B (enExample) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI432421B (zh) | 2007-12-19 | 2014-04-01 | Du Pont | 製備２－胺基－５－氰基苯甲酸衍生物之方法 |
| HUE025309T2 (en) * | 2011-01-28 | 2016-01-28 | Du Pont | Process for the preparation of 2-aminobenzamide derivatives |
| EP2729444B1 (de) * | 2011-07-08 | 2017-08-23 | Bayer Intellectual Property GmbH | Verfahren zur herstellung von 2-amino-5-cyano-n,3-dimethylbenzamid |
| US8921567B2 (en) | 2011-08-12 | 2014-12-30 | Basf Se | Process for preparing N-substituted 1H-pyrazole-5-carbonylchloride compounds |
| MX2014001038A (es) | 2011-08-12 | 2014-03-27 | Basf Se | Compuestos tipo anilina. |
| CN103889960A (zh) | 2011-08-18 | 2014-06-25 | 巴斯夫欧洲公司 | 用于防治无脊椎动物害虫的氨基甲酰基甲氧基-和氨基甲酰基甲硫基-及氨基甲酰基甲基氨基苯甲酰胺 |
| US9199975B2 (en) | 2011-09-30 | 2015-12-01 | Asana Biosciences, Llc | Biaryl imidazole derivatives for regulating CYP17 |
| AU2012342564A1 (en) | 2011-11-21 | 2014-06-12 | Basf Se | Process for preparing N-substituted 1H-pyrazole-5-carboxylate compounds and derivatives thereof |
| BR112014019487A2 (pt) | 2012-02-07 | 2020-10-27 | Bayer Intellectual Property Gmbh | processo para preparar derivados de ácidos antranílico substituídos |
| CN103060837B (zh) * | 2013-01-29 | 2015-12-23 | 哈尔滨理工大学 | 一种2-氨基-5-溴-n,3-二甲基苯甲酰胺的制备方法 |
| KR20150135485A (ko) | 2013-03-28 | 2015-12-02 | 바스프 에스이 | 술피민의 제조 방법 및 술피민의 ｎ-（２-아미노-벤조일）-술피민으로의 제자리 전환 |
| 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 |
| CN108484572A (zh) * | 2018-04-29 | 2018-09-04 | 江苏省农用激素工程技术研究中心有限公司 | 新型双酰胺类化合物及其制备方法和应用 |
| US12234217B2 (en) * | 2018-12-03 | 2025-02-25 | Fmc Corporation | Method for preparing N-phenylpyrazole-1-carboxamides |
| WO2023012081A1 (en) | 2021-08-05 | 2023-02-09 | Syngenta Crop Protection Ag | Method for controlling diamide resistant pests & compounds therefor |
| CN114621144A (zh) * | 2022-03-23 | 2022-06-14 | 南开大学 | 一类氰基取代的苯基吡唑酰胺衍生物及其制备方法和用途 |
| 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 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI312274B (en) * | 2001-08-13 | 2009-07-21 | Du Pont | Method for controlling particular insect pests by applying anthranilamide compounds |
| KR20050032107A (ko) | 2002-08-02 | 2005-04-06 | 메사추세츠 인스티튜트 오브 테크놀로지 | 구리를 촉매로 한 탄소-헤테로원자 결합 및 탄소-탄소결합 형성방법 |
| PT1599463E (pt) | 2003-01-28 | 2013-09-03 | Du Pont | Insecticidas à base de ciano-antranilamida |
| 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 |
| TWI432421B (zh) | 2007-12-19 | 2014-04-01 | Du Pont | 製備２－胺基－５－氰基苯甲酸衍生物之方法 |
-
2009
- 2009-02-25 TW TW098106032A patent/TWI431000B/zh active
- 2009-03-04 CL CL2009000503A patent/CL2009000503A1/es unknown
- 2009-03-04 CN CN200980106569.3A patent/CN101965329B/zh active Active
- 2009-03-04 KR KR1020107022122A patent/KR101609891B1/ko active Active
- 2009-03-04 EP EP09718451.9A patent/EP2254858B1/en active Active
- 2009-03-04 CA CA2714409A patent/CA2714409A1/en not_active Abandoned
- 2009-03-04 US US12/920,401 patent/US8242279B2/en active Active
- 2009-03-04 HU HUE09718451A patent/HUE032406T2/en unknown
- 2009-03-04 WO PCT/US2009/036012 patent/WO2009111553A1/en not_active Ceased
- 2009-03-04 BR BRPI0906098A patent/BRPI0906098B8/pt active IP Right Grant
- 2009-03-04 MY MYPI20103504 patent/MY150514A/en unknown
- 2009-03-04 RU RU2010140605/04A patent/RU2495869C2/ru active
- 2009-03-04 UA UAA201010673A patent/UA105173C2/uk unknown
- 2009-03-04 MX MX2010009583A patent/MX2010009583A/es active IP Right Grant
- 2009-03-04 JP JP2010549849A patent/JP5480167B2/ja active Active
- 2009-03-05 AR ARP090100791A patent/AR070803A1/es unknown
-
2010
- 2010-07-27 ZA ZA2010/05350A patent/ZA201005350B/en unknown
- 2010-08-10 IL IL207526A patent/IL207526A/en active IP Right Grant
- 2010-09-03 CO CO10109228A patent/CO6290753A2/es not_active Application Discontinuation
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