DK2729444T3 - Fremgangsmåde til fremstilling af 2-amino-5-cyano-n,3-dimethylbenzamid - Google Patents
Fremgangsmåde til fremstilling af 2-amino-5-cyano-n,3-dimethylbenzamid Download PDFInfo
- Publication number
- DK2729444T3 DK2729444T3 DK12734907.4T DK12734907T DK2729444T3 DK 2729444 T3 DK2729444 T3 DK 2729444T3 DK 12734907 T DK12734907 T DK 12734907T DK 2729444 T3 DK2729444 T3 DK 2729444T3
- Authority
- DK
- Denmark
- Prior art keywords
- formula
- amino
- cyano
- compounds
- mmol
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/14—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof
- C07C227/16—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof by reactions not involving the amino or carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/14—Preparation of carboxylic acid nitriles by reaction of cyanides with halogen-containing compounds with replacement of halogen atoms by cyano groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/58—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Toxicology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Claims (7)
1. Fremgangsmáde til fremstilling af 2-amino-5-cyano-N,3-dimethylbenzamid med formel (I)
kendetegnet ved, at (Al) forbindelser med formel (VI)
hvor R1 stár for alkyl, cycloalkyl, alkoxyalkyl, arylalkyl, thioalkyl, alkylthioalkyl, alkylsulfonylalkyl, cyanoalkyl, nitroalkyl, haloalkyl eller aryl, omsaettes i vand med en blanding af HBr/IhCk til forbindelser med formel (IV)
hvor X stár for Br, og R1 har de ovenfor anf0rte betegnelser, (A2) disse forbindelser med formel (IV) omsasttes med kobber(I)-cyanid i N,N-dimethylformamid, N,N-dimethylacetamid, N-methylformanilid, N-methylpyrrolidon, hexamethylphosphorsyretriamid eller dimethylsulfoxid til 2-amino-5-cyano-3-methylbenzoesyreester med formel (II)
(A3) disse 2-amino-5-cyano-3-methylbenzoesyreestere med formel (II) omsasttes med MeNEh under anvendelse af i det mindste en base til 2-amino-5-cyano-N,3-dimethylbenzamid med formel (I); eller (Bl) forbindelser med formel (VII),
hvor A stár for alkylen, alkoxyalkylen, omsasttes i vand med en blanding af HBr/H202 til forbindelser med formel (V)
(B2) disse forbindelser med formel (V) omsasttes med kobber(I)-cyanid i N,N-dimethylformamid, N,N-dimethylacetamid, N- methylformanilid, N-methylpyrrolidon, hexamethylphosphorsyretriamid eller dimethylsulfoxid til 2-amino-5-cyano-3-methylbenzoesyrediester med formel (III)
hvor A stár for alkylen, alkoxyalkylen, (B3) disse forbindelser med formel (III) oms*ttes med MeNH2 under anvendelse af i det mindste en base til 2-amino-5-cyano-N,3-dimethylbenzamid med formel (I).
2. Fremgangsmáde if0lge krav 1, kendetegnet ved, at forbindelsen med formel (I) opnás ved hjaelp af omsaetning af 2-amino-5-cyano-3-methylbenzoesyreestere med formel (II).
3. Fremgangsmáde if0lge krav 1, kendetegnet ved, at forbindelsen med formel (I) opnás ved hjaelp af omsaetning af 2-amino-5-cyano-3-methylbenzoesyrediestere med formel (III).
4. Fremgangsmáde if0lge et af kravene 1, 2 eller 3, kendetegnet ved, at basen er udvalgt af gruppen bestáende af natriumamid, natriumhydrid, natriumhydroxid, natriumcyanid, kaliumcyanid, kaliumcarbonat, natriumcarbonat, caesiumcarbonat, natriummethylat og triethylamin.
5. Fremgangsmáde if0lge et af kravene 6 eller 7, kendetegnet ved, at der til 1 mol af forbindelsen med formel (IV) eller (V) anvendes 0,8 mol til 1,4 mol kobber(I)-cyanid.
6. Forbindelser med den almene formel (II),
hvor R1 stár for pentyl, hexyl eller 2-ethylhexyl.
7. Forbindelser med den almene formel (III),
hvor A stár for ethylen eller hexylen.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP11173323 | 2011-07-08 | ||
| US201161506263P | 2011-07-11 | 2011-07-11 | |
| PCT/EP2012/063167 WO2013007603A1 (de) | 2011-07-08 | 2012-07-05 | Verfahren zur herstellung von 2-amino-5-cyano-n,3-dimethylbenzamid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DK2729444T3 true DK2729444T3 (da) | 2017-12-04 |
Family
ID=47505536
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK12734907.4T DK2729444T3 (da) | 2011-07-08 | 2012-07-05 | Fremgangsmåde til fremstilling af 2-amino-5-cyano-n,3-dimethylbenzamid |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US9169198B2 (da) |
| EP (1) | EP2729444B1 (da) |
| JP (1) | JP5955954B2 (da) |
| KR (1) | KR101953407B1 (da) |
| CN (2) | CN103702978B (da) |
| BR (1) | BR112014000473B1 (da) |
| DK (1) | DK2729444T3 (da) |
| ES (1) | ES2648308T3 (da) |
| IL (1) | IL230159A0 (da) |
| MX (1) | MX369283B (da) |
| TW (1) | TWI585069B (da) |
| WO (1) | WO2013007603A1 (da) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106278927A (zh) * | 2016-08-10 | 2017-01-04 | 袁春华 | 一种2‑氨基‑4‑溴‑n,5‑二甲基苯甲酰胺的合成方法 |
| EP3927685A4 (en) * | 2019-02-22 | 2022-11-23 | PI Industries Ltd. | PROCESS FOR THE SYNTHESIS OF ANTHRANILIC DIAMIDE COMPOUNDS AND ASSOCIATED INTERMEDIATES |
| WO2024116197A1 (en) * | 2022-11-30 | 2024-06-06 | Natco Pharma Limited | An improved process for the preparation of intermediate of cyantraniliprole |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU694465B2 (en) * | 1993-12-27 | 1998-07-23 | Eisai Co. Ltd. | Anthranilic acid derivative |
| US20040229900A1 (en) * | 1999-06-16 | 2004-11-18 | Astrazeneca Ab | Bispidine compounds useful in the treatment of cardiac arrythmias |
| SE9902268D0 (sv) * | 1999-06-16 | 1999-06-16 | Astra Ab | Pharmaceutically active compounds |
| TWI363756B (en) * | 2004-12-07 | 2012-05-11 | Du Pont | Method for preparing n-phenylpyrazole-1-carboxamides |
| US8247625B2 (en) | 2006-07-07 | 2012-08-21 | E I Du Pont De Nemours And Company | Catalytic addition of hydrofluorocarbons to fluoroolefins |
| US20090270435A1 (en) | 2006-11-29 | 2009-10-29 | Jeffrey Wayne Corbett | Spiroketone Acetyl-CoA Carboxylase Inhibitors |
| TWI395728B (zh) | 2006-12-06 | 2013-05-11 | Du Pont | 製備２-胺基-５-氰基苯甲酸衍生物之方法 |
| 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 |
| TWI430980B (zh) | 2007-06-29 | 2014-03-21 | Du Pont | 製備２－胺基－5－氰基苯甲酸衍生物之方法 |
| TWI434839B (zh) * | 2007-11-08 | 2014-04-21 | 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 |
| 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 |
| WO2010149359A1 (en) | 2009-06-26 | 2010-12-29 | Lonza Ltd | Process and intermediates for the preparation of benzimidazolecarboxylic acids |
| EP2668153B1 (en) * | 2011-01-28 | 2015-03-04 | E.I. Du Pont De Nemours And Company | Method for preparing 2-aminobenzamide derivatives |
-
2012
- 2012-07-05 DK DK12734907.4T patent/DK2729444T3/da active
- 2012-07-05 CN CN201280033434.0A patent/CN103702978B/zh not_active Expired - Fee Related
- 2012-07-05 MX MX2014000317A patent/MX369283B/es active IP Right Grant
- 2012-07-05 JP JP2014517809A patent/JP5955954B2/ja active Active
- 2012-07-05 EP EP12734907.4A patent/EP2729444B1/de active Active
- 2012-07-05 US US14/131,114 patent/US9169198B2/en active Active
- 2012-07-05 CN CN201710662432.2A patent/CN107365263A/zh active Pending
- 2012-07-05 WO PCT/EP2012/063167 patent/WO2013007603A1/de active Application Filing
- 2012-07-05 BR BR112014000473A patent/BR112014000473B1/pt active IP Right Grant
- 2012-07-05 ES ES12734907.4T patent/ES2648308T3/es active Active
- 2012-07-05 KR KR1020147000103A patent/KR101953407B1/ko active IP Right Grant
- 2012-07-06 TW TW101124346A patent/TWI585069B/zh active
-
2013
- 2013-12-25 IL IL230159A patent/IL230159A0/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JP5955954B2 (ja) | 2016-07-20 |
| US20140148611A1 (en) | 2014-05-29 |
| TWI585069B (zh) | 2017-06-01 |
| WO2013007603A1 (de) | 2013-01-17 |
| CN107365263A (zh) | 2017-11-21 |
| JP2014527032A (ja) | 2014-10-09 |
| EP2729444B1 (de) | 2017-08-23 |
| MX2014000317A (es) | 2014-02-19 |
| TW201311618A (zh) | 2013-03-16 |
| CN103702978B (zh) | 2018-03-06 |
| ES2648308T3 (es) | 2017-12-29 |
| KR20140039256A (ko) | 2014-04-01 |
| BR112014000473A2 (pt) | 2017-02-21 |
| US9169198B2 (en) | 2015-10-27 |
| CN103702978A (zh) | 2014-04-02 |
| EP2729444A1 (de) | 2014-05-14 |
| BR112014000473B1 (pt) | 2020-04-14 |
| KR101953407B1 (ko) | 2019-02-28 |
| IL230159A0 (en) | 2014-03-06 |
| MX369283B (es) | 2019-11-04 |
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