AR096111A2 - PROCEDURE FOR THE PREPARATION OF FLUORATED M-NITROBENZOIC ACID CHLORIDES - Google Patents
PROCEDURE FOR THE PREPARATION OF FLUORATED M-NITROBENZOIC ACID CHLORIDESInfo
- Publication number
- AR096111A2 AR096111A2 ARP140101736A ARP140101736A AR096111A2 AR 096111 A2 AR096111 A2 AR 096111A2 AR P140101736 A ARP140101736 A AR P140101736A AR P140101736 A ARP140101736 A AR P140101736A AR 096111 A2 AR096111 A2 AR 096111A2
- Authority
- AR
- Argentina
- Prior art keywords
- alkyl
- halogen
- variables
- formula
- fluorinated
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 3
- AFPHTEQTJZKQAQ-UHFFFAOYSA-N 3-nitrobenzoic acid Chemical compound OC(=O)C1=CC=CC([N+]([O-])=O)=C1 AFPHTEQTJZKQAQ-UHFFFAOYSA-N 0.000 title abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 title 1
- 229910052736 halogen Inorganic materials 0.000 abstract 5
- 150000002367 halogens Chemical class 0.000 abstract 4
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 3
- 238000006243 chemical reaction Methods 0.000 abstract 3
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 3
- 229910052731 fluorine Inorganic materials 0.000 abstract 3
- 239000011737 fluorine Substances 0.000 abstract 3
- 239000001257 hydrogen Substances 0.000 abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- 150000002431 hydrogen Chemical class 0.000 abstract 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 3
- NXTNASSYJUXJDV-UHFFFAOYSA-N 3-nitrobenzoyl chloride Chemical class [O-][N+](=O)C1=CC=CC(C(Cl)=O)=C1 NXTNASSYJUXJDV-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000004438 haloalkoxy group Chemical group 0.000 abstract 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- 230000002378 acidificating effect Effects 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 230000003197 catalytic effect Effects 0.000 abstract 1
- 239000012320 chlorinating reagent Substances 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- 125000001188 haloalkyl group Chemical group 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 150000003003 phosphines Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/02—Preparation of esters of nitric acid
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
- B01J31/0255—Phosphorus containing compounds
- B01J31/0257—Phosphorus acids or phosphorus acid esters
- B01J31/0262—Phosphorus acids or phosphorus acid esters comprising phosphinous acid (-ester) groups (R2P(OR')) or the isomeric phosphine oxide groups (R3P=O), i.e. R= C, R'= C, H
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
- B01J31/0255—Phosphorus containing compounds
- B01J31/0267—Phosphines or phosphonium compounds, i.e. phosphorus bonded to at least one carbon atom, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, the other atoms bonded to phosphorus being either carbon or hydrogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/34—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfuric acids
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/90—Catalytic systems characterized by the solvent or solvent system used
- B01J2531/96—Water
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/90—Catalytic systems characterized by the solvent or solvent system used
- B01J2531/98—Phase-transfer catalysis in a mixed solvent system containing at least 2 immiscible solvents or solvent phases
- B01J2531/985—Phase-transfer catalysis in a mixed solvent system containing at least 2 immiscible solvents or solvent phases in a water / organic solvent system
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0272—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing elements other than those covered by B01J31/0201 - B01J31/0255
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Reivindicación 1: Procedimiento para la preparación de cloruros de ácido m-nitrobenzoico fluorados de fórmula (1) en los que las variables tienen los siguientes significados: R¹, R², R³ y R⁴ hidrógeno, halógeno, ciano, nitro, alquilo C₁₋₆, halógenoalquilo C₁₋₆, alcoxi C₁₋₆ ó halógenoalcoxi C₁₋₆; en los que por lo menos uno de los restos R¹ a R⁴ significa flúor, mediante la reacción de ácidos m-nitrobenzoicos fluorados de fórmula (2), en los que las variables tienen los siguientes significados: R¹, R², R³, R⁴ hidrógeno, halógeno, ciano, nitro, alquilo C₁₋₆, halógenoalquilo C₁₋₆, alcoxi C₁₋₆ ó halógenoalcoxi C₁₋₆, en los que por lo menos uno de los restos R¹ a R⁴ significa flúor; con agentes clorantes, caracterizado porque la reacción se lleva a cabo en presencia de cantidades catalíticas de un derivado de fosfina de fórmula (3) en el que las variables tienen los siguientes significados: Rᵃ, Rᵇ, Rᶜ alquilo C₁₋₆ o fenilo que, dado el caso, puede estar sustituido por alquilo C₁₋₄; X oxígeno o dos átomos de cloro de enlace simple; n 0 ó 1. Reivindicación 8: Procedimiento para la preparación de cloruros de acido m-nitrobenzoico fluorados de fórmula (1) en los que las variables tienen los siguientes significados: R¹, R², R³ y R⁴ hidrógeno, halógeno, ciano, nitro, alquilo C₁₋₆, halógenoalquilo C₁₋₆, alcoxi C₁₋₆ ó halógenoalcoxi C₁₋₆; en los que por lo menos uno de los restos R¹ a R⁴ significa flúor, mediante la hidrólisis de m-nitrobenzotricloruros fluorados de fórmula (4) en la que las variables R¹, R², R³ y R⁴ tienen los significados nombrados anteriormente; caracterizado porque la reacción se lleva a cabo en presencia de un catalizador o en medio débilmente ácido, así como a temperaturas menores de 80ºC.Claim 1: Process for the preparation of fluorinated m-nitrobenzoic acid chlorides of formula (1) in which the variables have the following meanings: R¹, R², R³ and R⁴ hydrogen, halogen, cyano, nitro, C₁₋₆ alkyl, C₁₋₆ halogenalkyl, C₁₋₆alkoxy or halogenalkoxyCxi; in which at least one of the residues R¹ to R⁴ means fluorine, by the reaction of fluorinated m-nitrobenzoic acids of formula (2), in which the variables have the following meanings: R¹, R², R³, R⁴ hydrogen, halogen, cyano, nitro, C alquilo alkyl, halogen C₁₋₆ alkyl, C₁₋₆ alkoxy or C₁₋₆ halogen alkoxy, in which at least one of the residues R¹ to R⁴ means fluorine; with chlorinating agents, characterized in that the reaction is carried out in the presence of catalytic amounts of a phosphine derivative of formula (3) in which the variables have the following meanings: Rᵃ, Rᵇ, Rᶜ C₁₋₆ alkyl or phenyl which, if necessary, it may be substituted by C₁₋₄ alkyl; X oxygen or two single bond chlorine atoms; n 0 or 1. Claim 8: Process for the preparation of fluorinated m-nitrobenzoic acid chlorides of formula (1) in which the variables have the following meanings: R¹, R², R³ and R⁴ hydrogen, halogen, cyano, nitro, C₁₋₆ alkyl, halogen Cógeno alkyl, C₁₋₆ alkoxy or C₁₋₆ halogen alkoxy; in which at least one of the residues R¹ to R⁴ means fluorine, by hydrolysis of fluorinated m-nitrobenzotriclorides of formula (4) in which the variables R¹, R², R³ and R⁴ have the meanings mentioned above; characterized in that the reaction is carried out in the presence of a catalyst or in a weakly acidic medium, as well as at temperatures below 80 ° C.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE200510057681 DE102005057681A1 (en) | 2005-12-01 | 2005-12-01 | Preparation of fluorinated m-nitro-benzoic acid chloride compound, useful to prepare sulfonamide compound, comprises reacting a fluorinated m-nitro-benzoic acid compound with a chlorinating agent in the presence of a phosphine derivative |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR096111A2 true AR096111A2 (en) | 2015-12-09 |
Family
ID=38047613
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP140101737A AR096112A2 (en) | 2005-12-01 | 2014-04-25 | PROCEDURE FOR THE PREPARATION OF ANILINE DERIVATIVES |
| ARP140101736A AR096111A2 (en) | 2005-12-01 | 2014-04-25 | PROCEDURE FOR THE PREPARATION OF FLUORATED M-NITROBENZOIC ACID CHLORIDES |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP140101737A AR096112A2 (en) | 2005-12-01 | 2014-04-25 | PROCEDURE FOR THE PREPARATION OF ANILINE DERIVATIVES |
Country Status (5)
| Country | Link |
|---|---|
| CN (1) | CN101351443B (en) |
| AR (2) | AR096112A2 (en) |
| DE (1) | DE102005057681A1 (en) |
| UA (3) | UA96281C2 (en) |
| ZA (1) | ZA200805691B (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104610100B (en) * | 2015-01-09 | 2016-09-14 | 华东理工大学 | A nitrogen-chlorine type chlorination reagent |
| CN108218709A (en) * | 2016-12-14 | 2018-06-29 | 江苏联化科技有限公司 | The separation method of the fluoro- benzoic acid nitration products of the chloro- 4- of 2- |
| CN119504465B (en) * | 2023-08-16 | 2025-10-03 | 帕潘纳(北京)科技有限公司 | A preparation method of 3-amino-2-fluorobenzoyl halide |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5238908A (en) * | 1989-08-31 | 1993-08-24 | Rohm And Haas Company | Herbicidal glutaramic acids and derivatives |
| BR0315932A (en) * | 2002-10-30 | 2005-09-13 | Basf Ag | Process for the preparation of phenyl iso (thio) cyanates, compound, and process for the preparation thereof |
-
2005
- 2005-12-01 DE DE200510057681 patent/DE102005057681A1/en not_active Withdrawn
-
2006
- 2006-11-23 UA UAA200808447A patent/UA96281C2/en unknown
- 2006-11-23 CN CN2006800502073A patent/CN101351443B/en not_active Expired - Fee Related
- 2006-11-23 UA UAA201111380A patent/UA107567C2/en unknown
- 2006-11-23 UA UAA201101802A patent/UA98291C2/en unknown
-
2008
- 2008-06-30 ZA ZA200805691A patent/ZA200805691B/en unknown
-
2014
- 2014-04-25 AR ARP140101737A patent/AR096112A2/en not_active Application Discontinuation
- 2014-04-25 AR ARP140101736A patent/AR096111A2/en not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| ZA200805691B (en) | 2009-11-25 |
| UA107567C2 (en) | 2015-01-26 |
| AR096112A2 (en) | 2015-12-09 |
| CN101351443A (en) | 2009-01-21 |
| CN101351443B (en) | 2012-11-28 |
| UA96281C2 (en) | 2011-10-25 |
| DE102005057681A1 (en) | 2007-06-06 |
| UA98291C2 (en) | 2012-04-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FG | Grant, registration | ||
| FD | Application declared void or lapsed, e.g., due to non-payment of fee |