ES2422297T3 - Proceso para la sulfinilación de un derivado de pirazol - Google Patents
Proceso para la sulfinilación de un derivado de pirazolInfo
- Publication number
- ES2422297T3 ES2422297T3 ES07822223T ES07822223T ES2422297T3 ES 2422297 T3 ES2422297 T3 ES 2422297T3 ES 07822223 T ES07822223 T ES 07822223T ES 07822223 T ES07822223 T ES 07822223T ES 2422297 T3 ES2422297 T3 ES 2422297T3
- Authority
- ES
- Spain
- Prior art keywords
- acid
- dimethylbenzenesulfonic
- sulfinylation
- cf3s
- amines
- 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.)
- Active
Links
- 150000003217 pyrazoles Chemical class 0.000 title abstract 2
- 239000002253 acid Substances 0.000 abstract 5
- 150000001412 amines Chemical class 0.000 abstract 3
- ZZXDRXVIRVJQBT-UHFFFAOYSA-N 2,3-dimethylbenzenesulfonic acid Chemical compound CC1=CC=CC(S(O)(=O)=O)=C1C ZZXDRXVIRVJQBT-UHFFFAOYSA-N 0.000 abstract 2
- QPZYPAMYHBOUTC-UHFFFAOYSA-N 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]pyrazole-3-carbonitrile Chemical compound NC1=CC(C#N)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl QPZYPAMYHBOUTC-UHFFFAOYSA-N 0.000 abstract 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 abstract 2
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- JIRHAGAOHOYLNO-UHFFFAOYSA-N (3-cyclopentyloxy-4-methoxyphenyl)methanol Chemical compound COC1=CC=C(CO)C=C1OC1CCCC1 JIRHAGAOHOYLNO-UHFFFAOYSA-N 0.000 abstract 1
- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 abstract 1
- CHZLVSBMXZSPNN-UHFFFAOYSA-N 2,4-dimethylbenzenesulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C(C)=C1 CHZLVSBMXZSPNN-UHFFFAOYSA-N 0.000 abstract 1
- IRLYGRLEBKCYPY-UHFFFAOYSA-N 2,5-dimethylbenzenesulfonic acid Chemical compound CC1=CC=C(C)C(S(O)(=O)=O)=C1 IRLYGRLEBKCYPY-UHFFFAOYSA-N 0.000 abstract 1
- BRETYAHLENMEAI-UHFFFAOYSA-N 2,6-dimethylbenzenesulfonic acid Chemical compound CC1=CC=CC(C)=C1S(O)(=O)=O BRETYAHLENMEAI-UHFFFAOYSA-N 0.000 abstract 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 abstract 1
- RJWBTWIBUIGANW-UHFFFAOYSA-N 4-chlorobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(Cl)C=C1 RJWBTWIBUIGANW-UHFFFAOYSA-N 0.000 abstract 1
- BRIXOPDYGQCZFO-UHFFFAOYSA-N 4-ethylphenylsulfonic acid Chemical compound CCC1=CC=C(S(O)(=O)=O)C=C1 BRIXOPDYGQCZFO-UHFFFAOYSA-N 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract 1
- -1 alkaline earth metal salt Chemical class 0.000 abstract 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 abstract 1
- 229940092714 benzenesulfonic acid Drugs 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 229910052731 fluorine Inorganic materials 0.000 abstract 1
- 239000011737 fluorine Substances 0.000 abstract 1
- 230000002140 halogenating effect Effects 0.000 abstract 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 abstract 1
- 229940071870 hydroiodic acid Drugs 0.000 abstract 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 abstract 1
- 229940098779 methanesulfonic acid Drugs 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 abstract 1
- KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/44—Oxygen and nitrogen or sulfur and nitrogen atoms
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Environmental Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Dentistry (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Tropical Medicine & Parasitology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Catalysts (AREA)
Abstract
Proceso para la sulfinilación de un derivado de pirazol, caracterizado porque el 5-amino-1-[2,6-dicloro-4-(trifluorometil) fenil]-1H-pirazol-3-carbonitrilo (II) se hace reaccionar con un agente de sulfinilación S en presencia deal menos un complejo de amina-ácido, en donde la amina o las aminas se seleccionan de aminas secundarias y/oterciarias y el o los ácidos se seleccionan de ácido clorhídrico, ácido fluorhídrico, ácido bromhídrico, ácidoyodhídrico, ácido p-toluenosulfónico, ácido bencenosulfónico, ácido 4-etilbencenosulfónico, ácido 4-clorobencenosulfónico, ácido xilenosulfónico, ácido 2,3-dimetilbencenosulfónico, ácido 2,4-dimetilbencenosulfónico,ácido 2,5-dimetilbencenosulfónico, ácido 2,6-dimetilbencenosulfónico, ácido 1-naftalenosulfónico, ácido 2-naftalenosulfónico, mezclas de dos o más de los isómeros del ácido dimetilbencenosulfónico, ácidomesitilenosulfónico, ácido metanosulfónico, ácido canforsulfónico, y ácido trifluorometilsulfónico, y con la adición deun agente de halogenación, en donde S es [CF3S(O)]2O; o CF3S(O)X en donde X significa flúor, cloro, bromo, yodo, un grupo hidroxi, o una sal de metal alcalino o alcalinotérreo del grupo hidroxi; omezclas de estos, en donde la temperatura de la mezcla de reacción en ningún momento exceda 39°C.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US86517806P | 2006-11-10 | 2006-11-10 | |
| US91364607P | 2007-04-24 | 2007-04-24 | |
| PCT/EP2007/061894 WO2008055880A1 (en) | 2006-11-10 | 2007-11-05 | Process for the sulfinylation of a pyrazole derivative |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2422297T3 true ES2422297T3 (es) | 2013-09-10 |
Family
ID=38983360
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES07822223T Active ES2422297T3 (es) | 2006-11-10 | 2007-11-05 | Proceso para la sulfinilación de un derivado de pirazol |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US20100004307A1 (es) |
| EP (1) | EP2084137B1 (es) |
| JP (1) | JP5450079B2 (es) |
| KR (1) | KR20090081421A (es) |
| AR (1) | AR063648A1 (es) |
| AU (1) | AU2007316721B2 (es) |
| BR (1) | BRPI0718758A2 (es) |
| CA (1) | CA2667565A1 (es) |
| DK (1) | DK2084137T3 (es) |
| EA (1) | EA016304B1 (es) |
| ES (1) | ES2422297T3 (es) |
| IL (1) | IL198261A0 (es) |
| MX (1) | MX2009004259A (es) |
| NZ (1) | NZ576638A (es) |
| PL (1) | PL2084137T3 (es) |
| WO (1) | WO2008055880A1 (es) |
| ZA (1) | ZA200903973B (es) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2630849C (en) | 2005-12-14 | 2013-05-14 | Makhteshim Chemical Works Ltd. | Polymorphs and amorphous forms of 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(trifluoromethyl)sulfinyl]-1h-pyrazole-3-carbonitrile |
| PL2081908T3 (pl) | 2006-11-10 | 2013-09-30 | Basf Agro B V Arnhem Nl Zuerich Branch | Sposób sulfinylowania pochodnej pirazolu |
| AU2007316720B2 (en) | 2006-11-10 | 2013-05-09 | Basf Se | Process for the sulfinylation of a pyrazole derivative |
| FR2925493B1 (fr) * | 2007-12-19 | 2011-09-30 | Vetoquinol | Procede de preparation du fipronil et d'analogues de celui-ci. |
| DK2349987T3 (da) | 2008-10-02 | 2013-03-11 | Basf Se | Fremgangsmåde til fremstilling og oprensning af trifluormethansulfinsyre |
| CN104926729B (zh) * | 2014-03-18 | 2018-01-19 | 上海泰禾国际贸易有限公司 | 一种合成氟虫腈的方法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2716453B1 (fr) * | 1994-02-22 | 1996-03-29 | Rhone Poulenc Agrochimie | Procédé de sulfinylation de composés hétérocycliques. |
| EP0165136B1 (fr) * | 1984-05-23 | 1989-03-01 | Rhone-Poulenc Chimie | Compositions détergentes comprenant des copolymères à base de polyoxyéthylène et de polyoxyalkylène utilisés comme agents antiredéposants , et leur procédé de preparation |
| GB8713768D0 (en) * | 1987-06-12 | 1987-07-15 | May & Baker Ltd | Compositions of matter |
| KR20000029759A (ko) * | 1996-08-01 | 2000-05-25 | 트롤리에 모리스;다니엘 델로스 | 치환디플루오로메틸기의그라프트화공정 |
| JPH11246555A (ja) * | 1997-10-31 | 1999-09-14 | Sumitomo Chem Co Ltd | フッ素置換ベンゾヘテロ環化合物 |
| JP2001220386A (ja) * | 1999-11-30 | 2001-08-14 | Takeda Chem Ind Ltd | オキサジアゾリン誘導体の製造方法 |
| JP2002020364A (ja) * | 2000-07-06 | 2002-01-23 | Konica Corp | スルフィン酸ナトリウム、スルフィン酸カリウムの製造方法およびそれらを用いた写真用カプラーの製造方法 |
| EP1331222A1 (en) * | 2002-01-28 | 2003-07-30 | Virbac S.A. | Environment friendly reagents and process for halogenoalkylsulfinylation of organic compounds |
| CN1176078C (zh) * | 2002-03-27 | 2004-11-17 | 江苏省农药研究所 | 带三氟甲基亚磺酰基的吡唑类化合物的亚磺酰化方法 |
| DK2349987T3 (da) * | 2008-10-02 | 2013-03-11 | Basf Se | Fremgangsmåde til fremstilling og oprensning af trifluormethansulfinsyre |
-
2007
- 2007-11-05 ES ES07822223T patent/ES2422297T3/es active Active
- 2007-11-05 MX MX2009004259A patent/MX2009004259A/es active IP Right Grant
- 2007-11-05 JP JP2009535704A patent/JP5450079B2/ja not_active Expired - Fee Related
- 2007-11-05 WO PCT/EP2007/061894 patent/WO2008055880A1/en not_active Ceased
- 2007-11-05 CA CA002667565A patent/CA2667565A1/en not_active Abandoned
- 2007-11-05 EA EA200900628A patent/EA016304B1/ru not_active IP Right Cessation
- 2007-11-05 DK DK07822223.9T patent/DK2084137T3/da active
- 2007-11-05 PL PL07822223T patent/PL2084137T3/pl unknown
- 2007-11-05 KR KR1020097011873A patent/KR20090081421A/ko not_active Ceased
- 2007-11-05 US US12/514,109 patent/US20100004307A1/en not_active Abandoned
- 2007-11-05 EP EP07822223.9A patent/EP2084137B1/en active Active
- 2007-11-05 BR BRPI0718758-0A patent/BRPI0718758A2/pt not_active Application Discontinuation
- 2007-11-05 NZ NZ576638A patent/NZ576638A/en not_active IP Right Cessation
- 2007-11-05 AU AU2007316721A patent/AU2007316721B2/en active Active
- 2007-11-09 AR ARP070105014A patent/AR063648A1/es not_active Application Discontinuation
-
2009
- 2009-04-21 IL IL198261A patent/IL198261A0/en unknown
- 2009-06-08 ZA ZA2009/03973A patent/ZA200903973B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| KR20090081421A (ko) | 2009-07-28 |
| EA016304B1 (ru) | 2012-04-30 |
| IL198261A0 (en) | 2009-12-24 |
| NZ576638A (en) | 2011-12-22 |
| EP2084137A1 (en) | 2009-08-05 |
| JP5450079B2 (ja) | 2014-03-26 |
| AR063648A1 (es) | 2009-02-04 |
| CA2667565A1 (en) | 2008-05-15 |
| BRPI0718758A2 (pt) | 2013-12-03 |
| JP2010509273A (ja) | 2010-03-25 |
| DK2084137T3 (da) | 2013-07-22 |
| AU2007316721A1 (en) | 2008-05-15 |
| PL2084137T3 (pl) | 2013-11-29 |
| ZA200903973B (en) | 2012-02-29 |
| US20100004307A1 (en) | 2010-01-07 |
| EA200900628A1 (ru) | 2009-12-30 |
| EP2084137B1 (en) | 2013-04-24 |
| MX2009004259A (es) | 2009-05-05 |
| WO2008055880A1 (en) | 2008-05-15 |
| AU2007316721B2 (en) | 2013-05-09 |
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