ES2781780T3 - Procedimiento para la preparación de fluoruros de 5-fluoro-1H-pirazol-4-carbonitrilo - Google Patents
Procedimiento para la preparación de fluoruros de 5-fluoro-1H-pirazol-4-carbonitrilo Download PDFInfo
- Publication number
- ES2781780T3 ES2781780T3 ES16721748T ES16721748T ES2781780T3 ES 2781780 T3 ES2781780 T3 ES 2781780T3 ES 16721748 T ES16721748 T ES 16721748T ES 16721748 T ES16721748 T ES 16721748T ES 2781780 T3 ES2781780 T3 ES 2781780T3
- Authority
- ES
- Spain
- Prior art keywords
- chloride
- process according
- pyrazole
- carbonyl
- formula
- 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
- 238000000034 method Methods 0.000 title claims abstract description 24
- 238000002360 preparation method Methods 0.000 title claims abstract description 8
- -1 5-fluoro-1H-pyrazole-4-carbonitrile fluorides Chemical class 0.000 title claims description 14
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims abstract description 48
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims abstract description 28
- 239000002904 solvent Substances 0.000 claims abstract description 19
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 claims abstract description 18
- 239000000203 mixture Substances 0.000 claims abstract description 11
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims abstract description 10
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 claims abstract description 8
- SSWVFMSOKRXUJO-UHFFFAOYSA-N 5-chloro-1H-pyrazole-3-carbonyl chloride Chemical class ClC1=NNC(=C1)C(=O)Cl SSWVFMSOKRXUJO-UHFFFAOYSA-N 0.000 claims abstract description 8
- JFQHKAZLEJKYFD-UHFFFAOYSA-N 5-fluoro-1H-pyrazole-4-carbonyl fluoride Chemical class FC1=C(C=NN1)C(=O)F JFQHKAZLEJKYFD-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229940117389 dichlorobenzene Drugs 0.000 claims abstract description 8
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 claims abstract description 7
- 239000012025 fluorinating agent Substances 0.000 claims abstract description 6
- 239000003444 phase transfer catalyst Substances 0.000 claims description 17
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 14
- 239000011698 potassium fluoride Substances 0.000 claims description 13
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical compound CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 claims description 12
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical group [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 claims description 12
- WKHWMSFGRUVCNP-UHFFFAOYSA-M bis(dimethylamino)methylidene-dimethylazanium;chloride Chemical compound [Cl-].CN(C)C(N(C)C)=[N+](C)C WKHWMSFGRUVCNP-UHFFFAOYSA-M 0.000 claims description 8
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 235000003270 potassium fluoride Nutrition 0.000 claims description 6
- IPILPUZVTYHGIL-UHFFFAOYSA-M tributyl(methyl)azanium;chloride Chemical group [Cl-].CCCC[N+](C)(CCCC)CCCC IPILPUZVTYHGIL-UHFFFAOYSA-M 0.000 claims description 6
- IBWGNZVCJVLSHB-UHFFFAOYSA-M tetrabutylphosphanium;chloride Chemical compound [Cl-].CCCC[P+](CCCC)(CCCC)CCCC IBWGNZVCJVLSHB-UHFFFAOYSA-M 0.000 claims description 5
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- LYWKAJZTPLXHEM-UHFFFAOYSA-M bis(diethylamino)methylidene-diethylazanium;chloride Chemical compound [Cl-].CCN(CC)C(N(CC)CC)=[N+](CC)CC LYWKAJZTPLXHEM-UHFFFAOYSA-M 0.000 claims description 4
- CJTDRDJUGRBDKP-UHFFFAOYSA-N bis(dibutylamino)methylidene-dibutylazanium Chemical compound CCCCN(CCCC)C(N(CCCC)CCCC)=[N+](CCCC)CCCC CJTDRDJUGRBDKP-UHFFFAOYSA-N 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 2
- BRKFQVAOMSWFDU-UHFFFAOYSA-M tetraphenylphosphanium;bromide Chemical compound [Br-].C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 BRKFQVAOMSWFDU-UHFFFAOYSA-M 0.000 claims description 2
- 125000003944 tolyl group Chemical group 0.000 claims 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- BAPZCSMFCUVUHW-UHFFFAOYSA-N dichloro(fluoro)methane Chemical compound F[C](Cl)Cl BAPZCSMFCUVUHW-UHFFFAOYSA-N 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 25
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 16
- 150000001875 compounds Chemical class 0.000 description 13
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 239000003880 polar aprotic solvent Substances 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 8
- 229910052786 argon Inorganic materials 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 8
- 238000004821 distillation Methods 0.000 description 7
- CXMYJZYKGYORER-UHFFFAOYSA-N 3-(difluoromethyl)-5-fluoro-1-methylpyrazole-4-carbonyl fluoride Chemical compound CN1N=C(C(F)F)C(C(F)=O)=C1F CXMYJZYKGYORER-UHFFFAOYSA-N 0.000 description 6
- CHYVHFOEFHHBJB-UHFFFAOYSA-N 5-chloro-3-(difluoromethyl)-1-methylpyrazole-4-carbonyl chloride Chemical compound CN1N=C(C(F)F)C(C(Cl)=O)=C1Cl CHYVHFOEFHHBJB-UHFFFAOYSA-N 0.000 description 6
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 229910001515 alkali metal fluoride Inorganic materials 0.000 description 5
- 238000002955 isolation Methods 0.000 description 5
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical class O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 238000003682 fluorination reaction Methods 0.000 description 4
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- QDEGJIIFYAYGCK-UHFFFAOYSA-N 5-chloro-3-(difluoromethyl)-1-methylpyrazole-4-carbonyl fluoride Chemical compound CN1N=C(C(F)F)C(C(F)=O)=C1Cl QDEGJIIFYAYGCK-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical group 0.000 description 3
- 239000012454 non-polar solvent Substances 0.000 description 3
- 238000012216 screening Methods 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- OKIZCWYLBDKLSU-UHFFFAOYSA-M N,N,N-Trimethylmethanaminium chloride Chemical compound [Cl-].C[N+](C)(C)C OKIZCWYLBDKLSU-UHFFFAOYSA-M 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000000010 aprotic solvent Substances 0.000 description 2
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- USJRLGNYCQWLPF-UHFFFAOYSA-N chlorophosphane Chemical compound ClP USJRLGNYCQWLPF-UHFFFAOYSA-N 0.000 description 2
- 150000002222 fluorine compounds Chemical class 0.000 description 2
- SHFJWMWCIHQNCP-UHFFFAOYSA-M hydron;tetrabutylazanium;sulfate Chemical compound OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 2
- RKHXQBLJXBGEKF-UHFFFAOYSA-M tetrabutylphosphanium;bromide Chemical compound [Br-].CCCC[P+](CCCC)(CCCC)CCCC RKHXQBLJXBGEKF-UHFFFAOYSA-M 0.000 description 2
- PYVOHVLEZJMINC-UHFFFAOYSA-N trihexyl(tetradecyl)phosphanium Chemical compound CCCCCCCCCCCCCC[P+](CCCCCC)(CCCCCC)CCCCCC PYVOHVLEZJMINC-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- FHDQNOXQSTVAIC-UHFFFAOYSA-M 1-butyl-3-methylimidazol-3-ium;chloride Chemical compound [Cl-].CCCCN1C=C[N+](C)=C1 FHDQNOXQSTVAIC-UHFFFAOYSA-M 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- WIWMMJPXRWAZBB-UHFFFAOYSA-N 5-chloro-1,3-dimethylpyrazole-4-carbonyl chloride Chemical compound CC1=NN(C)C(Cl)=C1C(Cl)=O WIWMMJPXRWAZBB-UHFFFAOYSA-N 0.000 description 1
- FSLWXANTEMFPRQ-UHFFFAOYSA-N 5-fluoro-1,3-dimethylpyrazole-4-carbonyl fluoride Chemical compound CC1=NN(C)C(F)=C1C(F)=O FSLWXANTEMFPRQ-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- KXHPPCXNWTUNSB-UHFFFAOYSA-M benzyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1=CC=CC=C1 KXHPPCXNWTUNSB-UHFFFAOYSA-M 0.000 description 1
- FCPMOQKUPRKDAN-UHFFFAOYSA-N bis(dimethylamino)methylidene-dimethylazanium Chemical compound CN(C)C(N(C)C)=[N+](C)C FCPMOQKUPRKDAN-UHFFFAOYSA-N 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 125000005534 decanoate group Chemical class 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 150000005218 dimethyl ethers Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000002608 ionic liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- QVCQZMQFJMPZNT-UHFFFAOYSA-N n-bromo-n-ethylethanamine Chemical compound CCN(Br)CC QVCQZMQFJMPZNT-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- VBKNTGMWIPUCRF-UHFFFAOYSA-M potassium;fluoride;hydrofluoride Chemical compound F.[F-].[K+] VBKNTGMWIPUCRF-UHFFFAOYSA-M 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 150000004023 quaternary phosphonium compounds Chemical class 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- IHYBXORJAWUZPC-UHFFFAOYSA-M tetrakis(diethylamino)phosphanium;chloride Chemical compound [Cl-].CCN(CC)[P+](N(CC)CC)(N(CC)CC)N(CC)CC IHYBXORJAWUZPC-UHFFFAOYSA-M 0.000 description 1
- LBEHYYDULUBKAH-UHFFFAOYSA-M tetrakis(dimethylamino)phosphanium;chloride Chemical compound [Cl-].CN(C)[P+](N(C)C)(N(C)C)N(C)C LBEHYYDULUBKAH-UHFFFAOYSA-M 0.000 description 1
- WAGFXJQAIZNSEQ-UHFFFAOYSA-M tetraphenylphosphonium chloride Chemical compound [Cl-].C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 WAGFXJQAIZNSEQ-UHFFFAOYSA-M 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 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
- C07D231/16—Halogen atoms or nitro radicals
-
- 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
- A01N29/00—Biocides, pest repellants or attractants, or plant growth regulators containing halogenated hydrocarbons
- A01N29/04—Halogen directly attached to a carbocyclic ring system
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Zoology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (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)
- Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP15290112 | 2015-04-29 | ||
| PCT/EP2016/059462 WO2016174121A1 (en) | 2015-04-29 | 2016-04-28 | Method for preparing 5-fluoro-1h-pyrazole-4-carbonyl fluorides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2781780T3 true ES2781780T3 (es) | 2020-09-07 |
Family
ID=53189745
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES16721748T Active ES2781780T3 (es) | 2015-04-29 | 2016-04-28 | Procedimiento para la preparación de fluoruros de 5-fluoro-1H-pirazol-4-carbonitrilo |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US10125103B2 (cg-RX-API-DMAC7.html) |
| EP (1) | EP3288923B1 (cg-RX-API-DMAC7.html) |
| JP (1) | JP6691925B2 (cg-RX-API-DMAC7.html) |
| KR (1) | KR102585411B1 (cg-RX-API-DMAC7.html) |
| CN (1) | CN107531640B (cg-RX-API-DMAC7.html) |
| BR (1) | BR112017022808B1 (cg-RX-API-DMAC7.html) |
| DK (1) | DK3288923T3 (cg-RX-API-DMAC7.html) |
| ES (1) | ES2781780T3 (cg-RX-API-DMAC7.html) |
| IL (1) | IL255256B (cg-RX-API-DMAC7.html) |
| MX (1) | MX390887B (cg-RX-API-DMAC7.html) |
| TW (1) | TWI705055B (cg-RX-API-DMAC7.html) |
| WO (1) | WO2016174121A1 (cg-RX-API-DMAC7.html) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114621178B (zh) * | 2022-03-23 | 2023-10-13 | 内蒙古源宏精细化工有限公司 | 一种氟代碳酸乙烯酯的制备工艺 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19544800A1 (de) | 1995-12-01 | 1997-06-05 | Bayer Ag | Verfahren zur Herstellung von 1,3-Dimethyl-5-fluor-pyrazol-4-carboxaniliden |
| DE19942374A1 (de) * | 1998-11-30 | 2000-05-31 | Solvay Fluor & Derivate | Verfahren zur Herstellung von Säurefluoriden aus Säurechloriden |
| DE102005044451A1 (de) * | 2005-09-17 | 2007-03-22 | Bayer Cropscience Gmbh | Verfahren zum Herstellen von 5-Fluor-1,3-dialkyl-1H-pyrazol-4-carbonsäurefluoriden |
| DE102007002674A1 (de) | 2007-01-18 | 2008-07-24 | Bayer Cropscience Ag | Verfahren zum Herstellen von substituierten Pyrazolcarbonsäurechloriden |
| DE102009003025A1 (de) | 2009-05-12 | 2010-11-18 | Ball Packaging Europe Gmbh | Verfahren zum Befüllen von Lebenmittelbehältern |
| AR076839A1 (es) * | 2009-05-15 | 2011-07-13 | Bayer Cropscience Ag | Derivados fungicidas de pirazol carboxamidas |
| EP2325173A1 (de) | 2009-11-19 | 2011-05-25 | Bayer CropScience AG | Verfahren zum Herstellen von 5-Fluor-1-alkyl-3-fluoralkyl-1H-pyrazol-4-carbonsäurechloriden |
| DK2560961T3 (en) | 2010-04-23 | 2017-02-20 | Bayer Ip Gmbh | METHOD FOR PREPARING 5-FLUORO-1-ALKYL-3-FLUORALKYL-1H-PYRAZOL-4-CARBOXYLYRIC CHLORIDE AND FLUORIDES |
| US20130296383A1 (en) * | 2010-11-15 | 2013-11-07 | Bayer Intellectual Property Gmbh | Decahydro-1,4-methanonaphthalen carboxamides |
| WO2012065947A1 (en) * | 2010-11-15 | 2012-05-24 | Bayer Cropscience Ag | 5-halogenopyrazolecarboxamides |
-
2016
- 2016-04-27 TW TW105113149A patent/TWI705055B/zh active
- 2016-04-28 MX MX2017013632A patent/MX390887B/es unknown
- 2016-04-28 BR BR112017022808-4A patent/BR112017022808B1/pt active IP Right Grant
- 2016-04-28 CN CN201680024155.6A patent/CN107531640B/zh active Active
- 2016-04-28 ES ES16721748T patent/ES2781780T3/es active Active
- 2016-04-28 WO PCT/EP2016/059462 patent/WO2016174121A1/en not_active Ceased
- 2016-04-28 KR KR1020177034297A patent/KR102585411B1/ko active Active
- 2016-04-28 DK DK16721748.8T patent/DK3288923T3/da active
- 2016-04-28 JP JP2017556167A patent/JP6691925B2/ja active Active
- 2016-04-28 US US15/569,681 patent/US10125103B2/en active Active
- 2016-04-28 EP EP16721748.8A patent/EP3288923B1/en active Active
-
2017
- 2017-10-25 IL IL255256A patent/IL255256B/en active IP Right Grant
Also Published As
| Publication number | Publication date |
|---|---|
| MX2017013632A (es) | 2018-03-08 |
| CN107531640B (zh) | 2020-10-27 |
| TWI705055B (zh) | 2020-09-21 |
| US20180118690A1 (en) | 2018-05-03 |
| KR20170141764A (ko) | 2017-12-26 |
| IL255256B (en) | 2020-05-31 |
| CN107531640A (zh) | 2018-01-02 |
| IL255256A0 (en) | 2017-12-31 |
| MX390887B (es) | 2025-03-21 |
| US10125103B2 (en) | 2018-11-13 |
| BR112017022808A2 (pt) | 2018-07-17 |
| EP3288923B1 (en) | 2020-02-12 |
| EP3288923A1 (en) | 2018-03-07 |
| TW201704215A (zh) | 2017-02-01 |
| WO2016174121A1 (en) | 2016-11-03 |
| DK3288923T3 (da) | 2020-04-20 |
| KR102585411B1 (ko) | 2023-10-05 |
| JP2018514538A (ja) | 2018-06-07 |
| JP6691925B2 (ja) | 2020-05-13 |
| BR112017022808B1 (pt) | 2022-04-19 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| ES2616005T3 (es) | Procedimiento para la preparación de cloruros y fluoruros de ácido 5-fluoro-1-alquil-3-fluoroalquil-1H-pirazol-4-carboxílico | |
| CN101631767A (zh) | 使用二氯-氟-三氟甲基苯的混合物制备2,6-二氯-4-(三氟甲基)苯基肼的方法 | |
| CN103635451B (zh) | 用于制备七氟烷的方法 | |
| ES2781780T3 (es) | Procedimiento para la preparación de fluoruros de 5-fluoro-1H-pirazol-4-carbonitrilo | |
| US8044247B2 (en) | Process for the preparation of fluoromethyl 2,2,2-trifluoro-1-(trifluoromethyl) ethyl ether | |
| JP6550927B2 (ja) | ヨウ化アルキル化合物の製造方法 | |
| DK2900634T3 (en) | PROCEDURE FOR PREPARING SUBSTITUTED SUBSTITUTED PHENYL AND PYRIDYLPYRROLIDINES | |
| KR20080066746A (ko) | 비페닐 유도체의 제조 방법 | |
| JP4051641B2 (ja) | モノフロロハロゲノアルカンの製造方法 | |
| KR102687147B1 (ko) | 크라운 에테르 촉매를 이용하여 치환된 클로로아실알에 의한 피콜린아미드의 알킬화 | |
| JP2014208604A (ja) | 芳香族アシル化合物の製造方法 | |
| JP5885160B2 (ja) | 環状ウレタンの製造方法 | |
| US20070293708A1 (en) | Process for preparing 2-bromo-4,4'-dialkylbiphenyl | |
| WO2015064711A1 (ja) | メチレンジスルホニルクロライド化合物の製造方法 | |
| JP2009209162A (ja) | １−ブロモ−３−フルオロベンゼンの製造方法 | |
| WO2011111464A1 (ja) | ３，５－ジ－ｔｅｒｔ－ブチルハロゲノベンゼンの製造方法 | |
| KR20150109396A (ko) | 5-플루오로-1-메틸-3-디플루오로메틸-1h-피라졸-4-카브알데히드 제조 방법 |