BR112017022808B1 - Processo para preparação de fluoretos de 5-fluoro-1h-pirazol-4-carbonila - Google Patents
Processo para preparação de fluoretos de 5-fluoro-1h-pirazol-4-carbonila Download PDFInfo
- Publication number
- BR112017022808B1 BR112017022808B1 BR112017022808-4A BR112017022808A BR112017022808B1 BR 112017022808 B1 BR112017022808 B1 BR 112017022808B1 BR 112017022808 A BR112017022808 A BR 112017022808A BR 112017022808 B1 BR112017022808 B1 BR 112017022808B1
- Authority
- BR
- Brazil
- Prior art keywords
- chloride
- process according
- pyrazol
- carbonyl
- chlorobenzene
- Prior art date
Links
- JFQHKAZLEJKYFD-UHFFFAOYSA-N 5-fluoro-1H-pyrazole-4-carbonyl fluoride Chemical class FC1=C(C=NN1)C(=O)F JFQHKAZLEJKYFD-UHFFFAOYSA-N 0.000 title claims abstract description 8
- 238000004519 manufacturing process Methods 0.000 title claims 2
- 238000000034 method Methods 0.000 claims abstract description 25
- -1 5-FLUORO-1H-PYRAZOLE-4-CARBONYL Chemical class 0.000 claims abstract description 9
- PUIREZSBEHKZON-UHFFFAOYSA-N 5-chloro-1h-pyrazole-4-carbonyl chloride Chemical class ClC(=O)C=1C=NNC=1Cl PUIREZSBEHKZON-UHFFFAOYSA-N 0.000 claims abstract description 9
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 48
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 25
- 239000002904 solvent Substances 0.000 claims description 19
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 17
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 claims description 16
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical compound CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 claims description 16
- 239000003444 phase transfer catalyst Substances 0.000 claims description 14
- PJJJBBJSCAKJQF-UHFFFAOYSA-N guanidinium chloride Chemical compound [Cl-].NC(N)=[NH2+] PJJJBBJSCAKJQF-UHFFFAOYSA-N 0.000 claims description 13
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical group [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 claims description 12
- 239000011698 potassium fluoride Substances 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 10
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 claims description 9
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims description 8
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 claims description 7
- 229940117389 dichlorobenzene Drugs 0.000 claims description 7
- 239000012025 fluorinating agent Substances 0.000 claims description 6
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 claims description 6
- 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 description 6
- 235000003270 potassium fluoride Nutrition 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 6
- IPILPUZVTYHGIL-UHFFFAOYSA-M tributyl(methyl)azanium;chloride Chemical group [Cl-].CCCC[N+](C)(CCCC)CCCC IPILPUZVTYHGIL-UHFFFAOYSA-M 0.000 claims description 6
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- BAPZCSMFCUVUHW-UHFFFAOYSA-N dichloro(fluoro)methane Chemical compound F[C](Cl)Cl BAPZCSMFCUVUHW-UHFFFAOYSA-N 0.000 claims description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 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
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 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
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([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
- 150000001768 cations Chemical class 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 27
- 229910052736 halogen Inorganic materials 0.000 abstract description 6
- 150000002367 halogens Chemical group 0.000 abstract description 6
- 238000002360 preparation method Methods 0.000 abstract description 5
- 239000012454 non-polar solvent Substances 0.000 abstract description 4
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 description 14
- 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
- 239000012300 argon atmosphere Substances 0.000 description 8
- 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 7
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 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 5
- 229910001515 alkali metal fluoride Inorganic materials 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical class O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 5
- 238000001914 filtration Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 238000003682 fluorination reaction Methods 0.000 description 3
- 150000002222 fluorine compounds Chemical class 0.000 description 3
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- 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 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-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
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000000010 aprotic solvent Substances 0.000 description 2
- 238000005660 chlorination reaction Methods 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 2
- 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 2
- PYVOHVLEZJMINC-UHFFFAOYSA-N trihexyl(tetradecyl)phosphanium Chemical class CCCCCCCCCCCCCC[P+](CCCCCC)(CCCCCC)CCCCCC PYVOHVLEZJMINC-UHFFFAOYSA-N 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- NXNNLKRZGDBQBQ-UHFFFAOYSA-M (dihexylamino)-tris(dimethylamino)phosphanium;chloride Chemical compound [Cl-].CCCCCCN([P+](N(C)C)(N(C)C)N(C)C)CCCCCC NXNNLKRZGDBQBQ-UHFFFAOYSA-M 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 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
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 108010081348 HRT1 protein Hairy Proteins 0.000 description 1
- 102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 description 1
- OKIZCWYLBDKLSU-UHFFFAOYSA-M N,N,N-Trimethylmethanaminium chloride Chemical compound [Cl-].C[N+](C)(C)C OKIZCWYLBDKLSU-UHFFFAOYSA-M 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
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- SZKKRCSOSQAJDE-UHFFFAOYSA-N Schradan Chemical group CN(C)P(=O)(N(C)C)OP(=O)(N(C)C)N(C)C SZKKRCSOSQAJDE-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 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
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000002170 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
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000002608 ionic liquid Substances 0.000 description 1
- 229910001512 metal fluoride Inorganic materials 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium 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
- 239000007858 starting material Substances 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- RKHXQBLJXBGEKF-UHFFFAOYSA-M tetrabutylphosphanium;bromide Chemical compound [Br-].CCCC[P+](CCCC)(CCCC)CCCC RKHXQBLJXBGEKF-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
- JCQGIZYNVAZYOH-UHFFFAOYSA-M trihexyl(tetradecyl)phosphanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCC[P+](CCCCCC)(CCCCCC)CCCCCC JCQGIZYNVAZYOH-UHFFFAOYSA-M 0.000 description 1
- RNPVEYFHULDPHA-UHFFFAOYSA-M tris(diethylamino)-(dihexylamino)phosphanium;chloride Chemical compound [Cl-].CCCCCCN([P+](N(CC)CC)(N(CC)CC)N(CC)CC)CCCCCC RNPVEYFHULDPHA-UHFFFAOYSA-M 0.000 description 1
- RRFNOQILDDWIGI-UHFFFAOYSA-M tris(diethylamino)-(dimethylamino)phosphanium;bromide Chemical compound [Br-].CCN(CC)[P+](N(C)C)(N(CC)CC)N(CC)CC RRFNOQILDDWIGI-UHFFFAOYSA-M 0.000 description 1
- 230000035899 viability Effects 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- 239000008096 xylene 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
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (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 (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP15290112 | 2015-04-29 | ||
| EP15290112.0 | 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 (2)
| Publication Number | Publication Date |
|---|---|
| BR112017022808A2 BR112017022808A2 (pt) | 2018-07-17 |
| BR112017022808B1 true BR112017022808B1 (pt) | 2022-04-19 |
Family
ID=53189745
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BR112017022808-4A BR112017022808B1 (pt) | 2015-04-29 | 2016-04-28 | Processo para preparação de fluoretos de 5-fluoro-1h-pirazol-4-carbonila |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US10125103B2 (https=) |
| EP (1) | EP3288923B1 (https=) |
| JP (1) | JP6691925B2 (https=) |
| KR (1) | KR102585411B1 (https=) |
| CN (1) | CN107531640B (https=) |
| BR (1) | BR112017022808B1 (https=) |
| DK (1) | DK3288923T3 (https=) |
| ES (1) | ES2781780T3 (https=) |
| IL (1) | IL255256B (https=) |
| MX (1) | MX390887B (https=) |
| TW (1) | TWI705055B (https=) |
| WO (1) | WO2016174121A1 (https=) |
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 |
| ES2616005T3 (es) * | 2010-04-23 | 2017-06-09 | Bayer Intellectual Property Gmbh | Procedimiento para la preparación de cloruros y fluoruros de ácido 5-fluoro-1-alquil-3-fluoroalquil-1H-pirazol-4-carboxílico |
| 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 ES ES16721748T patent/ES2781780T3/es active Active
- 2016-04-28 WO PCT/EP2016/059462 patent/WO2016174121A1/en not_active Ceased
- 2016-04-28 JP JP2017556167A patent/JP6691925B2/ja active Active
- 2016-04-28 EP EP16721748.8A patent/EP3288923B1/en active Active
- 2016-04-28 KR KR1020177034297A patent/KR102585411B1/ko active Active
- 2016-04-28 US US15/569,681 patent/US10125103B2/en active Active
- 2016-04-28 CN CN201680024155.6A patent/CN107531640B/zh active 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 DK DK16721748.8T patent/DK3288923T3/da active
-
2017
- 2017-10-25 IL IL255256A patent/IL255256B/en active IP Right Grant
Also Published As
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|---|---|
| JP6691925B2 (ja) | 2020-05-13 |
| BR112017022808A2 (pt) | 2018-07-17 |
| EP3288923B1 (en) | 2020-02-12 |
| IL255256B (en) | 2020-05-31 |
| EP3288923A1 (en) | 2018-03-07 |
| JP2018514538A (ja) | 2018-06-07 |
| US10125103B2 (en) | 2018-11-13 |
| WO2016174121A1 (en) | 2016-11-03 |
| US20180118690A1 (en) | 2018-05-03 |
| ES2781780T3 (es) | 2020-09-07 |
| CN107531640B (zh) | 2020-10-27 |
| DK3288923T3 (da) | 2020-04-20 |
| IL255256A0 (en) | 2017-12-31 |
| TWI705055B (zh) | 2020-09-21 |
| MX390887B (es) | 2025-03-21 |
| KR20170141764A (ko) | 2017-12-26 |
| TW201704215A (zh) | 2017-02-01 |
| CN107531640A (zh) | 2018-01-02 |
| KR102585411B1 (ko) | 2023-10-05 |
| MX2017013632A (es) | 2018-03-08 |
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