TWI363050B - Preparation of 2-dihaloacyl-3-aminoacrylic esters and 3-dihalomethylpyrazole-4-carboxylic esters - Google Patents
Preparation of 2-dihaloacyl-3-aminoacrylic esters and 3-dihalomethylpyrazole-4-carboxylic esters Download PDFInfo
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- TWI363050B TWI363050B TW093132065A TW93132065A TWI363050B TW I363050 B TWI363050 B TW I363050B TW 093132065 A TW093132065 A TW 093132065A TW 93132065 A TW93132065 A TW 93132065A TW I363050 B TWI363050 B TW I363050B
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- Prior art keywords
- formula
- alkyl
- group
- independently
- alkyl group
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- 150000002148 esters Chemical class 0.000 title abstract description 5
- 238000002360 preparation method Methods 0.000 title description 10
- 239000002253 acid Substances 0.000 claims abstract description 16
- 150000004820 halides Chemical class 0.000 claims abstract description 6
- 239000003960 organic solvent Substances 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 37
- -1 dialkylamino acrylate Chemical compound 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 239000007789 gas Chemical group 0.000 claims description 17
- 229910052731 fluorine Inorganic materials 0.000 claims description 14
- 239000011737 fluorine Substances 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 125000001153 fluoro group Chemical group F* 0.000 claims description 12
- 239000000460 chlorine Chemical group 0.000 claims description 10
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 9
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 9
- 229910052794 bromium Inorganic materials 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
- 150000001454 anthracenes Chemical class 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 150000002429 hydrazines Chemical class 0.000 claims description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 239000000010 aprotic solvent Substances 0.000 claims description 3
- 150000003222 pyridines Chemical class 0.000 claims description 3
- YTLYLLTVENPWFT-UPHRSURJSA-N (Z)-3-aminoacrylic acid Chemical compound N\C=C/C(O)=O YTLYLLTVENPWFT-UPHRSURJSA-N 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 1
- 229920000858 Cyclodextrin Polymers 0.000 claims 1
- 125000001188 haloalkyl group Chemical group 0.000 claims 1
- WHMDPDGBKYUEMW-UHFFFAOYSA-N pyridine-2-thiol Chemical compound SC1=CC=CC=N1 WHMDPDGBKYUEMW-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 141
- 239000000243 solution Substances 0.000 description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 20
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 239000012071 phase Substances 0.000 description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 13
- 239000012074 organic phase Substances 0.000 description 13
- 239000008346 aqueous phase Substances 0.000 description 11
- 239000000203 mixture Substances 0.000 description 11
- 239000002585 base Substances 0.000 description 10
- 238000003756 stirring Methods 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 8
- 238000004821 distillation Methods 0.000 description 8
- 235000019000 fluorine Nutrition 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 6
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N argon Substances [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 5
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 5
- 230000001681 protective effect Effects 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 239000000052 vinegar Substances 0.000 description 5
- 235000021419 vinegar Nutrition 0.000 description 5
- 239000008096 xylene Substances 0.000 description 5
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 4
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 4
- 150000007942 carboxylates Chemical class 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- JXTHNDFMNIQAHM-UHFFFAOYSA-N dichloroacetic acid Chemical compound OC(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-N 0.000 description 4
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 3
- HDZGCSFEDULWCS-UHFFFAOYSA-N monomethylhydrazine Chemical compound CNN HDZGCSFEDULWCS-UHFFFAOYSA-N 0.000 description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 238000005191 phase separation Methods 0.000 description 3
- 238000006798 ring closing metathesis reaction Methods 0.000 description 3
- 238000010025 steaming Methods 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- HGUFODBRKLSHSI-UHFFFAOYSA-N 2,3,7,8-tetrachloro-dibenzo-p-dioxin Chemical compound O1C2=CC(Cl)=C(Cl)C=C2OC2=C1C=C(Cl)C(Cl)=C2 HGUFODBRKLSHSI-UHFFFAOYSA-N 0.000 description 2
- BWZVCCNYKMEVEX-UHFFFAOYSA-N 2,4,6-Trimethylpyridine Chemical compound CC1=CC(C)=NC(C)=C1 BWZVCCNYKMEVEX-UHFFFAOYSA-N 0.000 description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- 241000208125 Nicotiana Species 0.000 description 2
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 2
- 206010036790 Productive cough Diseases 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- 238000005874 Vilsmeier-Haack formylation reaction Methods 0.000 description 2
- WDJHALXBUFZDSR-UHFFFAOYSA-M acetoacetate Chemical compound CC(=O)CC([O-])=O WDJHALXBUFZDSR-UHFFFAOYSA-M 0.000 description 2
- WEVYAHXRMPXWCK-FIBGUPNXSA-N acetonitrile-d3 Chemical compound [2H]C([2H])([2H])C#N WEVYAHXRMPXWCK-FIBGUPNXSA-N 0.000 description 2
- 125000002723 alicyclic group Chemical group 0.000 description 2
- 150000004056 anthraquinones Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- UCMIRNVEIXFBKS-UHFFFAOYSA-N beta-alanine Chemical compound NCCC(O)=O UCMIRNVEIXFBKS-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229950005499 carbon tetrachloride Drugs 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- 229960005215 dichloroacetic acid Drugs 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 2
- XONPDZSGENTBNJ-UHFFFAOYSA-N molecular hydrogen;sodium Chemical compound [Na].[H][H] XONPDZSGENTBNJ-UHFFFAOYSA-N 0.000 description 2
- SXHTXRAFCIZQCI-UHFFFAOYSA-N n,2,2-trichloroacetamide Chemical compound ClNC(=O)C(Cl)Cl SXHTXRAFCIZQCI-UHFFFAOYSA-N 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- LXNHXLLTXMVWPM-UHFFFAOYSA-N pyridoxine Chemical class CC1=NC=C(CO)C(CO)=C1O LXNHXLLTXMVWPM-UHFFFAOYSA-N 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 210000003802 sputum Anatomy 0.000 description 2
- 208000024794 sputum Diseases 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 description 2
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- RJGUJPSNJFGFLK-UHFFFAOYSA-N 1,1-dichloroethane;hydrochloride Chemical compound Cl.CC(Cl)Cl RJGUJPSNJFGFLK-UHFFFAOYSA-N 0.000 description 1
- PUNXVEAWLAVABA-UHFFFAOYSA-N 1,2,3,4-tetrahydroanthracene;1,2,5,6-tetrahydroanthracene Chemical compound C1=CC=C2C=C(CCCC3)C3=CC2=C1.C1=CCCC2=C1C=C1CCC=CC1=C2 PUNXVEAWLAVABA-UHFFFAOYSA-N 0.000 description 1
- LHASLBSEALHFGO-ASZAQJJISA-N 1-[(4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-[[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]pyrimidine-2,4-dione Chemical compound C1[C@H](O)[C@@H](CO)OC1N1C(=O)NC(=O)C(CO[C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)=C1 LHASLBSEALHFGO-ASZAQJJISA-N 0.000 description 1
- UPPPWUOZCSMDTR-UHFFFAOYSA-N 1-methyl-pyrazole-4-carboxylic acid Chemical compound CN1C=C(C(O)=O)C=N1 UPPPWUOZCSMDTR-UHFFFAOYSA-N 0.000 description 1
- KOPFEFZSAMLEHK-UHFFFAOYSA-N 1h-pyrazole-5-carboxylic acid Chemical class OC(=O)C=1C=CNN=1 KOPFEFZSAMLEHK-UHFFFAOYSA-N 0.000 description 1
- CRLSHTZUJTXOEL-UHFFFAOYSA-N 2,2-difluoroacetyl fluoride Chemical compound FC(F)C(F)=O CRLSHTZUJTXOEL-UHFFFAOYSA-N 0.000 description 1
- RBTHHWTYEDYOBS-UHFFFAOYSA-N 2,2-difluoroethanimidamide Chemical compound NC(=N)C(F)F RBTHHWTYEDYOBS-UHFFFAOYSA-N 0.000 description 1
- ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical group CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 description 1
- DPBJAVGHACCNRL-UHFFFAOYSA-N 2-(dimethylamino)ethyl prop-2-enoate Chemical compound CN(C)CCOC(=O)C=C DPBJAVGHACCNRL-UHFFFAOYSA-N 0.000 description 1
- OIALIKXMLIAOSN-UHFFFAOYSA-N 2-Propylpyridine Chemical compound CCCC1=CC=CC=N1 OIALIKXMLIAOSN-UHFFFAOYSA-N 0.000 description 1
- ZWHANXMMZRUTAY-UHFFFAOYSA-N 2-chloroprop-2-enal Chemical compound ClC(=C)C=O ZWHANXMMZRUTAY-UHFFFAOYSA-N 0.000 description 1
- BFEBVWFQQQJEHX-UHFFFAOYSA-N 2-methylidene-3-oxopent-4-enoic acid Chemical class OC(=O)C(=C)C(=O)C=C BFEBVWFQQQJEHX-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- FSVOSOSRDBUQQF-UHFFFAOYSA-N 3-(dimethylamino)propyl 3-oxobutanoate Chemical compound CN(C)CCCOC(=O)CC(C)=O FSVOSOSRDBUQQF-UHFFFAOYSA-N 0.000 description 1
- FNHVVMJBCILJGA-UHFFFAOYSA-N 4-methyl-pyrazole-3-carboxylic acid Chemical compound CC=1C=NNC=1C(O)=O FNHVVMJBCILJGA-UHFFFAOYSA-N 0.000 description 1
- JAWZAONCXMJLFT-UHFFFAOYSA-N 4-propylpyridine Chemical compound CCCC1=CC=NC=C1 JAWZAONCXMJLFT-UHFFFAOYSA-N 0.000 description 1
- UYZSNVLEDLCWGU-UHFFFAOYSA-N 5-(dimethylazaniumyl)pentanoate Chemical compound CN(C)CCCCC(O)=O UYZSNVLEDLCWGU-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- PXXNTAGJWPJAGM-VCOUNFBDSA-N Decaline Chemical compound C=1([C@@H]2C3)C=C(OC)C(OC)=CC=1OC(C=C1)=CC=C1CCC(=O)O[C@H]3C[C@H]1N2CCCC1 PXXNTAGJWPJAGM-VCOUNFBDSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 241000255925 Diptera Species 0.000 description 1
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical group [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- 240000000513 Santalum album Species 0.000 description 1
- 235000008632 Santalum album Nutrition 0.000 description 1
- XBDYBAVJXHJMNQ-UHFFFAOYSA-N Tetrahydroanthracene Natural products C1=CC=C2C=C(CCCC3)C3=CC2=C1 XBDYBAVJXHJMNQ-UHFFFAOYSA-N 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- JPTQGBTXAMWSMU-UHFFFAOYSA-L [Na+].[Ar].C([O-])([O-])=O.[Na+] Chemical compound [Na+].[Ar].C([O-])([O-])=O.[Na+] JPTQGBTXAMWSMU-UHFFFAOYSA-L 0.000 description 1
- GGOAIKUPVAYXFM-UHFFFAOYSA-N [O-2].[K+].[Ar].[K+] Chemical compound [O-2].[K+].[Ar].[K+] GGOAIKUPVAYXFM-UHFFFAOYSA-N 0.000 description 1
- JHZICVAIDBTSOQ-UHFFFAOYSA-N [O-2].[Na+].[Ar].[Na+] Chemical compound [O-2].[Na+].[Ar].[Na+] JHZICVAIDBTSOQ-UHFFFAOYSA-N 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 229930013930 alkaloid Natural products 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- KVNRLNFWIYMESJ-UHFFFAOYSA-N butyronitrile Chemical compound CCCC#N KVNRLNFWIYMESJ-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 description 1
- 125000006001 difluoroethyl group Chemical group 0.000 description 1
- 125000006371 dihalo methyl group Chemical group 0.000 description 1
- HOSXICNCYBUYAW-UHFFFAOYSA-N dimethylamino prop-2-enoate Chemical compound CN(C)OC(=O)C=C HOSXICNCYBUYAW-UHFFFAOYSA-N 0.000 description 1
- 229930004069 diterpene Natural products 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- FXENDKJYJGPXLJ-UHFFFAOYSA-N ethane;ethene Chemical compound CC.C=C.C=C FXENDKJYJGPXLJ-UHFFFAOYSA-N 0.000 description 1
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- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical class OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000001087 glyceryl triacetate Substances 0.000 description 1
- 235000013773 glyceryl triacetate Nutrition 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 125000002349 hydroxyamino group Chemical group [H]ON([H])[*] 0.000 description 1
- 150000002475 indoles Chemical class 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- LRDFRRGEGBBSRN-UHFFFAOYSA-N isobutyronitrile Chemical compound CC(C)C#N LRDFRRGEGBBSRN-UHFFFAOYSA-N 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- MVPDNJQLPITPIX-SNAWJCMRSA-N methyl (e)-3-(dimethylamino)prop-2-enoate Chemical compound COC(=O)\C=C\N(C)C MVPDNJQLPITPIX-SNAWJCMRSA-N 0.000 description 1
- RVKMHVYLDHMJSJ-UHFFFAOYSA-N methylhydrazine;toluene Chemical compound CNN.CC1=CC=CC=C1 RVKMHVYLDHMJSJ-UHFFFAOYSA-N 0.000 description 1
- PQIOSYKVBBWRRI-UHFFFAOYSA-N methylphosphonyl difluoride Chemical group CP(F)(F)=O PQIOSYKVBBWRRI-UHFFFAOYSA-N 0.000 description 1
- VMGAPWLDMVPYIA-HIDZBRGKSA-N n'-amino-n-iminomethanimidamide Chemical compound N\N=C\N=N VMGAPWLDMVPYIA-HIDZBRGKSA-N 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- JIKUXBYRTXDNIY-UHFFFAOYSA-N n-methyl-n-phenylformamide Chemical compound O=CN(C)C1=CC=CC=C1 JIKUXBYRTXDNIY-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
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- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- DHGFMVMDBNLMKT-UHFFFAOYSA-N propyl 3-oxobutanoate Chemical compound CCCOC(=O)CC(C)=O DHGFMVMDBNLMKT-UHFFFAOYSA-N 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- 235000008160 pyridoxine Nutrition 0.000 description 1
- 239000011677 pyridoxine Substances 0.000 description 1
- 150000003227 pyridoxines Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/30—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and unsaturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/34—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
- C07C229/36—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton containing six-membered aromatic rings with at least one amino group and one carboxyl group bound to the same carbon atom of the carbon skeleton
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10349500A DE10349500A1 (de) | 2003-10-23 | 2003-10-23 | Verfahren zum Herstellen von 2-Dihalogenacyl-3-amino-acrylsäureestern und 3-Dihalogenmethyl-pyrazol-4-carbonsäureestern |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW200526550A TW200526550A (en) | 2005-08-16 |
| TWI363050B true TWI363050B (en) | 2012-05-01 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW093132065A TWI363050B (en) | 2003-10-23 | 2004-10-22 | Preparation of 2-dihaloacyl-3-aminoacrylic esters and 3-dihalomethylpyrazole-4-carboxylic esters |
Country Status (14)
| Country | Link |
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| EP (1) | EP1678119B1 (enExample) |
| JP (1) | JP4725977B2 (enExample) |
| KR (1) | KR101116686B1 (enExample) |
| CN (1) | CN100422141C (enExample) |
| AT (1) | ATE494274T1 (enExample) |
| BR (1) | BRPI0415855B1 (enExample) |
| DE (2) | DE10349500A1 (enExample) |
| DK (1) | DK1678119T3 (enExample) |
| IL (1) | IL175024A (enExample) |
| IN (1) | IN2006DE01793A (enExample) |
| MX (1) | MXPA06004339A (enExample) |
| TW (1) | TWI363050B (enExample) |
| WO (1) | WO2005042468A1 (enExample) |
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| ES2427634T3 (es) | 2003-08-28 | 2013-10-31 | Universal Can Corporation | Equipo de fabricación de botellas |
| DE10352082A1 (de) * | 2003-10-23 | 2005-05-25 | Bayer Cropscience Ag | Hexylcarboxanilide |
| DE102006039909A1 (de) * | 2006-08-25 | 2008-03-13 | Bayer Cropscience Ag | Verfahren zum Herstellen von 3-Dihalomethyl-pyrazol-4-carbonsäurederivaten |
| MX2009007029A (es) * | 2006-12-28 | 2009-11-09 | Mitsui Chemicals Agro Inc | Derivado de acil-3-aminoacrilonitrilo 2-fluorado y metodo para producir el mismo. |
| CA2687176C (en) * | 2007-05-31 | 2015-06-30 | Syngenta Limited | Process for the production of pyrazoles |
| EP1997808A1 (en) * | 2007-05-31 | 2008-12-03 | Syngeta Participations AG | Process for the production of pyrazoles |
| UA99460C2 (ru) | 2007-06-01 | 2012-08-27 | Басф Се | Способ получения n-замещенных (3-дигалометил-1-метилпиразол-4-ил)карбоксамидов |
| BRPI0812958A2 (pt) * | 2007-06-15 | 2014-12-09 | Basf Se | Processo para preparar compostos, uso de compostos, e, compostos |
| EP2008996A1 (en) * | 2007-06-27 | 2008-12-31 | Syngeta Participations AG | Process for the production of pyrazoles |
| EP2042482A1 (de) * | 2007-09-26 | 2009-04-01 | Bayer CropScience AG | Verfahren zur Herstellung von 2-Dihalogenacyl-3-amino-acrylsäure-Derivaten |
| EP2072497A1 (de) | 2007-12-21 | 2009-06-24 | Bayer CropScience AG | Verfahren zum Herstellen von 2-Fluoracyl-3-amino-acrylsäure-Derivaten |
| EP2133341A1 (de) * | 2008-02-25 | 2009-12-16 | Bayer CropScience AG | Verfahren zur regioselektiven Synthese von 1-Alkyl-3-haloalkyl-pyrazol-4-carbonsäure-Derivaten |
| EP2100883A1 (de) | 2008-03-10 | 2009-09-16 | Bayer CropScience AG | Verfahren zur regioselektiven Synthese von 1-Alkyl-3-haloalkyl-pyrazol-4carbonsäure-Derivaten |
| US8344156B2 (en) | 2008-03-18 | 2013-01-01 | Mitsui Chemicals Agro, Inc. | Method for producing fluorine-containing acylacetic acid derivative, method for producing fluorine-containing pyrazolecarboxylic acid ester derivative, and method for producing fluorine-containing pyrazolecarboxylic acid derivative |
| JP2009227643A (ja) * | 2008-03-25 | 2009-10-08 | Mitsui Chemicals Agro Inc | 含フッ素アルキルカルボン酸誘導体を利用した含フッ素ピラゾール誘導体の製造方法 |
| CN102015653B (zh) * | 2008-05-02 | 2013-09-11 | 巴斯夫欧洲公司 | 制备卤素取代的2-(氨基亚甲基)-3-氧代丁酸酯的方法 |
| WO2009133178A1 (de) * | 2008-05-02 | 2009-11-05 | Basf Se | Verfahren zur herstellung von 2-(aminomethyliden)-4,4-difluor-3-oxobuttersäureestern |
| ES2525807T3 (es) * | 2008-05-05 | 2014-12-30 | Basf Se | Procedimiento de preparación de compuestos de pirazol sustituidos en las posiciones 1, 3, 4 |
| US7601864B1 (en) * | 2008-05-08 | 2009-10-13 | Ufc Corporation | Method for synthesizing 4,4-dihalogen-2-(dialkylamino)methylene-3-oxy-alkylbutyrate and derivatives thereof |
| ATE555098T1 (de) | 2008-07-21 | 2012-05-15 | Basf Se | Verfahren zur herstellung 1,3-disubstituierter pyrazolcarbonsäureester |
| SG192550A1 (en) | 2008-07-25 | 2013-08-30 | Viiv Healthcare Co | Chemical compounds |
| JP5228817B2 (ja) * | 2008-11-12 | 2013-07-03 | セントラル硝子株式会社 | ピラゾール化合物の製造方法 |
| EP2376080B1 (en) | 2008-12-11 | 2017-09-13 | Shionogi&Co., Ltd. | Synthesis of carbamoylpyridone hiv integrase inhibitors and intermediates |
| EP2376453B1 (en) | 2008-12-11 | 2019-11-20 | VIIV Healthcare Company | Intermediates for carbamoylpyridone hiv integrase inhibitors |
| TWI518084B (zh) | 2009-03-26 | 2016-01-21 | 鹽野義製藥股份有限公司 | 哌喃酮與吡啶酮衍生物之製造方法 |
| AR077503A1 (es) * | 2009-07-28 | 2011-08-31 | Syngenta Participations Ag | Procesos relacionados con la alquilacion de pirazoles |
| CN102596911B (zh) | 2009-11-05 | 2015-04-08 | 巴斯夫欧洲公司 | 制备缩醛胺的方法及其在制备1,3-二取代的吡唑化合物中的用途 |
| BR112012010486A2 (pt) * | 2009-11-05 | 2016-03-15 | Basf Se | processo para preparação de compostos 1-3 pirazol, processo para preparação de um acido pirazolcarboxilico da formula ia e processo para preparação de um composto da formula v |
| TWI582097B (zh) | 2010-03-23 | 2017-05-11 | Ｖｉｉｖ醫療保健公司 | 製備胺甲醯吡啶酮衍生物及中間體之方法 |
| HUE031724T2 (en) * | 2010-08-10 | 2017-07-28 | Syngenta Participations Ag | Process for the preparation of 3-haloalkylpyrazole derivatives |
| JP5605104B2 (ja) * | 2010-09-10 | 2014-10-15 | セントラル硝子株式会社 | ピラゾール化合物の製造方法 |
| WO2012176717A1 (ja) * | 2011-06-22 | 2012-12-27 | セントラル硝子株式会社 | ピラゾール化合物の製造方法 |
| JP5915004B2 (ja) * | 2011-06-22 | 2016-05-11 | セントラル硝子株式会社 | ピラゾール化合物の製造方法 |
| JP5790195B2 (ja) * | 2011-06-22 | 2015-10-07 | セントラル硝子株式会社 | ピラゾール化合物の製造方法 |
| JP5793983B2 (ja) * | 2011-06-22 | 2015-10-14 | セントラル硝子株式会社 | ピラゾール化合物の製造方法 |
| JP5830957B2 (ja) * | 2011-06-22 | 2015-12-09 | セントラル硝子株式会社 | ピラゾール化合物の製造方法 |
| EP2623496A1 (de) * | 2012-02-01 | 2013-08-07 | Bayer CropScience AG | Verfahren zur Herstellung von 3,5-bis (fluoralkyl)-pyrazol-4-carbonsäure-Derivaten und 3,5-bis(fluoralkyl)-pyrazolen |
| CN102731402A (zh) * | 2012-06-29 | 2012-10-17 | 上海康鹏化学有限公司 | 3-三氟甲基吡唑-4-羧酸和3-二氟甲基吡唑-4-羧酸的制备方法 |
| US8871947B2 (en) | 2013-02-04 | 2014-10-28 | KingChem LLC | Preparation of alkyl 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid ester |
| US9765033B2 (en) | 2013-05-22 | 2017-09-19 | Bayer Cropscience Aktiengesellschaft | Method for the production of 3,5-bis(fluoroalkyl)pyrazole derivatives |
| US9512081B2 (en) | 2013-05-22 | 2016-12-06 | Bayer Cropscience Aktiengesellschaft | Process for preparing 3,5-bis(fluoroalkyl)pyrazole derivatives from α,α-dihaloamines |
| TWI647215B (zh) * | 2013-11-11 | 2019-01-11 | 德商拜耳作物科學股份有限公司 | 自α,α－二鹵胺製備３,５－雙鹵烷基吡唑衍生物之方法 |
| US9139507B2 (en) | 2013-12-09 | 2015-09-22 | KingChem LLC. | Process for the preparation of alkyl 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylate and its analogs |
| WO2015105129A1 (ja) | 2014-01-10 | 2015-07-16 | 旭硝子株式会社 | エーテル性酸素原子含有ペルフルオロアルキル基置換ピラゾール環化合物およびその製造方法 |
| CN106164049B (zh) * | 2014-03-24 | 2019-04-12 | 拜耳作物科学股份公司 | 由α,α-二卤胺和酮亚胺制备3,5-二(卤代烷基)吡唑衍生物的方法 |
| EP3015458A1 (en) | 2014-11-03 | 2016-05-04 | Bayer CropScience AG | Process for preparing 3,5-bis(haloalkyl)pyrazole derivatives from a,a-dihaloamines and ketimines |
| BR112016028702B1 (pt) | 2014-06-11 | 2021-05-04 | Bayer Cropscience Aktiengesellschaft | processo para preparação de derivados de 3,5-bis(haloalquil)pirazole via acilação de hidrazonas |
| DK3154947T3 (en) | 2014-06-11 | 2018-06-18 | Bayer Cropscience Ag | PROCEDURE FOR PREPARING 3,5-BIS (HALOGENAL COOL) PYRAZOLES BY ACYLATION OF KETIMINES |
| EP2987782A1 (en) | 2014-08-22 | 2016-02-24 | Solvay SA | Distillation process comprising at least two distillation steps to obtain purified halogenated carboxylic acid halide, and use of the purified halogenated carboxylic acid halide |
| CA2966702A1 (en) | 2014-11-17 | 2016-05-26 | Solvay Sa | Distillation process comprising at least two distillation steps to obtain purified halogenated carboxylic acid halide, and use of the purified halogenated carboxylic acid halide |
| CN104529899A (zh) * | 2014-12-19 | 2015-04-22 | 浙江泰达作物科技有限公司 | 高区域选择性制备1-烷基-3-卤代烷基吡唑衍生物的方法 |
| CN105541716B (zh) * | 2015-03-26 | 2024-02-23 | Ａｇｃ株式会社 | 吡唑衍生物的制造方法 |
| KR20160120009A (ko) | 2015-04-07 | 2016-10-17 | (주)부흥산업사 | 4,4-디플루오로-((2-디알킬아미노)메틸렌)-3-옥소부탄산 알킬에스테르의 새로운 제조방법 |
| EP3313820A1 (en) | 2015-06-26 | 2018-05-02 | Bayer CropScience Aktiengesellschaft | Process for preparing substituted pyrazoles containing haloalkoxy- and haloalkylthio groups from , -dihaloalkylamines and ketimines |
| EP3178813A1 (en) | 2015-12-09 | 2017-06-14 | Basf Se | Method for preparing halogenated 3-oxocarboxylates carrying a 2-alkoxymethylidene or a 2-dialkylaminomethylidene group |
| EP3455211A1 (en) * | 2016-05-10 | 2019-03-20 | Solvay SA | Composition comprising 3-(haloalkyl or formyl)-1h-pyrazole-4-carboxylic acids or esters, its manufacture and its use for the preparation of carboxamides |
| WO2018054807A1 (en) | 2016-09-21 | 2018-03-29 | Bayer Cropscience Aktiengesellschaft | Process for preparing 3-fluoroalkyl-5-pyrazolecarboxylates and 3-fluoroalkyl-5-pyrazolecarboxylic acids |
| JP2020532524A (ja) | 2017-09-04 | 2020-11-12 | ソルヴェイ（ソシエテ アノニム） | ジフルオロアセチルクロリドの製造方法及び製造中間体 |
| CN111116364B (zh) * | 2019-12-30 | 2022-11-11 | 浙江本立科技股份有限公司 | 2-多卤代乙酰基-3-烷氧基丙烯酸酯的制备方法 |
| CN113912541A (zh) * | 2021-10-29 | 2022-01-11 | 南通宝凯药业有限公司 | 一种3-二氟甲基-1-甲基-1h-吡唑-4-羧酸的制备方法 |
| CN114195715B (zh) * | 2021-12-31 | 2024-05-10 | 福建永晶科技股份有限公司 | 1-甲基-3-二氟甲基-4-吡唑酸和1-甲基-3-三氟甲基-4-吡唑酸的制备方法 |
| CN117447401B (zh) * | 2023-12-26 | 2024-04-19 | 山东国邦药业有限公司 | 一种二氟吡唑酸的合成方法 |
| CN120118034A (zh) * | 2025-05-14 | 2025-06-10 | 辽宁龙田化工科技有限公司 | 一种3-二氟甲基-1-甲基吡唑-4-羧酸的合成方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5093347A (en) * | 1991-01-28 | 1992-03-03 | Monsanto Company | 3-difluoromethylpyrazolecarboxamide fungicides, compositions and use |
| US5223526A (en) * | 1991-12-06 | 1993-06-29 | Monsanto Company | Pyrazole carboxanilide fungicides and use |
| US5498624A (en) * | 1995-05-03 | 1996-03-12 | Monsanto Company | Selected pyrazolyl derivatives |
| KR20000035081A (ko) * | 1998-11-10 | 2000-06-26 | 마크 에스. 아들러 | 2-(트리할로아세틸)-3-(치환된 아미노)-2-프로페노에이트 제조방법 |
| KR20010078067A (ko) * | 2000-01-28 | 2001-08-20 | 고사이 아끼오 | 디할로-화합물 및 비타민 ａ 유도체의 제조 방법 |
| DE10161978A1 (de) * | 2001-12-17 | 2003-06-26 | Bayer Ag | Verfahren zur Herstellung von 2-Halogenacyl-3-amino-acrylsäure-derivate |
-
2003
- 2003-10-23 DE DE10349500A patent/DE10349500A1/de not_active Withdrawn
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2004
- 2004-10-12 BR BRPI0415855-5B1A patent/BRPI0415855B1/pt not_active IP Right Cessation
- 2004-10-12 CN CNB2004800312031A patent/CN100422141C/zh not_active Expired - Lifetime
- 2004-10-12 MX MXPA06004339A patent/MXPA06004339A/es active IP Right Grant
- 2004-10-12 US US10/576,059 patent/US7358387B2/en not_active Expired - Lifetime
- 2004-10-12 JP JP2006535992A patent/JP4725977B2/ja not_active Expired - Lifetime
- 2004-10-12 DK DK04790277.0T patent/DK1678119T3/da active
- 2004-10-12 DE DE502004012095T patent/DE502004012095D1/de not_active Expired - Lifetime
- 2004-10-12 EP EP04790277A patent/EP1678119B1/de not_active Expired - Lifetime
- 2004-10-12 WO PCT/EP2004/011376 patent/WO2005042468A1/de not_active Ceased
- 2004-10-12 AT AT04790277T patent/ATE494274T1/de active
- 2004-10-12 KR KR1020067009068A patent/KR101116686B1/ko not_active Expired - Lifetime
- 2004-10-22 TW TW093132065A patent/TWI363050B/zh not_active IP Right Cessation
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| Publication number | Publication date |
|---|---|
| CN1871204A (zh) | 2006-11-29 |
| DK1678119T3 (da) | 2011-05-02 |
| BRPI0415855B1 (pt) | 2013-11-05 |
| KR101116686B1 (ko) | 2012-02-22 |
| EP1678119B1 (de) | 2011-01-05 |
| IN2006DE01793A (enExample) | 2007-08-10 |
| EP1678119A1 (de) | 2006-07-12 |
| WO2005042468A1 (de) | 2005-05-12 |
| BRPI0415855A (pt) | 2007-01-09 |
| US7358387B2 (en) | 2008-04-15 |
| US20060252944A1 (en) | 2006-11-09 |
| DE502004012095D1 (de) | 2011-02-17 |
| CN100422141C (zh) | 2008-10-01 |
| ATE494274T1 (de) | 2011-01-15 |
| MXPA06004339A (es) | 2006-06-05 |
| KR20060109901A (ko) | 2006-10-23 |
| IL175024A (en) | 2011-05-31 |
| DE10349500A1 (de) | 2005-06-02 |
| JP4725977B2 (ja) | 2011-07-13 |
| JP2007509850A (ja) | 2007-04-19 |
| TW200526550A (en) | 2005-08-16 |
| IL175024A0 (en) | 2006-08-20 |
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