DK1682515T3 - PROCEDURE FOR PREPARING FLUORMETHYL-SUBSTITUTED HETEROCYCLES - Google Patents
PROCEDURE FOR PREPARING FLUORMETHYL-SUBSTITUTED HETEROCYCLES Download PDFInfo
- Publication number
- DK1682515T3 DK1682515T3 DK04765988.3T DK04765988T DK1682515T3 DK 1682515 T3 DK1682515 T3 DK 1682515T3 DK 04765988 T DK04765988 T DK 04765988T DK 1682515 T3 DK1682515 T3 DK 1682515T3
- Authority
- DK
- Denmark
- Prior art keywords
- alkyl
- formula
- process according
- chlorine
- substituted
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 19
- 125000000623 heterocyclic group Chemical class 0.000 claims description 29
- 229910052801 chlorine Chemical group 0.000 claims description 23
- 239000000460 chlorine Chemical group 0.000 claims description 22
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 20
- 229910052731 fluorine Inorganic materials 0.000 claims description 17
- 239000011737 fluorine Substances 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000003085 diluting agent Substances 0.000 claims description 8
- 239000012025 fluorinating agent Substances 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 239000007858 starting material Substances 0.000 claims description 6
- 239000003153 chemical reaction reagent Substances 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 5
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000004185 ester group Chemical group 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 150000002431 hydrogen Chemical group 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 14
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 9
- -1 R4 is Ci-C4-alkyl Chemical group 0.000 description 8
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 8
- 125000001246 bromo group Chemical group Br* 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 229910052736 halogen Inorganic materials 0.000 description 6
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
- 229910052794 bromium Inorganic materials 0.000 description 5
- 150000002367 halogens Chemical group 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 description 4
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 238000004293 19F NMR spectroscopy Methods 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 description 3
- GNFHJKJKZPONHS-UHFFFAOYSA-N ethyl 3-(dichloromethyl)-1-methylpyrazole-4-carboxylate Chemical compound CCOC(=O)C1=CN(C)N=C1C(Cl)Cl GNFHJKJKZPONHS-UHFFFAOYSA-N 0.000 description 3
- IKGLACJFEHSFNN-UHFFFAOYSA-N hydron;triethylazanium;trifluoride Chemical compound F.F.F.CCN(CC)CC IKGLACJFEHSFNN-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- BOSAWIQFTJIYIS-UHFFFAOYSA-N 1,1,1-trichloro-2,2,2-trifluoroethane Chemical compound FC(F)(F)C(Cl)(Cl)Cl BOSAWIQFTJIYIS-UHFFFAOYSA-N 0.000 description 2
- AJDIZQLSFPQPEY-UHFFFAOYSA-N 1,1,2-Trichlorotrifluoroethane Chemical compound FC(F)(Cl)C(F)(Cl)Cl AJDIZQLSFPQPEY-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- 101150041968 CDC13 gene Proteins 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 239000005864 Sulphur Substances 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-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
- 125000000217 alkyl group Chemical group 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 2
- 150000001733 carboxylic acid esters Chemical group 0.000 description 2
- AFYPFACVUDMOHA-UHFFFAOYSA-N chlorotrifluoromethane Chemical compound FC(F)(F)Cl AFYPFACVUDMOHA-UHFFFAOYSA-N 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- MRQQMVMIANXDKC-UHFFFAOYSA-N ethyl 3-(difluoromethyl)-1-methylpyrazole-4-carboxylate Chemical compound CCOC(=O)C1=CN(C)N=C1C(F)F MRQQMVMIANXDKC-UHFFFAOYSA-N 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 150000002391 heterocyclic compounds Chemical class 0.000 description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000011698 potassium fluoride Substances 0.000 description 2
- 235000003270 potassium fluoride Nutrition 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- GRJJQCWNZGRKAU-UHFFFAOYSA-N pyridin-1-ium;fluoride Chemical compound F.C1=CC=NC=C1 GRJJQCWNZGRKAU-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 125000006413 ring segment Chemical group 0.000 description 2
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 2
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 2
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 1
- PLCMVACJJSYDFV-UHFFFAOYSA-N 1,3-oxazole-2-carboxamide Chemical class NC(=O)C1=NC=CO1 PLCMVACJJSYDFV-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 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
- NGJQBGLVMZQTPD-UHFFFAOYSA-N 5-chloro-1h-pyrazole-4-carbaldehyde Chemical class ClC=1NN=CC=1C=O NGJQBGLVMZQTPD-UHFFFAOYSA-N 0.000 description 1
- 229910021583 Cobalt(III) fluoride Inorganic materials 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- WRQNANDWMGAFTP-UHFFFAOYSA-N Methylacetoacetic acid Chemical compound COC(=O)CC(C)=O WRQNANDWMGAFTP-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 229910001515 alkali metal fluoride Inorganic materials 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- LDDQLRUQCUTJBB-UHFFFAOYSA-N ammonium fluoride Chemical group [NH4+].[F-] LDDQLRUQCUTJBB-UHFFFAOYSA-N 0.000 description 1
- 125000002490 anilino group Chemical class [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- GUNJVIDCYZYFGV-UHFFFAOYSA-K antimony trifluoride Chemical class F[Sb](F)F GUNJVIDCYZYFGV-UHFFFAOYSA-K 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229950005499 carbon tetrachloride Drugs 0.000 description 1
- 150000003857 carboxamides Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000012320 chlorinating reagent Substances 0.000 description 1
- WZJQNLGQTOCWDS-UHFFFAOYSA-K cobalt(iii) fluoride Chemical compound F[Co](F)F WZJQNLGQTOCWDS-UHFFFAOYSA-K 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
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- KJEIIDJPPURRHQ-UHFFFAOYSA-N ethyl 3-[chloro(fluoro)methyl]-1-methylpyrazole-4-carboxylate Chemical compound CCOC(=O)C1=CN(C)N=C1C(F)Cl KJEIIDJPPURRHQ-UHFFFAOYSA-N 0.000 description 1
- DHVAVQNRJNZCEX-UHFFFAOYSA-N ethyl 4-(dichloromethyl)-1-methylpyrazole-3-carboxylate Chemical compound CCOC(=O)C1=NN(C)C=C1C(Cl)Cl DHVAVQNRJNZCEX-UHFFFAOYSA-N 0.000 description 1
- MJTBKFSXVZULSM-UHFFFAOYSA-N ethyl 4-(difluoromethyl)-1-methylpyrazole-3-carboxylate Chemical compound CCOC(=O)C1=NN(C)C=C1C(F)F MJTBKFSXVZULSM-UHFFFAOYSA-N 0.000 description 1
- 238000003682 fluorination reaction Methods 0.000 description 1
- 150000002222 fluorine compounds Chemical class 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 150000002429 hydrazines Chemical class 0.000 description 1
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- LNDHQUDDOUZKQV-UHFFFAOYSA-J molybdenum tetrafluoride Chemical compound F[Mo](F)(F)F LNDHQUDDOUZKQV-UHFFFAOYSA-J 0.000 description 1
- HDZGCSFEDULWCS-UHFFFAOYSA-N monomethylhydrazine Chemical compound CNN HDZGCSFEDULWCS-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000011775 sodium fluoride Substances 0.000 description 1
- 235000013024 sodium fluoride Nutrition 0.000 description 1
- HVZJRWJGKQPSFL-UHFFFAOYSA-N tert-Amyl methyl ether Chemical compound CCC(C)(C)OC HVZJRWJGKQPSFL-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 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 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D277/30—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10351088A DE10351088A1 (de) | 2003-10-31 | 2003-10-31 | Verfahren zum Herstellen von fluormethyl-substituierten Heterocyclen |
| PCT/EP2004/011809 WO2005044804A1 (de) | 2003-10-31 | 2004-10-19 | Verfahren zum herstellen von fluormethyl-substituierten heterocyclen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DK1682515T3 true DK1682515T3 (en) | 2014-11-17 |
Family
ID=34530016
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK04765988.3T DK1682515T3 (en) | 2003-10-31 | 2004-10-19 | PROCEDURE FOR PREPARING FLUORMETHYL-SUBSTITUTED HETEROCYCLES |
Country Status (14)
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| EP (1) | EP1682515B1 (enExample) |
| JP (1) | JP4936895B2 (enExample) |
| KR (1) | KR101123745B1 (enExample) |
| CN (1) | CN1875006B (enExample) |
| BR (1) | BRPI0416112A (enExample) |
| DE (1) | DE10351088A1 (enExample) |
| DK (1) | DK1682515T3 (enExample) |
| ES (1) | ES2524597T3 (enExample) |
| IL (1) | IL175148A (enExample) |
| IN (1) | IN2006DE01990A (enExample) |
| MX (1) | MXPA06004605A (enExample) |
| TW (1) | TWI359141B (enExample) |
| WO (1) | WO2005044804A1 (enExample) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| UA97498C2 (ru) | 2006-11-03 | 2012-02-27 | Басф Се | Способ получения дифторметилпиразолилкарбоксилатов |
| MX2009005863A (es) | 2006-12-21 | 2009-06-12 | Basf Se | Procedimiento para la preparacion de compuestos heterociclicos sustituidos por fluorometilo. |
| JP5456663B2 (ja) | 2007-06-01 | 2014-04-02 | ビーエーエスエフ ソシエタス・ヨーロピア | Ｎ−置換（３−ジハロメチル−１−メチル−ピラゾール−４−イル）カルボキサミドの製造方法 |
| AU2008263883B2 (en) * | 2007-06-15 | 2014-03-13 | Basf Se | Method for producing difluoromethyl-substituted pyrazole compounds |
| JP5340287B2 (ja) | 2007-08-16 | 2013-11-13 | ソルヴェイ（ソシエテ アノニム） | ４−フルオロ置換３−オキソ−アルカン酸のエステル類の調製方法 |
| AR072447A1 (es) | 2008-02-29 | 2010-09-01 | Basf Se | Proceso para preparar 2- alcoximetilen-4,4-difluoro-3-oxobutiratos de alquilo |
| BRPI0911898A2 (pt) | 2008-05-02 | 2015-10-13 | Basf Se | processo para preparar compostos, e, composto. |
| JP5602131B2 (ja) | 2008-05-02 | 2014-10-08 | ビーエーエスエフ ソシエタス・ヨーロピア | ハロゲン置換２−（アミノメチリデン）−３−オキソ酪酸エステルの製造方法 |
| US8598222B2 (en) | 2008-05-05 | 2013-12-03 | Basf Se | Method for preparing 1,3,4-substituted pyrazol compounds |
| KR20110004903A (ko) | 2008-05-08 | 2011-01-14 | 바스프 에스이 | 아릴카르복스아미드의 제조 방법 |
| EP2307384B1 (en) | 2008-07-21 | 2012-04-25 | Basf Se | Process for preparing 1,3-disubstituted pyrazolecarboxylic esters |
| US8981116B2 (en) | 2010-07-23 | 2015-03-17 | Solvay Sa | Process for the preparation of esters of 1-substituted-3-fluoroalkyl-pyrazole-4-carboxylic acids |
| FR2975990B1 (fr) * | 2011-06-01 | 2013-05-24 | Rhodia Operations | Procede de preparation d'un compose organique fluore |
| FR2975992B1 (fr) * | 2011-06-01 | 2013-11-08 | Rhodia Operations | Procede de preparation d'un compose fluoromethylpyrazole sous forme acide carboxylique ou derivee |
| BR112013032988A2 (pt) * | 2011-06-21 | 2016-08-16 | Bayer Ip Gmbh | método para a produção de pirazolilcarboxanilidas |
| WO2014124878A1 (en) * | 2013-02-15 | 2014-08-21 | Syngenta Participations Ag | Process for the preparation of bis-dihaloalkyl pyrazoles |
| EP3046908B1 (en) * | 2013-09-20 | 2017-08-16 | Bayer CropScience Aktiengesellschaft | Process for preparing 5-fluoro-1-alkyl-3-fluoroalkyl-1h-pyrazole-4-carbaldehyde |
| CN106045910B (zh) | 2016-08-15 | 2017-10-10 | 浙江永太科技股份有限公司 | 一种3‑(二氟甲基)‑1‑甲基‑1h‑吡唑‑4‑羧酸的合成方法 |
| CN115572210B (zh) * | 2022-12-08 | 2023-03-21 | 暨南大学 | 一种(1,2,2,2-四氟乙基)芳烃衍生物及其制备方法和应用 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6357568A (ja) * | 1982-04-16 | 1988-03-12 | ザ ダウ ケミカル カンパニ− | 液相ハロゲン交換反応における触媒再使用 |
| DE3400168A1 (de) * | 1984-01-04 | 1985-07-11 | Bayer Ag, 5090 Leverkusen | 5-halogenalkyl-1,3,4-thiadiazol-2-yloxyacetamide |
| DE3934924C2 (de) * | 1989-10-20 | 1994-01-27 | Huels Chemische Werke Ag | Verfahren zur Herstellung von 4-Alkoxycarbonyl-3-chlormethyl-2H-pyrazolen |
| US5126275A (en) * | 1990-09-19 | 1992-06-30 | Miles Inc. | Analytical method using tetrazolium salt indicators having a reflectance plateau |
| 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 |
| DE4231517A1 (de) * | 1992-09-21 | 1994-03-24 | Basf Ag | Carbonsäureanilide, Verfahren zu ihrer Herstellung und sie enthaltende Mittel zur Bekämpfung von Schadpilzen |
| DE19544800A1 (de) * | 1995-12-01 | 1997-06-05 | Bayer Ag | Verfahren zur Herstellung von 1,3-Dimethyl-5-fluor-pyrazol-4-carboxaniliden |
| DE19629828A1 (de) * | 1996-07-24 | 1998-01-29 | Bayer Ag | Carbanilide |
| JP3533134B2 (ja) * | 1999-02-15 | 2004-05-31 | 三井化学株式会社 | フッ素化剤及びその製法と使用 |
| DE10215292A1 (de) | 2002-02-19 | 2003-08-28 | Bayer Cropscience Ag | Disubstitutierte Pyrazolylcarbocanilide |
-
2003
- 2003-10-31 DE DE10351088A patent/DE10351088A1/de not_active Withdrawn
-
2004
- 2004-10-19 BR BRPI0416112-2A patent/BRPI0416112A/pt not_active IP Right Cessation
- 2004-10-19 US US10/576,742 patent/US7501527B2/en not_active Expired - Lifetime
- 2004-10-19 ES ES04765988.3T patent/ES2524597T3/es not_active Expired - Lifetime
- 2004-10-19 CN CN2004800322480A patent/CN1875006B/zh not_active Expired - Lifetime
- 2004-10-19 DK DK04765988.3T patent/DK1682515T3/en active
- 2004-10-19 JP JP2006537130A patent/JP4936895B2/ja not_active Expired - Lifetime
- 2004-10-19 WO PCT/EP2004/011809 patent/WO2005044804A1/de not_active Ceased
- 2004-10-19 EP EP04765988.3A patent/EP1682515B1/de not_active Expired - Lifetime
- 2004-10-19 KR KR1020067008293A patent/KR101123745B1/ko not_active Expired - Lifetime
- 2004-10-29 TW TW093132853A patent/TWI359141B/zh not_active IP Right Cessation
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2006
- 2006-04-25 IL IL175148A patent/IL175148A/en active IP Right Grant
- 2006-04-25 MX MXPA06004605 patent/MXPA06004605A/es active IP Right Grant
- 2006-09-06 IN IN1990DE2006 patent/IN2006DE01990A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IL175148A (en) | 2015-03-31 |
| IN2006DE01990A (enExample) | 2007-07-13 |
| JP4936895B2 (ja) | 2012-05-23 |
| JP2007509871A (ja) | 2007-04-19 |
| CN1875006B (zh) | 2011-12-21 |
| IL175148A0 (en) | 2006-09-05 |
| CN1875006A (zh) | 2006-12-06 |
| WO2005044804A1 (de) | 2005-05-19 |
| MXPA06004605A (es) | 2006-07-20 |
| KR20060094534A (ko) | 2006-08-29 |
| US20060276656A1 (en) | 2006-12-07 |
| EP1682515A1 (de) | 2006-07-26 |
| BRPI0416112A (pt) | 2007-01-02 |
| TW200530189A (en) | 2005-09-16 |
| TWI359141B (en) | 2012-03-01 |
| EP1682515B1 (de) | 2014-10-01 |
| US7501527B2 (en) | 2009-03-10 |
| KR101123745B1 (ko) | 2012-03-15 |
| DE10351088A1 (de) | 2005-06-02 |
| ES2524597T3 (es) | 2014-12-10 |
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