CN106554311B - 3-氟代烷基-1-甲基吡唑-4-羧酸的制备方法 - Google Patents
3-氟代烷基-1-甲基吡唑-4-羧酸的制备方法 Download PDFInfo
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- CN106554311B CN106554311B CN201510628810.6A CN201510628810A CN106554311B CN 106554311 B CN106554311 B CN 106554311B CN 201510628810 A CN201510628810 A CN 201510628810A CN 106554311 B CN106554311 B CN 106554311B
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- Prior art keywords
- fluoro
- alkyl
- carboxylic acid
- methyl
- methylpyrazole
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- 238000002360 preparation method Methods 0.000 title claims abstract description 29
- 238000006243 chemical reaction Methods 0.000 claims abstract description 41
- HDZGCSFEDULWCS-UHFFFAOYSA-N monomethylhydrazine Chemical group CNN HDZGCSFEDULWCS-UHFFFAOYSA-N 0.000 claims abstract description 18
- QPWSKIGAQZAJKS-UHFFFAOYSA-N 4-(dimethylamino)but-3-en-2-one Chemical compound CN(C)C=CC(C)=O QPWSKIGAQZAJKS-UHFFFAOYSA-N 0.000 claims abstract description 16
- 238000004519 manufacturing process Methods 0.000 claims abstract description 15
- 150000004820 halides Chemical class 0.000 claims abstract description 7
- 238000007363 ring formation reaction Methods 0.000 claims abstract description 6
- XVYFWBWYEAQLJC-UHFFFAOYSA-N 3,3-difluoropentane-2,4-dione Chemical class CC(=O)C(F)(F)C(C)=O XVYFWBWYEAQLJC-UHFFFAOYSA-N 0.000 claims abstract description 4
- 238000006482 condensation reaction Methods 0.000 claims abstract description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 69
- 239000000243 solution Substances 0.000 claims description 50
- 239000007789 gas Substances 0.000 claims description 34
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 23
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 20
- JQDCYDWZWBUECX-UHFFFAOYSA-N 3-(difluoromethyl)-1-methylpyrazole Chemical class CN1C=CC(C(F)F)=N1 JQDCYDWZWBUECX-UHFFFAOYSA-N 0.000 claims description 19
- 239000007864 aqueous solution Substances 0.000 claims description 14
- CVZIHXRHSDYALS-UHFFFAOYSA-N 1-fluoropentane-2,4-dione Chemical class CC(=O)CC(=O)CF CVZIHXRHSDYALS-UHFFFAOYSA-N 0.000 claims description 13
- 229910052731 fluorine Inorganic materials 0.000 claims description 11
- 239000011737 fluorine Substances 0.000 claims description 10
- 235000011121 sodium hydroxide Nutrition 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 230000035484 reaction time Effects 0.000 claims description 7
- -1 dimethylamino methylene Chemical group 0.000 claims description 6
- 150000002222 fluorine compounds Chemical class 0.000 claims description 6
- 230000020477 pH reduction Effects 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- CRWJEUDFKNYSBX-UHFFFAOYSA-N sodium;hypobromite Chemical compound [Na+].Br[O-] CRWJEUDFKNYSBX-UHFFFAOYSA-N 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 230000008859 change Effects 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 4
- 230000015572 biosynthetic process Effects 0.000 description 21
- 238000003786 synthesis reaction Methods 0.000 description 21
- 238000000034 method Methods 0.000 description 18
- 238000004587 chromatography analysis Methods 0.000 description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000010410 layer Substances 0.000 description 15
- 239000002994 raw material Substances 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- BEZVCXLDJHKSQE-UHFFFAOYSA-N 1-[3-(difluoromethyl)-1-methylpyrazol-4-yl]ethanone Chemical compound CC(=O)C1=CN(C)N=C1C(F)F BEZVCXLDJHKSQE-UHFFFAOYSA-N 0.000 description 10
- 239000012044 organic layer Substances 0.000 description 10
- 239000012467 final product Substances 0.000 description 8
- 239000012071 phase Substances 0.000 description 8
- 238000001035 drying Methods 0.000 description 7
- 239000007791 liquid phase Substances 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 6
- 230000008569 process Effects 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
- 238000000605 extraction Methods 0.000 description 5
- 238000004321 preservation Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000011084 recovery Methods 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- 239000012265 solid product Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- VHUXWJVMTRZXMT-UHFFFAOYSA-N 3-[chloro(difluoro)methyl]-1-methylpyrazole Chemical class CN1C=CC(C(F)(F)Cl)=N1 VHUXWJVMTRZXMT-UHFFFAOYSA-N 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- BHTZCIGVYSJBQB-UHFFFAOYSA-N 1-(1h-pyrazol-5-yl)ethanone Chemical compound CC(=O)C=1C=CNN=1 BHTZCIGVYSJBQB-UHFFFAOYSA-N 0.000 description 3
- MPBKAOHKPAKJDA-VCHYOVAHSA-N 2-(3-aminopropyl)-1-[(e)-(2,2-difluoro-1-phenylethylidene)amino]guanidine Chemical compound NCCCN=C(N)N\N=C(\C(F)F)C1=CC=CC=C1 MPBKAOHKPAKJDA-VCHYOVAHSA-N 0.000 description 3
- AZPWOLJQERBBBM-UHFFFAOYSA-N 2-chloro-2,2-difluoroacetyl chloride Chemical compound FC(F)(Cl)C(Cl)=O AZPWOLJQERBBBM-UHFFFAOYSA-N 0.000 description 3
- 238000003512 Claisen condensation reaction Methods 0.000 description 3
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 125000004494 ethyl ester group Chemical group 0.000 description 3
- TZMFJUDUGYTVRY-UHFFFAOYSA-N ethyl methyl diketone Natural products CCC(=O)C(C)=O TZMFJUDUGYTVRY-UHFFFAOYSA-N 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 230000014759 maintenance of location Effects 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000000575 pesticide Substances 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000002910 solid waste Substances 0.000 description 3
- 239000002351 wastewater Substances 0.000 description 3
- BXPYXUULYZZKNA-UHFFFAOYSA-N 1-[1-methyl-3-(trifluoromethyl)pyrazol-4-yl]ethanone Chemical compound CC(=O)C1=CN(C)N=C1C(F)(F)F BXPYXUULYZZKNA-UHFFFAOYSA-N 0.000 description 2
- DPBJAVGHACCNRL-UHFFFAOYSA-N 2-(dimethylamino)ethyl prop-2-enoate Chemical compound CN(C)CCOC(=O)C=C DPBJAVGHACCNRL-UHFFFAOYSA-N 0.000 description 2
- RLOHOBNEYHBZID-UHFFFAOYSA-N 3-(difluoromethyl)-1-methylpyrazole-4-carboxylic acid Chemical compound CN1C=C(C(O)=O)C(C(F)F)=N1 RLOHOBNEYHBZID-UHFFFAOYSA-N 0.000 description 2
- XTDZGXBTXBEZDN-UHFFFAOYSA-N 3-(difluoromethyl)-N-(9-isopropyl-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl)-1-methylpyrazole-4-carboxamide Chemical compound CC(C)C1C2CCC1C1=C2C=CC=C1NC(=O)C1=CN(C)N=C1C(F)F XTDZGXBTXBEZDN-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000005788 Fluxapyroxad Substances 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- 239000005799 Isopyrazam Substances 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-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
- 150000001412 amines Chemical class 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 125000001246 bromo group Chemical class Br* 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- FBCCMZVIWNDFMO-UHFFFAOYSA-N dichloroacetyl chloride Chemical compound ClC(Cl)C(Cl)=O FBCCMZVIWNDFMO-UHFFFAOYSA-N 0.000 description 2
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 2
- FMVJYQGSRWVMQV-UHFFFAOYSA-N ethyl propiolate Chemical compound CCOC(=O)C#C FMVJYQGSRWVMQV-UHFFFAOYSA-N 0.000 description 2
- SXSGXWCSHSVPGB-UHFFFAOYSA-N fluxapyroxad Chemical compound FC(F)C1=NN(C)C=C1C(=O)NC1=CC=CC=C1C1=CC(F)=C(F)C(F)=C1 SXSGXWCSHSVPGB-UHFFFAOYSA-N 0.000 description 2
- 230000000855 fungicidal effect Effects 0.000 description 2
- 239000000417 fungicide Substances 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 230000005311 nuclear magnetism Effects 0.000 description 2
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 238000010189 synthetic method Methods 0.000 description 2
- ZGOAEMCMBVUNMX-UHFFFAOYSA-N 1,1'-biphenyl;1h-pyrrole Chemical compound C=1C=CNC=1.C1=CC=CC=C1C1=CC=CC=C1 ZGOAEMCMBVUNMX-UHFFFAOYSA-N 0.000 description 1
- SHXHPUAKLCCLDV-UHFFFAOYSA-N 1,1,1-trifluoropentane-2,4-dione Chemical compound CC(=O)CC(=O)C(F)(F)F SHXHPUAKLCCLDV-UHFFFAOYSA-N 0.000 description 1
- MQSLINQSJFALSP-UHFFFAOYSA-N 1-methyl-3-(trifluoromethyl)pyrazole Chemical class CN1C=CC(C(F)(F)F)=N1 MQSLINQSJFALSP-UHFFFAOYSA-N 0.000 description 1
- FZNKJQNEJGXCJH-UHFFFAOYSA-N 1-methyl-3-(trifluoromethyl)pyrazole-4-carboxylic acid Chemical compound CN1C=C(C(O)=O)C(C(F)(F)F)=N1 FZNKJQNEJGXCJH-UHFFFAOYSA-N 0.000 description 1
- OETGCWJOUVQJSM-UHFFFAOYSA-N 3-ethoxyprop-2-enyl 3-oxobutanoate Chemical compound C(C)OC=CCOC(CC(=O)C)=O OETGCWJOUVQJSM-UHFFFAOYSA-N 0.000 description 1
- 239000005738 Bixafen Substances 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- XQJQCBDIXRIYRP-UHFFFAOYSA-N N-{2-[1,1'-bi(cyclopropyl)-2-yl]phenyl}-3-(difluoromethyl)-1-methyl-1pyrazole-4-carboxamide Chemical compound FC(F)C1=NN(C)C=C1C(=O)NC1=CC=CC=C1C1C(C2CC2)C1 XQJQCBDIXRIYRP-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 239000005834 Sedaxane Substances 0.000 description 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- WHDHEVMINMZADQ-UHFFFAOYSA-N [F].N1C=CC=C1 Chemical group [F].N1C=CC=C1 WHDHEVMINMZADQ-UHFFFAOYSA-N 0.000 description 1
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical class CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- ILRRQNADMUWWFW-UHFFFAOYSA-K aluminium phosphate Chemical class O1[Al]2OP1(=O)O2 ILRRQNADMUWWFW-UHFFFAOYSA-K 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 150000003851 azoles Chemical class 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- LDLMOOXUCMHBMZ-UHFFFAOYSA-N bixafen Chemical compound FC(F)C1=NN(C)C=C1C(=O)NC1=CC=C(F)C=C1C1=CC=C(Cl)C(Cl)=C1 LDLMOOXUCMHBMZ-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000006298 dechlorination reaction Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- PBWZKZYHONABLN-UHFFFAOYSA-N difluoroacetic acid Chemical compound OC(=O)C(F)F PBWZKZYHONABLN-UHFFFAOYSA-N 0.000 description 1
- 125000006001 difluoroethyl group Chemical group 0.000 description 1
- XHFGWHUWQXTGAT-UHFFFAOYSA-N dimethylamine hydrochloride Natural products CNC(C)C XHFGWHUWQXTGAT-UHFFFAOYSA-N 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- IQDGSYLLQPDQDV-UHFFFAOYSA-N dimethylazanium;chloride Chemical compound Cl.CNC IQDGSYLLQPDQDV-UHFFFAOYSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- IWYBVQLPTCMVFO-UHFFFAOYSA-N ethyl 2,2-dichloroacetate Chemical compound CCOC(=O)C(Cl)Cl IWYBVQLPTCMVFO-UHFFFAOYSA-N 0.000 description 1
- 230000000763 evoking effect Effects 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 1
- 230000008676 import Effects 0.000 description 1
- 229910001506 inorganic fluoride Inorganic materials 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- PQIOSYKVBBWRRI-UHFFFAOYSA-N methylphosphonyl difluoride Chemical group CP(F)(F)=O PQIOSYKVBBWRRI-UHFFFAOYSA-N 0.000 description 1
- NINOYJQVULROET-UHFFFAOYSA-N n,n-dimethylethenamine Chemical group CN(C)C=C NINOYJQVULROET-UHFFFAOYSA-N 0.000 description 1
- NXBBFAKHXAMPOM-UHFFFAOYSA-N n,n-dimethylprop-1-en-1-amine Chemical group CC=CN(C)C NXBBFAKHXAMPOM-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 238000007539 photo-oxidation reaction Methods 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 235000003270 potassium fluoride Nutrition 0.000 description 1
- 239000011698 potassium fluoride Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000010183 spectrum analysis Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- PNQBEPDZQUOCNY-UHFFFAOYSA-N trifluoroacetyl chloride Chemical compound FC(F)(F)C(Cl)=O PNQBEPDZQUOCNY-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 238000012795 verification Methods 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Description
峰号 | 保留时间(min) | 峰高 | 峰面积 | 含量(%) |
1 | 7.998 | 302654.188 | 1048392.313 | 100.0000 |
总计 | 7.998 | 302654.188 | 1048392.313 | 100.0000 |
峰号 | 保留时间(min) | 峰高 | 峰面积 | 含量(%) |
1 | 3.350 | 1483.95544 | 8274.68066 | 100.0000 |
总计 | 3.350 | 1483.95544 | 8274.68066 | 100.0000 |
峰号 | 保留时间(min) | 峰高 | 峰面积 | 含量(%) |
1 | 2.172 | 417.05890 | 3670.01538 | 100.0000 |
总计 | 2.172 | 417.05890 | 3670.01538 | 100.0000 |
Claims (9)
Priority Applications (1)
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CN201510628810.6A CN106554311B (zh) | 2015-09-28 | 2015-09-28 | 3-氟代烷基-1-甲基吡唑-4-羧酸的制备方法 |
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CN201510628810.6A CN106554311B (zh) | 2015-09-28 | 2015-09-28 | 3-氟代烷基-1-甲基吡唑-4-羧酸的制备方法 |
Publications (2)
Publication Number | Publication Date |
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CN106554311A CN106554311A (zh) | 2017-04-05 |
CN106554311B true CN106554311B (zh) | 2019-03-01 |
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CN (1) | CN106554311B (zh) |
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CN117384096A (zh) * | 2023-12-13 | 2024-01-12 | 山东国邦药业有限公司 | 一种二氟吡唑酸的制备方法 |
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DE102005007160A1 (de) * | 2005-02-16 | 2006-08-24 | Basf Ag | Pyrazolcarbonsäureanilide, Verfahren zu ihrer Herstellung und sie enthaltende Mittel zur Bekämpfung von Schadpilzen |
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 |
JP5559066B2 (ja) * | 2008-02-29 | 2014-07-23 | ビーエーエスエフ ソシエタス・ヨーロピア | 2−アルコキシメチレン−4,4−ジフルオロ−3−オキソ酪酸アルキルの製造方法 |
EP2297111B1 (de) * | 2008-05-02 | 2012-06-20 | Basf Se | Verfahren zur herstellung halogensubstituierter 2-(aminomethyliden)-3-oxobuttersäureester |
US8314233B2 (en) * | 2008-05-02 | 2012-11-20 | Basf Se | Process for preparing 2-(aminomethylidene)-4,4-difluoro-3-oxobutyric esters |
WO2012025469A1 (en) * | 2010-08-24 | 2012-03-01 | Solvay Sa | Improved process for the preparation of esters of 1-h-pyrazole-4-carboxylic acids |
CN103360313A (zh) * | 2013-07-12 | 2013-10-23 | 雅本化学股份有限公司 | 3-氟代烷基-1-取代吡唑-4-羧酸及其制备方法 |
CN104163800B (zh) * | 2014-08-19 | 2016-09-28 | 一帆生物科技集团有限公司 | 一种3-二氟甲基-1-甲基-1h-吡唑-4-羧酸的制备方法 |
CN104326975A (zh) * | 2014-10-20 | 2015-02-04 | 郑州四环医药用品有限公司 | 一种高纯度米力农的制备方法 |
CN104496903A (zh) * | 2014-12-19 | 2015-04-08 | 浙江泰达作物科技有限公司 | 1-烷基-3-卤代烷基吡唑衍生物的高区域选择性的合成方法 |
CN105541716B (zh) * | 2015-03-26 | 2024-02-23 | Agc株式会社 | 吡唑衍生物的制造方法 |
CN106554310A (zh) * | 2015-09-25 | 2017-04-05 | 陈旭 | 一种3-二氟甲基-1-甲基吡唑-4-甲酸的合成方法 |
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