CA2545452C - Ortho-substituted pentafluoride sulfanyl-benzenes, method for the production thereof and the use thereof in the form of valuable synthesis intermediate stages - Google Patents
Ortho-substituted pentafluoride sulfanyl-benzenes, method for the production thereof and the use thereof in the form of valuable synthesis intermediate stages Download PDFInfo
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- CA2545452C CA2545452C CA2545452A CA2545452A CA2545452C CA 2545452 C CA2545452 C CA 2545452C CA 2545452 A CA2545452 A CA 2545452A CA 2545452 A CA2545452 A CA 2545452A CA 2545452 C CA2545452 C CA 2545452C
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- Prior art keywords
- carbon atoms
- zero
- alkyl
- hydrogen
- formula
- Prior art date
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- 238000004519 manufacturing process Methods 0.000 title claims description 4
- NZEPCOFOZRNURX-UHFFFAOYSA-N F.F.F.F.F.SC1=CC=CC=C1 Chemical class F.F.F.F.F.SC1=CC=CC=C1 NZEPCOFOZRNURX-UHFFFAOYSA-N 0.000 title abstract description 3
- 238000000034 method Methods 0.000 title description 7
- 230000015572 biosynthetic process Effects 0.000 title description 2
- 238000003786 synthesis reaction Methods 0.000 title description 2
- 230000000895 acaricidal effect Effects 0.000 claims abstract description 5
- 239000000642 acaricide Substances 0.000 claims abstract description 5
- 239000003814 drug Substances 0.000 claims abstract description 5
- 239000004009 herbicide Substances 0.000 claims abstract description 5
- 239000004973 liquid crystal related substance Substances 0.000 claims abstract description 5
- 230000000590 parasiticidal effect Effects 0.000 claims abstract description 5
- 239000002297 parasiticide Substances 0.000 claims abstract description 5
- 229920000642 polymer Polymers 0.000 claims abstract description 5
- 239000002917 insecticide Substances 0.000 claims abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 180
- 125000000217 alkyl group Chemical group 0.000 claims description 85
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 71
- 229910052801 chlorine Inorganic materials 0.000 claims description 62
- 229910052731 fluorine Inorganic materials 0.000 claims description 59
- 150000001875 compounds Chemical class 0.000 claims description 58
- 229910052794 bromium Inorganic materials 0.000 claims description 56
- 229910052739 hydrogen Inorganic materials 0.000 claims description 56
- 239000001257 hydrogen Substances 0.000 claims description 55
- 229910052740 iodine Inorganic materials 0.000 claims description 53
- 125000003545 alkoxy group Chemical group 0.000 claims description 48
- -1 R14 is OH Chemical group 0.000 claims description 38
- 150000002431 hydrogen Chemical group 0.000 claims description 38
- 125000001424 substituent group Chemical group 0.000 claims description 27
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 22
- 125000001153 fluoro group Chemical group F* 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 17
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 16
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 16
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims description 13
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 11
- 125000000623 heterocyclic group Chemical group 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 8
- 239000000417 fungicide Substances 0.000 claims description 4
- 239000005645 nematicide Substances 0.000 claims description 4
- 239000000575 pesticide Substances 0.000 claims description 4
- 238000007345 electrophilic aromatic substitution reaction Methods 0.000 claims description 3
- 239000000543 intermediate Substances 0.000 abstract description 6
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 238000003745 diagnosis Methods 0.000 abstract 1
- 229940079593 drug Drugs 0.000 abstract 1
- 230000000855 fungicidal effect Effects 0.000 abstract 1
- 230000001069 nematicidal effect Effects 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 description 55
- 239000000203 mixture Substances 0.000 description 43
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 21
- 239000002904 solvent Substances 0.000 description 19
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 16
- 238000001035 drying Methods 0.000 description 15
- 239000000741 silica gel Substances 0.000 description 15
- 229910002027 silica gel Inorganic materials 0.000 description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 11
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 11
- 235000019341 magnesium sulphate Nutrition 0.000 description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 11
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000004587 chromatography analysis Methods 0.000 description 9
- 229910017604 nitric acid Inorganic materials 0.000 description 9
- 239000003921 oil Substances 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- 239000007832 Na2SO4 Substances 0.000 description 8
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- 229910052938 sodium sulfate Inorganic materials 0.000 description 8
- 235000011152 sodium sulphate Nutrition 0.000 description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
- 238000000605 extraction Methods 0.000 description 7
- 239000012074 organic phase Substances 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- DEMFWRJSKIDGJG-UHFFFAOYSA-N n-[4-nitro-3-(pentafluoro-$l^{6}-sulfanyl)phenyl]acetamide Chemical compound CC(=O)NC1=CC=C([N+]([O-])=O)C(S(F)(F)(F)(F)F)=C1 DEMFWRJSKIDGJG-UHFFFAOYSA-N 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 229920006395 saturated elastomer Polymers 0.000 description 6
- OQGXLFIPZRPECI-UHFFFAOYSA-N 2-chloro-5-(pentafluoro-$l^{6}-sulfanyl)aniline Chemical compound NC1=CC(S(F)(F)(F)(F)F)=CC=C1Cl OQGXLFIPZRPECI-UHFFFAOYSA-N 0.000 description 5
- 229910021575 Iron(II) bromide Inorganic materials 0.000 description 5
- 239000008346 aqueous phase Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000012230 colorless oil Substances 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- GYCHYNMREWYSKH-UHFFFAOYSA-L iron(ii) bromide Chemical compound [Fe+2].[Br-].[Br-] GYCHYNMREWYSKH-UHFFFAOYSA-L 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- MZGZUHNSMNNSRJ-UHFFFAOYSA-N 4-(pentafluoro-$l^{6}-sulfanyl)aniline Chemical compound NC1=CC=C(S(F)(F)(F)(F)F)C=C1 MZGZUHNSMNNSRJ-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
- 229910004373 HOAc Inorganic materials 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 235000019439 ethyl acetate Nutrition 0.000 description 4
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 4
- HKCHKCDGYHAANS-UHFFFAOYSA-N methyl 3-amino-4-chloro-5-(pentafluoro-$l^{6}-sulfanyl)benzoate Chemical compound COC(=O)C1=CC(N)=C(Cl)C(S(F)(F)(F)(F)F)=C1 HKCHKCDGYHAANS-UHFFFAOYSA-N 0.000 description 4
- FVZHFGQDMRDHBE-UHFFFAOYSA-N n-[2-nitro-5-(pentafluoro-$l^{6}-sulfanyl)phenyl]acetamide Chemical compound CC(=O)NC1=CC(S(F)(F)(F)(F)F)=CC=C1[N+]([O-])=O FVZHFGQDMRDHBE-UHFFFAOYSA-N 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 4
- 235000010265 sodium sulphite Nutrition 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 235000011149 sulphuric acid Nutrition 0.000 description 4
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 3
- UHCDSBCWEGNEHL-UHFFFAOYSA-N 2-[2-nitro-5-(pentafluoro-$l^{6}-sulfanyl)phenyl]isoindole-1,3-dione Chemical compound [O-][N+](=O)C1=CC=C(S(F)(F)(F)(F)F)C=C1N1C(=O)C2=CC=CC=C2C1=O UHCDSBCWEGNEHL-UHFFFAOYSA-N 0.000 description 3
- YJACJRMRGHEXFP-UHFFFAOYSA-N 2-[3-(pentafluoro-$l^{6}-sulfanyl)phenyl]isoindole-1,3-dione Chemical compound FS(F)(F)(F)(F)C1=CC=CC(N2C(C3=CC=CC=C3C2=O)=O)=C1 YJACJRMRGHEXFP-UHFFFAOYSA-N 0.000 description 3
- OUMUBZIEVXBBAY-UHFFFAOYSA-N 2-[4-amino-3-(pentafluoro-$l^{6}-sulfanyl)phenyl]isoindole-1,3-dione Chemical compound C1=C(S(F)(F)(F)(F)F)C(N)=CC=C1N1C(=O)C2=CC=CC=C2C1=O OUMUBZIEVXBBAY-UHFFFAOYSA-N 0.000 description 3
- JMCNCDUVHZWBBI-UHFFFAOYSA-N 2-[4-nitro-3-(pentafluoro-$l^{6}-sulfanyl)phenyl]isoindole-1,3-dione Chemical compound C1=C(S(F)(F)(F)(F)F)C([N+](=O)[O-])=CC=C1N1C(=O)C2=CC=CC=C2C1=O JMCNCDUVHZWBBI-UHFFFAOYSA-N 0.000 description 3
- BYEXDMPBPSYTNU-UHFFFAOYSA-N 2-bromo-4-(pentafluoro-$l^{6}-sulfanyl)aniline Chemical compound NC1=CC=C(S(F)(F)(F)(F)F)C=C1Br BYEXDMPBPSYTNU-UHFFFAOYSA-N 0.000 description 3
- OSSOGWQGUMFSHP-UHFFFAOYSA-N 2-chloro-3-(pentafluoro-$l^{6}-sulfanyl)aniline Chemical compound NC1=CC=CC(S(F)(F)(F)(F)F)=C1Cl OSSOGWQGUMFSHP-UHFFFAOYSA-N 0.000 description 3
- SCWBHSDSPRGLKE-UHFFFAOYSA-N 2-methyl-4-(pentafluoro-$l^{6}-sulfanyl)aniline Chemical compound CC1=CC(S(F)(F)(F)(F)F)=CC=C1N SCWBHSDSPRGLKE-UHFFFAOYSA-N 0.000 description 3
- ZKSBHVYQJGEVPY-UHFFFAOYSA-N 2-methyl-4-(pentafluoro-$l^{6}-sulfanyl)benzoic acid Chemical compound CC1=CC(S(F)(F)(F)(F)F)=CC=C1C(O)=O ZKSBHVYQJGEVPY-UHFFFAOYSA-N 0.000 description 3
- XHJLGVIUMCBMHL-UHFFFAOYSA-N 4-(pentafluoro-$l^{6}-sulfanyl)phenol Chemical compound OC1=CC=C(S(F)(F)(F)(F)F)C=C1 XHJLGVIUMCBMHL-UHFFFAOYSA-N 0.000 description 3
- LZJNVJWNZZTFIS-UHFFFAOYSA-N 4-chloro-3-(pentafluoro-$l^{6}-sulfanyl)aniline Chemical compound NC1=CC=C(Cl)C(S(F)(F)(F)(F)F)=C1 LZJNVJWNZZTFIS-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical class OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- HRPDSARDVSAIAS-UHFFFAOYSA-N methyl 5-amino-2-chloro-3-(pentafluoro-$l^{6}-sulfanyl)benzoate Chemical compound COC(=O)C1=CC(N)=CC(S(F)(F)(F)(F)F)=C1Cl HRPDSARDVSAIAS-UHFFFAOYSA-N 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- XLSGELXHPBMZBG-UHFFFAOYSA-N n-[2,4-dinitro-5-(pentafluoro-$l^{6}-sulfanyl)phenyl]acetamide Chemical compound CC(=O)NC1=CC(S(F)(F)(F)(F)F)=C([N+]([O-])=O)C=C1[N+]([O-])=O XLSGELXHPBMZBG-UHFFFAOYSA-N 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 235000015320 potassium carbonate Nutrition 0.000 description 3
- GDUXGSGWLIGRBT-UHFFFAOYSA-N (3,5-dibromo-4-methoxy-2-nitrophenyl)-pentafluoro-$l^{6}-sulfane Chemical compound COC1=C(Br)C=C(S(F)(F)(F)(F)F)C([N+]([O-])=O)=C1Br GDUXGSGWLIGRBT-UHFFFAOYSA-N 0.000 description 2
- WYSXPOPCPHVGBJ-UHFFFAOYSA-N (3,5-dibromo-4-methoxyphenyl)-pentafluoro-$l^{6}-sulfane Chemical compound COC1=C(Br)C=C(S(F)(F)(F)(F)F)C=C1Br WYSXPOPCPHVGBJ-UHFFFAOYSA-N 0.000 description 2
- FTJCIMJCCNRUEN-UHFFFAOYSA-N (3-bromo-5-chloro-4-methoxy-2-nitrophenyl)-pentafluoro-$l^{6}-sulfane Chemical compound COC1=C(Cl)C=C(S(F)(F)(F)(F)F)C([N+]([O-])=O)=C1Br FTJCIMJCCNRUEN-UHFFFAOYSA-N 0.000 description 2
- YPXGGVCYCAKTDN-UHFFFAOYSA-N (3-bromo-5-chloro-4-methoxyphenyl)-pentafluoro-$l^{6}-sulfane Chemical compound COC1=C(Cl)C=C(S(F)(F)(F)(F)F)C=C1Br YPXGGVCYCAKTDN-UHFFFAOYSA-N 0.000 description 2
- HDXQQPIDMAWIEY-UHFFFAOYSA-N (3-chloro-4-methoxyphenyl)-pentafluoro-$l^{6}-sulfane Chemical compound COC1=CC=C(S(F)(F)(F)(F)F)C=C1Cl HDXQQPIDMAWIEY-UHFFFAOYSA-N 0.000 description 2
- QNBZHUMTLPWQDX-UHFFFAOYSA-N (4-bromo-3-methylphenyl)-pentafluoro-$l^{6}-sulfane Chemical compound CC1=CC(S(F)(F)(F)(F)F)=CC=C1Br QNBZHUMTLPWQDX-UHFFFAOYSA-N 0.000 description 2
- QYIUHTUUVWXEMY-UHFFFAOYSA-N (5-bromo-3-chloro-4-methoxy-2-nitrophenyl)-pentafluoro-$l^{6}-sulfane Chemical compound COC1=C(Br)C=C(S(F)(F)(F)(F)F)C([N+]([O-])=O)=C1Cl QYIUHTUUVWXEMY-UHFFFAOYSA-N 0.000 description 2
- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 description 2
- XLHNMWUTNDIEHS-UHFFFAOYSA-N 2,6-dibromo-4-(pentafluoro-$l^{6}-sulfanyl)phenol Chemical compound OC1=C(Br)C=C(S(F)(F)(F)(F)F)C=C1Br XLHNMWUTNDIEHS-UHFFFAOYSA-N 0.000 description 2
- SGPBHHISVFGANI-UHFFFAOYSA-N 2-chloro-4-(pentafluoro-$l^{6}-sulfanyl)phenol Chemical compound OC1=CC=C(S(F)(F)(F)(F)F)C=C1Cl SGPBHHISVFGANI-UHFFFAOYSA-N 0.000 description 2
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 2
- LMGRMVMKKDDFLW-UHFFFAOYSA-N 2-methyl-4-(pentafluoro-$l^{6}-sulfanyl)benzonitrile Chemical compound CC1=CC(S(F)(F)(F)(F)F)=CC=C1C#N LMGRMVMKKDDFLW-UHFFFAOYSA-N 0.000 description 2
- HMBPVMYAGVDUOW-UHFFFAOYSA-N 2-methyl-5-nitro-4-(pentafluoro-$l^{6}-sulfanyl)benzoic acid Chemical compound CC1=CC(S(F)(F)(F)(F)F)=C([N+]([O-])=O)C=C1C(O)=O HMBPVMYAGVDUOW-UHFFFAOYSA-N 0.000 description 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 description 2
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 2
- NUFLICUHOXHWER-UHFFFAOYSA-N 3-(pentafluoro-$l^{6}-sulfanyl)aniline Chemical compound NC1=CC=CC(S(F)(F)(F)(F)F)=C1 NUFLICUHOXHWER-UHFFFAOYSA-N 0.000 description 2
- AKFDIYXSRGLRAB-UHFFFAOYSA-N 3-(pentafluoro-$l^{6}-sulfanyl)benzoic acid Chemical compound OC(=O)C1=CC=CC(S(F)(F)(F)(F)F)=C1 AKFDIYXSRGLRAB-UHFFFAOYSA-N 0.000 description 2
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 2
- NHOUZLDRSXONNF-UHFFFAOYSA-N 3-nitro-5-(pentafluoro-$l^{6}-sulfanyl)benzoic acid Chemical compound OC(=O)C1=CC([N+]([O-])=O)=CC(S(F)(F)(F)(F)F)=C1 NHOUZLDRSXONNF-UHFFFAOYSA-N 0.000 description 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 2
- 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 description 2
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 2
- ROVDVRMPJIFSKW-UHFFFAOYSA-N 4-(1,3-dioxoisoindol-2-yl)-2-(pentafluoro-$l^{6}-sulfanyl)benzonitrile Chemical compound C1=C(C#N)C(S(F)(F)(F)(F)F)=CC(N2C(C3=CC=CC=C3C2=O)=O)=C1 ROVDVRMPJIFSKW-UHFFFAOYSA-N 0.000 description 2
- WMBSDNUINSRVBS-UHFFFAOYSA-N 4-amino-2-(pentafluoro-$l^{6}-sulfanyl)benzonitrile Chemical compound NC1=CC=C(C#N)C(S(F)(F)(F)(F)F)=C1 WMBSDNUINSRVBS-UHFFFAOYSA-N 0.000 description 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001448 anilines Chemical class 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- QTMDXZNDVAMKGV-UHFFFAOYSA-L copper(ii) bromide Chemical compound [Cu+2].[Br-].[Br-] QTMDXZNDVAMKGV-UHFFFAOYSA-L 0.000 description 2
- NXQGGXCHGDYOHB-UHFFFAOYSA-L cyclopenta-1,4-dien-1-yl(diphenyl)phosphane;dichloropalladium;iron(2+) Chemical compound [Fe+2].Cl[Pd]Cl.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 NXQGGXCHGDYOHB-UHFFFAOYSA-L 0.000 description 2
- 239000000428 dust Substances 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 230000026030 halogenation Effects 0.000 description 2
- 238000005658 halogenation reaction Methods 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- HHGHVHKCBCUYFU-UHFFFAOYSA-N methyl 3-amino-2-chloro-5-(pentafluoro-$l^{6}-sulfanyl)benzoate Chemical compound COC(=O)C1=CC(S(F)(F)(F)(F)F)=CC(N)=C1Cl HHGHVHKCBCUYFU-UHFFFAOYSA-N 0.000 description 2
- DEPIWPSMRGGLGG-UHFFFAOYSA-N methyl 3-amino-5-(pentafluoro-$l^{6}-sulfanyl)benzoate Chemical compound COC(=O)C1=CC(N)=CC(S(F)(F)(F)(F)F)=C1 DEPIWPSMRGGLGG-UHFFFAOYSA-N 0.000 description 2
- KGJYIFQVGPYWLJ-UHFFFAOYSA-N methyl 3-nitro-5-(pentafluoro-$l^{6}-sulfanyl)benzoate Chemical compound COC(=O)C1=CC([N+]([O-])=O)=CC(S(F)(F)(F)(F)F)=C1 KGJYIFQVGPYWLJ-UHFFFAOYSA-N 0.000 description 2
- DFEAUHMFQHNGRN-UHFFFAOYSA-N n-[3-(pentafluoro-$l^{6}-sulfanyl)phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC(S(F)(F)(F)(F)F)=C1 DFEAUHMFQHNGRN-UHFFFAOYSA-N 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 238000006396 nitration reaction Methods 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- DMNYFEWFSFTYEL-UHFFFAOYSA-N pentafluoro(phenyl)-$l^{6}-sulfane Chemical class FS(F)(F)(F)(F)C1=CC=CC=C1 DMNYFEWFSFTYEL-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 2
- 125000004944 pyrazin-3-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 2
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 description 2
- 125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 description 2
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 2
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 2
- 125000004943 pyrimidin-6-yl group Chemical group N1=CN=CC=C1* 0.000 description 2
- KWVVTSALYXIJSS-UHFFFAOYSA-L silver(ii) fluoride Chemical compound [F-].[F-].[Ag+2] KWVVTSALYXIJSS-UHFFFAOYSA-L 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017550 sodium carbonate Nutrition 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 125000004434 sulfur atom Chemical group 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 230000009466 transformation Effects 0.000 description 2
- 238000000844 transformation Methods 0.000 description 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- YIMOAXFUQLPTCU-UHFFFAOYSA-N (3,4-dibromo-5-methylphenyl)-pentafluoro-$l^{6}-sulfane Chemical compound CC1=CC(S(F)(F)(F)(F)F)=CC(Br)=C1Br YIMOAXFUQLPTCU-UHFFFAOYSA-N 0.000 description 1
- 125000004509 1,3,4-oxadiazol-2-yl group Chemical group O1C(=NN=C1)* 0.000 description 1
- 125000004510 1,3,4-oxadiazol-5-yl group Chemical group O1C=NN=C1* 0.000 description 1
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- XUVHCEGOKVEAGV-UHFFFAOYSA-N 2,3,4,8,9,10-hexahydropyrimido[1,2-a]azepine Chemical compound C1CCC=CN2CCCN=C21 XUVHCEGOKVEAGV-UHFFFAOYSA-N 0.000 description 1
- GBBSAMQTQCPOBF-UHFFFAOYSA-N 2,4,6-trimethyl-1,3,5,2,4,6-trioxatriborinane Chemical compound CB1OB(C)OB(C)O1 GBBSAMQTQCPOBF-UHFFFAOYSA-N 0.000 description 1
- BEJBOKHTCYBCMC-UHFFFAOYSA-N 2-[4-(hydroxyamino)-3-(pentafluoro-$l^{6}-sulfanyl)phenyl]isoindole-1,3-dione Chemical compound C1=C(S(F)(F)(F)(F)F)C(NO)=CC=C1N1C(=O)C2=CC=CC=C2C1=O BEJBOKHTCYBCMC-UHFFFAOYSA-N 0.000 description 1
- BNDDLCDSFJANNS-UHFFFAOYSA-N 2-[[4-cyano-3-(pentafluoro-lambda6-sulfanyl)phenyl]carbamoyl]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)NC1=CC=C(C#N)C(S(F)(F)(F)(F)F)=C1 BNDDLCDSFJANNS-UHFFFAOYSA-N 0.000 description 1
- APWZGITUCNKHNJ-UHFFFAOYSA-N 2-bromo-6-chloro-4-(pentafluoro-$l^{6}-sulfanyl)phenol Chemical compound OC1=C(Cl)C=C(S(F)(F)(F)(F)F)C=C1Br APWZGITUCNKHNJ-UHFFFAOYSA-N 0.000 description 1
- HEGSQWSMVLVDBR-UHFFFAOYSA-N 2-chloro-4-nitro-5-(pentafluoro-$l^{6}-sulfanyl)aniline Chemical compound NC1=CC(S(F)(F)(F)(F)F)=C([N+]([O-])=O)C=C1Cl HEGSQWSMVLVDBR-UHFFFAOYSA-N 0.000 description 1
- KDDQRKBRJSGMQE-UHFFFAOYSA-N 4-thiazolyl Chemical compound [C]1=CSC=N1 KDDQRKBRJSGMQE-UHFFFAOYSA-N 0.000 description 1
- 125000004539 5-benzimidazolyl group Chemical group N1=CNC2=C1C=CC(=C2)* 0.000 description 1
- CWDWFSXUQODZGW-UHFFFAOYSA-N 5-thiazolyl Chemical group [C]1=CN=CS1 CWDWFSXUQODZGW-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 0 Cc1c(*)c(*)c(*)c(*)c1S(F)(F)(F)(F)F Chemical compound Cc1c(*)c(*)c(*)c(*)c1S(F)(F)(F)(F)F 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- OCUCCJIRFHNWBP-IYEMJOQQSA-L Copper gluconate Chemical class [Cu+2].OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O OCUCCJIRFHNWBP-IYEMJOQQSA-L 0.000 description 1
- 229910021590 Copper(II) bromide Inorganic materials 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-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
- 206010013786 Dry skin Diseases 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-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
- 150000001204 N-oxides Chemical class 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- ZCHPKWUIAASXPV-UHFFFAOYSA-N acetic acid;methanol Chemical compound OC.CC(O)=O ZCHPKWUIAASXPV-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical class OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical class OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Substances N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
- 150000001860 citric acid derivatives Chemical class 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- XTVVROIMIGLXTD-UHFFFAOYSA-N copper(II) nitrate Inorganic materials [Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O XTVVROIMIGLXTD-UHFFFAOYSA-N 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 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
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([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
- VRLDVERQJMEPIF-UHFFFAOYSA-N dbdmh Chemical compound CC1(C)N(Br)C(=O)N(Br)C1=O VRLDVERQJMEPIF-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 1
- ZOZMAORCJPPGBJ-UHFFFAOYSA-N ethyl 2-[[4-cyano-3-(pentafluoro-$l^{6}-sulfanyl)phenyl]carbamoyl]benzoate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)NC1=CC=C(C#N)C(S(F)(F)(F)(F)F)=C1 ZOZMAORCJPPGBJ-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 150000002306 glutamic acid derivatives Chemical class 0.000 description 1
- AWUCVROLDVIAJX-UHFFFAOYSA-N glycerol 1-phosphate Chemical class OCC(O)COP(O)(O)=O AWUCVROLDVIAJX-UHFFFAOYSA-N 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 150000003893 lactate salts Chemical class 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- QWDHRNPGSCABEC-UHFFFAOYSA-N methyl 3-amino-6-chloro-3-(pentafluoro-$l^{6}-sulfanyl)cyclohexa-1,5-diene-1-carboxylate Chemical compound COC(=O)C1=CC(N)(S(F)(F)(F)(F)F)CC=C1Cl QWDHRNPGSCABEC-UHFFFAOYSA-N 0.000 description 1
- 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- WOOWBQQQJXZGIE-UHFFFAOYSA-N n-ethyl-n-propan-2-ylpropan-2-amine Chemical compound CCN(C(C)C)C(C)C.CCN(C(C)C)C(C)C WOOWBQQQJXZGIE-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- OPPXUPGOUVHFHM-UHFFFAOYSA-N pentafluoro-(3-iodophenyl)-$l^{6}-sulfane Chemical compound FS(F)(F)(F)(F)C1=CC=CC(I)=C1 OPPXUPGOUVHFHM-UHFFFAOYSA-N 0.000 description 1
- HVEWPNYILHLGKS-UHFFFAOYSA-N pentafluoro-(4-methoxyphenyl)-$l^{6}-sulfane Chemical compound COC1=CC=C(S(F)(F)(F)(F)F)C=C1 HVEWPNYILHLGKS-UHFFFAOYSA-N 0.000 description 1
- AGNCKMHGYZKMLN-UHFFFAOYSA-N pentafluoro-(4-nitrophenyl)-$l^{6}-sulfane Chemical compound [O-][N+](=O)C1=CC=C(S(F)(F)(F)(F)F)C=C1 AGNCKMHGYZKMLN-UHFFFAOYSA-N 0.000 description 1
- 125000003884 phenylalkyl group Chemical group 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 238000000524 positive electrospray ionisation mass spectrometry Methods 0.000 description 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000002953 preparative HPLC Methods 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 102220229647 rs752205710 Human genes 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
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- IOGXOCVLYRDXLW-UHFFFAOYSA-N tert-butyl nitrite Chemical compound CC(C)(C)ON=O IOGXOCVLYRDXLW-UHFFFAOYSA-N 0.000 description 1
- 239000012414 tert-butyl nitrite Substances 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 238000002604 ultrasonography Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C381/00—Compounds containing carbon and sulfur and having functional groups not covered by groups C07C301/00 - C07C337/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Indole Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10353205A DE10353205A1 (de) | 2003-11-13 | 2003-11-13 | Ortho-substituierte Pentafluorsulfuranyl-Benzole, Verfahren zu ihrer Herstellung sowie ihre Verwendung als wertvolle Synthese-Zwischenstufen |
| DE10353205.6 | 2003-11-13 | ||
| PCT/EP2004/012394 WO2005047240A1 (de) | 2003-11-13 | 2004-11-03 | Ortho-substituierte pentafluorsulfanyl-benzole, verfahren zu ihrer herstellung sowie ihre verwendung ais wertvolle synthese-zwischenstufen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2545452A1 CA2545452A1 (en) | 2005-05-26 |
| CA2545452C true CA2545452C (en) | 2013-01-08 |
Family
ID=34585096
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2545452A Expired - Fee Related CA2545452C (en) | 2003-11-13 | 2004-11-03 | Ortho-substituted pentafluoride sulfanyl-benzenes, method for the production thereof and the use thereof in the form of valuable synthesis intermediate stages |
Country Status (24)
| Country | Link |
|---|---|
| EP (1) | EP1685098B1 (enExample) |
| JP (1) | JP4516968B2 (enExample) |
| KR (1) | KR101165583B1 (enExample) |
| CN (1) | CN100579960C (enExample) |
| AR (1) | AR046619A1 (enExample) |
| AT (1) | ATE464288T1 (enExample) |
| AU (1) | AU2004288759B2 (enExample) |
| BR (1) | BRPI0416031A (enExample) |
| CA (1) | CA2545452C (enExample) |
| CO (1) | CO5690545A2 (enExample) |
| DE (2) | DE10353205A1 (enExample) |
| DK (1) | DK1685098T3 (enExample) |
| ES (1) | ES2344296T3 (enExample) |
| IL (1) | IL175239A (enExample) |
| MY (1) | MY143530A (enExample) |
| NO (1) | NO20062701L (enExample) |
| NZ (1) | NZ547171A (enExample) |
| PE (1) | PE20050493A1 (enExample) |
| PT (1) | PT1685098E (enExample) |
| RU (1) | RU2372332C2 (enExample) |
| TW (1) | TWI334412B (enExample) |
| UY (1) | UY28615A1 (enExample) |
| WO (1) | WO2005047240A1 (enExample) |
| ZA (1) | ZA200602578B (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102006036023A1 (de) | 2006-08-02 | 2008-02-07 | Sanofi-Aventis | Imino-imidazo-pyridinderivate mit antithrombotischer Aktivität |
| AU2008212594C1 (en) * | 2007-02-09 | 2013-04-11 | Zoetis Uk Limited | Antiparasitic agents |
| WO2009097972A1 (de) | 2008-02-05 | 2009-08-13 | Sanofi-Aventis | Sf5-derivate als par1-inhibitoren, ihre herstellung und verwendung als arzneimittel |
| US8030512B2 (en) | 2008-10-20 | 2011-10-04 | Ube Industries, Ltd. | Polycyclic pentafluorosulfanylbenzene compound and process for producing the compound |
| US9868701B2 (en) | 2014-12-25 | 2018-01-16 | Ube Industries, Ltd. | Method for producing nitrogen-containing pentafluorosulfanylbenzene compound |
| CN111454186B (zh) * | 2019-01-18 | 2022-11-08 | 山东省联合农药工业有限公司 | 一种含五氟硫基的芳基甲酰苯胺类化合物及其制备方法与用途 |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5045554A (en) * | 1988-11-29 | 1991-09-03 | Monsanto Company | Substituted thiazoles and their use as fungicides |
| US5220070A (en) * | 1991-09-05 | 1993-06-15 | The United States Of America As Represented By The Administrator National Aeronautics And Space Administration | 1,3-diamino-5-pentafluorosulfanylbenzene |
| GB9120641D0 (en) * | 1991-09-27 | 1991-11-06 | Ici Plc | Heterocyclic compounds |
| GB9306184D0 (en) * | 1993-03-25 | 1993-05-19 | Zeneca Ltd | Heteroaromatic compounds |
| GB9306183D0 (en) * | 1993-03-25 | 1993-05-19 | Zeneca Ltd | Novel compounds |
| GB9307245D0 (en) * | 1993-04-07 | 1993-06-02 | Zeneca Ltd | Process |
| AU1430995A (en) * | 1993-12-17 | 1995-07-03 | E.I. Du Pont De Nemours And Company | Arthropodicidal pentafluorothio substituted anilides |
| GB9515599D0 (en) * | 1995-07-29 | 1995-09-27 | British Nuclear Fuels Plc | The preparation of fluorinated organic compounds |
| GB9606015D0 (en) * | 1996-03-22 | 1996-05-22 | Rhone Poulenc Agriculture | New herbicides |
| DE19748109B4 (de) * | 1997-10-31 | 2006-09-07 | Merck Patent Gmbh | Schwefelpentafluorid-Derivate und flüssigkristallines Medium |
| KR20010034302A (ko) * | 1998-01-22 | 2001-04-25 | 한스 루돌프 하우스 | 유기 니트릴 유도체 및 살충제로서의 이의 용도 |
| EP1110454A3 (en) * | 1999-12-16 | 2002-06-05 | Rohm And Haas Company | 5-Carboxanilido-haloalkylthiazoles as antimicrobial and marine antifouling agents |
| CN100354260C (zh) * | 2002-05-02 | 2007-12-12 | 拜尔农作物科学股份公司 | 邻苯二酰胺衍生物、农业或园艺业杀虫剂及其使用方法 |
| JP4389243B2 (ja) * | 2002-05-02 | 2009-12-24 | 日本農薬株式会社 | フタルアミド誘導体及び農園芸用殺虫剤並びにその使用方法 |
| DE10222192A1 (de) * | 2002-05-18 | 2003-11-27 | Aventis Pharma Gmbh | Pentafluorsulfuranyl-benzoylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
| JP2004059452A (ja) * | 2002-07-25 | 2004-02-26 | Asahi Glass Co Ltd | ペンタフルオロサルファー置換ベンズイミダゾール化合物およびその製造方法 |
| JP2004067524A (ja) * | 2002-08-01 | 2004-03-04 | Asahi Glass Co Ltd | ペンタフルオロサルファー置換インドール化合物の製造方法、ペンタフルオロサルファー置換インドール化合物およびその中間体 |
| JP2004067525A (ja) * | 2002-08-01 | 2004-03-04 | Asahi Glass Co Ltd | ペンタフルオロサルファー置換アントラニル酸誘導体の製造方法およびペンタフルオロサルファー置換アントラニル酸誘導体 |
-
2003
- 2003-11-13 DE DE10353205A patent/DE10353205A1/de not_active Withdrawn
-
2004
- 2004-11-03 RU RU2006120474/04A patent/RU2372332C2/ru not_active IP Right Cessation
- 2004-11-03 DK DK04818381.8T patent/DK1685098T3/da active
- 2004-11-03 EP EP04818381A patent/EP1685098B1/de not_active Expired - Lifetime
- 2004-11-03 KR KR1020067009185A patent/KR101165583B1/ko not_active Expired - Fee Related
- 2004-11-03 JP JP2006538731A patent/JP4516968B2/ja not_active Expired - Fee Related
- 2004-11-03 CN CN200480033240A patent/CN100579960C/zh not_active Expired - Fee Related
- 2004-11-03 AU AU2004288759A patent/AU2004288759B2/en not_active Ceased
- 2004-11-03 DE DE502004011054T patent/DE502004011054D1/de not_active Expired - Lifetime
- 2004-11-03 BR BRPI0416031-2A patent/BRPI0416031A/pt active Search and Examination
- 2004-11-03 CA CA2545452A patent/CA2545452C/en not_active Expired - Fee Related
- 2004-11-03 NZ NZ547171A patent/NZ547171A/en not_active IP Right Cessation
- 2004-11-03 WO PCT/EP2004/012394 patent/WO2005047240A1/de not_active Ceased
- 2004-11-03 PT PT04818381T patent/PT1685098E/pt unknown
- 2004-11-03 ES ES04818381T patent/ES2344296T3/es not_active Expired - Lifetime
- 2004-11-03 AT AT04818381T patent/ATE464288T1/de active
- 2004-11-11 AR ARP040104155A patent/AR046619A1/es not_active Application Discontinuation
- 2004-11-11 TW TW093134388A patent/TWI334412B/zh not_active IP Right Cessation
- 2004-11-12 UY UY28615A patent/UY28615A1/es not_active Application Discontinuation
- 2004-11-12 MY MYPI20044736A patent/MY143530A/en unknown
- 2004-11-12 PE PE2004001109A patent/PE20050493A1/es not_active Application Discontinuation
-
2006
- 2006-03-29 ZA ZA200602578A patent/ZA200602578B/en unknown
- 2006-04-26 IL IL175239A patent/IL175239A/en not_active IP Right Cessation
- 2006-05-12 CO CO06045608A patent/CO5690545A2/es active IP Right Grant
- 2006-06-12 NO NO20062701A patent/NO20062701L/no not_active Application Discontinuation
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20171103 |