JP5484795B2 - ２−ベンジル−４−（３，４−ジクロロフェニル）−５−メチルイミダゾール化合物 - Google Patents
２−ベンジル−４−（３，４−ジクロロフェニル）−５−メチルイミダゾール化合物 Download PDFInfo
- Publication number
- JP5484795B2 JP5484795B2 JP2009140655A JP2009140655A JP5484795B2 JP 5484795 B2 JP5484795 B2 JP 5484795B2 JP 2009140655 A JP2009140655 A JP 2009140655A JP 2009140655 A JP2009140655 A JP 2009140655A JP 5484795 B2 JP5484795 B2 JP 5484795B2
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- JP
- Japan
- Prior art keywords
- dichlorophenyl
- methylimidazole
- compound
- hydrochloride
- acetamidine hydrochloride
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- -1 2-Benzyl-4- (3,4-dichlorophenyl) -5-methylimidazole compound Chemical class 0.000 title claims description 27
- 239000000126 substance Substances 0.000 claims description 18
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 150000001875 compounds Chemical class 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 14
- 239000013078 crystal Substances 0.000 description 14
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 14
- 238000000034 method Methods 0.000 description 13
- 238000005160 1H NMR spectroscopy Methods 0.000 description 12
- SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 description 12
- 230000003595 spectral effect Effects 0.000 description 12
- 238000004809 thin layer chromatography Methods 0.000 description 12
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 11
- 229910052802 copper Inorganic materials 0.000 description 11
- 239000010949 copper Substances 0.000 description 11
- 238000012360 testing method Methods 0.000 description 11
- UBSBLGBWNYUPDW-UHFFFAOYSA-N 2-phenylethanimidamide;hydrochloride Chemical compound Cl.NC(=N)CC1=CC=CC=C1 UBSBLGBWNYUPDW-UHFFFAOYSA-N 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 10
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
- 229910000679 solder Inorganic materials 0.000 description 7
- 238000004381 surface treatment Methods 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- FKGDMSJKLIQBQS-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)propan-1-one Chemical class CCC(=O)C1=CC=C(Cl)C(Cl)=C1 FKGDMSJKLIQBQS-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000009736 wetting Methods 0.000 description 4
- YWQFUOSTIJIKRY-UHFFFAOYSA-N 2-(2,4-dichlorophenyl)ethanimidamide;hydrochloride Chemical compound Cl.NC(=N)CC1=CC=C(Cl)C=C1Cl YWQFUOSTIJIKRY-UHFFFAOYSA-N 0.000 description 3
- QKCZDPJRZVWXRC-UHFFFAOYSA-N 2-(2-chlorophenyl)ethanimidamide;hydrochloride Chemical compound Cl.NC(=N)CC1=CC=CC=C1Cl QKCZDPJRZVWXRC-UHFFFAOYSA-N 0.000 description 3
- XHNMUESLGUOKPZ-UHFFFAOYSA-N 2-(3,4-dichlorophenyl)ethanimidamide;hydrochloride Chemical compound Cl.NC(=N)CC1=CC=C(Cl)C(Cl)=C1 XHNMUESLGUOKPZ-UHFFFAOYSA-N 0.000 description 3
- WJPKYOOURIMUTE-UHFFFAOYSA-N 2-(4-bromophenyl)ethanimidamide;hydrochloride Chemical compound Cl.NC(=N)CC1=CC=C(Br)C=C1 WJPKYOOURIMUTE-UHFFFAOYSA-N 0.000 description 3
- JVWYWIOGQGTDGZ-UHFFFAOYSA-N 2-(4-chlorophenyl)ethanimidamide;hydrochloride Chemical compound Cl.NC(=N)CC1=CC=C(Cl)C=C1 JVWYWIOGQGTDGZ-UHFFFAOYSA-N 0.000 description 3
- UXOUDUOPIYYUQG-UHFFFAOYSA-N 2-[(2-chlorophenyl)methyl]-4-(3,4-dichlorophenyl)-5-methyl-1h-imidazole Chemical compound N=1C(C=2C=C(Cl)C(Cl)=CC=2)=C(C)NC=1CC1=CC=CC=C1Cl UXOUDUOPIYYUQG-UHFFFAOYSA-N 0.000 description 3
- ZXRKYCPXQSWHPU-UHFFFAOYSA-N 2-[(4-bromophenyl)methyl]-4-(3,4-dichlorophenyl)-5-methyl-1h-imidazole Chemical compound N=1C(C=2C=C(Cl)C(Cl)=CC=2)=C(C)NC=1CC1=CC=C(Br)C=C1 ZXRKYCPXQSWHPU-UHFFFAOYSA-N 0.000 description 3
- WSKYQZFXOWIGRL-UHFFFAOYSA-N 2-[(4-chlorophenyl)methyl]-4-(3,4-dichlorophenyl)-5-methyl-1h-imidazole Chemical compound N=1C(C=2C=C(Cl)C(Cl)=CC=2)=C(C)NC=1CC1=CC=C(Cl)C=C1 WSKYQZFXOWIGRL-UHFFFAOYSA-N 0.000 description 3
- RGJVGSQPHPDGQG-UHFFFAOYSA-N 2-benzyl-4-(3,4-dichlorophenyl)-5-methyl-1h-imidazole Chemical compound N=1C(C=2C=C(Cl)C(Cl)=CC=2)=C(C)NC=1CC1=CC=CC=C1 RGJVGSQPHPDGQG-UHFFFAOYSA-N 0.000 description 3
- YPKHWACIODYBCI-UHFFFAOYSA-N 2-bromo-1-(3,4-dichlorophenyl)propan-1-one Chemical compound CC(Br)C(=O)C1=CC=C(Cl)C(Cl)=C1 YPKHWACIODYBCI-UHFFFAOYSA-N 0.000 description 3
- QDLGRHSFUUKDFU-UHFFFAOYSA-N 4-(3,4-dichlorophenyl)-2-[(2,4-dichlorophenyl)methyl]-5-methyl-1h-imidazole Chemical compound N=1C(C=2C=C(Cl)C(Cl)=CC=2)=C(C)NC=1CC1=CC=C(Cl)C=C1Cl QDLGRHSFUUKDFU-UHFFFAOYSA-N 0.000 description 3
- SLYXWWFBIJLCSQ-UHFFFAOYSA-N 4-(3,4-dichlorophenyl)-2-[(3,4-dichlorophenyl)methyl]-5-methyl-1h-imidazole Chemical compound N=1C(C=2C=C(Cl)C(Cl)=CC=2)=C(C)NC=1CC1=CC=C(Cl)C(Cl)=C1 SLYXWWFBIJLCSQ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- 230000003078 antioxidant effect Effects 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 229910000881 Cu alloy Inorganic materials 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 239000003905 agrochemical Substances 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000003822 epoxy resin Substances 0.000 description 2
- IWGUPOMJPZNXGC-UHFFFAOYSA-N ethyl 2-phenylethanimidate;hydron;chloride Chemical compound Cl.CCOC(=N)CC1=CC=CC=C1 IWGUPOMJPZNXGC-UHFFFAOYSA-N 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 238000007654 immersion Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 229920000647 polyepoxide Polymers 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 235000011181 potassium carbonates Nutrition 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- SCZNXLWKYFICFV-UHFFFAOYSA-N 1,2,3,4,5,7,8,9-octahydropyrido[1,2-b]diazepine Chemical compound C1CCCNN2CCCC=C21 SCZNXLWKYFICFV-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- RAKVZTFXJRBQKS-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)-2-iodopropan-1-one Chemical compound IC(C(=O)C1=CC(=C(C=C1)Cl)Cl)C RAKVZTFXJRBQKS-UHFFFAOYSA-N 0.000 description 1
- RVULVDCMPNAZQE-UHFFFAOYSA-N 2,2-dichloro-1-phenylpropan-1-one Chemical compound CC(Cl)(Cl)C(=O)C1=CC=CC=C1 RVULVDCMPNAZQE-UHFFFAOYSA-N 0.000 description 1
- HOBXMIAYCXKRIA-UHFFFAOYSA-N 2-(2,3-dibromophenyl)ethanimidamide hydrochloride Chemical compound Cl.BrC1=C(C=CC=C1Br)CC(=N)N HOBXMIAYCXKRIA-UHFFFAOYSA-N 0.000 description 1
- CDGLONLCRQZFNU-UHFFFAOYSA-N 2-(2,3-dichlorophenyl)ethanimidamide;hydrochloride Chemical compound Cl.NC(=N)CC1=CC=CC(Cl)=C1Cl CDGLONLCRQZFNU-UHFFFAOYSA-N 0.000 description 1
- PAEZEIPYDHQJLZ-UHFFFAOYSA-N 2-(2,4-dibromophenyl)ethanimidamide;hydrochloride Chemical compound Cl.NC(=N)CC1=CC=C(Br)C=C1Br PAEZEIPYDHQJLZ-UHFFFAOYSA-N 0.000 description 1
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- ODVSYVSPNHIKQQ-UHFFFAOYSA-N 2-(2,5-dibromophenyl)ethanimidamide hydrochloride Chemical compound Cl.BrC1=C(C=C(C=C1)Br)CC(=N)N ODVSYVSPNHIKQQ-UHFFFAOYSA-N 0.000 description 1
- CTRAOBZMXBESNE-UHFFFAOYSA-N 2-(2,5-dichlorophenyl)ethanimidamide hydrochloride Chemical compound Cl.ClC1=C(C=C(C=C1)Cl)CC(=N)N CTRAOBZMXBESNE-UHFFFAOYSA-N 0.000 description 1
- ZWPGOIGOTBBIJK-UHFFFAOYSA-N 2-(2,6-dibromophenyl)ethanimidamide hydrochloride Chemical compound Cl.BrC1=C(C(=CC=C1)Br)CC(=N)N ZWPGOIGOTBBIJK-UHFFFAOYSA-N 0.000 description 1
- YNPZJFKKDYCULJ-UHFFFAOYSA-N 2-(2,6-dichlorophenyl)ethanimidamide;hydrochloride Chemical compound [Cl-].NC(=[NH2+])CC1=C(Cl)C=CC=C1Cl YNPZJFKKDYCULJ-UHFFFAOYSA-N 0.000 description 1
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- HZUUTZUKLFINGI-UHFFFAOYSA-N 2-(2-bromo-5-chlorophenyl)ethanimidamide hydrochloride Chemical compound Cl.BrC1=C(C=C(C=C1)Cl)CC(=N)N HZUUTZUKLFINGI-UHFFFAOYSA-N 0.000 description 1
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- CVBPFDAWJSDANC-UHFFFAOYSA-N 2-[(3,4-dibromophenyl)methyl]-4-(3,4-dichlorophenyl)-5-methyl-1h-imidazole Chemical compound N=1C(C=2C=C(Cl)C(Cl)=CC=2)=C(C)NC=1CC1=CC=C(Br)C(Br)=C1 CVBPFDAWJSDANC-UHFFFAOYSA-N 0.000 description 1
- VECHXIMJMGYATJ-UHFFFAOYSA-N 2-[(3,5-dibromophenyl)methyl]-4-(3,4-dichlorophenyl)-5-methyl-1h-imidazole Chemical compound N=1C(C=2C=C(Cl)C(Cl)=CC=2)=C(C)NC=1CC1=CC(Br)=CC(Br)=C1 VECHXIMJMGYATJ-UHFFFAOYSA-N 0.000 description 1
- HGBAWSQEYBQLAQ-UHFFFAOYSA-N 2-[(3-bromo-2-chlorophenyl)methyl]-4-(3,4-dichlorophenyl)-5-methyl-1H-imidazole Chemical compound BrC=1C(=C(CC=2NC(=C(N=2)C2=CC(=C(C=C2)Cl)Cl)C)C=CC=1)Cl HGBAWSQEYBQLAQ-UHFFFAOYSA-N 0.000 description 1
- VEVGSDLTNOLVHO-UHFFFAOYSA-N 2-[(3-bromo-4-chlorophenyl)methyl]-4-(3,4-dichlorophenyl)-5-methyl-1h-imidazole Chemical compound N=1C(C=2C=C(Cl)C(Cl)=CC=2)=C(C)NC=1CC1=CC=C(Cl)C(Br)=C1 VEVGSDLTNOLVHO-UHFFFAOYSA-N 0.000 description 1
- ZWVMTKCJKPMDSO-UHFFFAOYSA-N 2-[(3-bromo-5-chlorophenyl)methyl]-4-(3,4-dichlorophenyl)-5-methyl-1h-imidazole Chemical compound N=1C(C=2C=C(Cl)C(Cl)=CC=2)=C(C)NC=1CC1=CC(Cl)=CC(Br)=C1 ZWVMTKCJKPMDSO-UHFFFAOYSA-N 0.000 description 1
- DYIOSDKKUVJZEE-UHFFFAOYSA-N 2-[(3-bromophenyl)methyl]-4-(3,4-dichlorophenyl)-5-methyl-1h-imidazole Chemical compound N=1C(C=2C=C(Cl)C(Cl)=CC=2)=C(C)NC=1CC1=CC=CC(Br)=C1 DYIOSDKKUVJZEE-UHFFFAOYSA-N 0.000 description 1
- LOFWTEWOPVUDPR-UHFFFAOYSA-N 2-[(3-chlorophenyl)methyl]-4-(3,4-dichlorophenyl)-5-methyl-1h-imidazole Chemical compound N=1C(C=2C=C(Cl)C(Cl)=CC=2)=C(C)NC=1CC1=CC=CC(Cl)=C1 LOFWTEWOPVUDPR-UHFFFAOYSA-N 0.000 description 1
- PODRNLUUOYUUGD-UHFFFAOYSA-N 2-[(4-bromo-2-chlorophenyl)methyl]-4-(3,4-dichlorophenyl)-5-methyl-1h-imidazole Chemical compound N=1C(C=2C=C(Cl)C(Cl)=CC=2)=C(C)NC=1CC1=CC=C(Br)C=C1Cl PODRNLUUOYUUGD-UHFFFAOYSA-N 0.000 description 1
- VZBBRRUXORZSMY-UHFFFAOYSA-N 2-[(4-bromo-3-chlorophenyl)methyl]-4-(3,4-dichlorophenyl)-5-methyl-1h-imidazole Chemical compound N=1C(C=2C=C(Cl)C(Cl)=CC=2)=C(C)NC=1CC1=CC=C(Br)C(Cl)=C1 VZBBRRUXORZSMY-UHFFFAOYSA-N 0.000 description 1
- IZSQQADSZALATF-UHFFFAOYSA-N 2-[(5-bromo-2-chlorophenyl)methyl]-4-(3,4-dichlorophenyl)-5-methyl-1h-imidazole Chemical compound N=1C(C=2C=C(Cl)C(Cl)=CC=2)=C(C)NC=1CC1=CC(Br)=CC=C1Cl IZSQQADSZALATF-UHFFFAOYSA-N 0.000 description 1
- XLSUKENQJDZSCX-UHFFFAOYSA-N 2-chloro-1-(3,4-dichlorophenyl)propan-1-one Chemical compound CC(Cl)C(=O)C1=CC=C(Cl)C(Cl)=C1 XLSUKENQJDZSCX-UHFFFAOYSA-N 0.000 description 1
- ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 2-phenyl-1h-imidazole Chemical compound C1=CNC(C=2C=CC=CC=2)=N1 ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 0.000 description 1
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 1
- JZLREMYLVMQEFD-UHFFFAOYSA-N 4-(3,4-dichlorophenyl)-2-[(2,3-dichlorophenyl)methyl]-5-methyl-1h-imidazole Chemical compound N=1C(C=2C=C(Cl)C(Cl)=CC=2)=C(C)NC=1CC1=CC=CC(Cl)=C1Cl JZLREMYLVMQEFD-UHFFFAOYSA-N 0.000 description 1
- FETDXYBEJAFREO-UHFFFAOYSA-N 4-(3,4-dichlorophenyl)-2-[(2,5-dichlorophenyl)methyl]-5-methyl-1h-imidazole Chemical compound N=1C(C=2C=C(Cl)C(Cl)=CC=2)=C(C)NC=1CC1=CC(Cl)=CC=C1Cl FETDXYBEJAFREO-UHFFFAOYSA-N 0.000 description 1
- HQZUQQNUEHABQK-UHFFFAOYSA-N 4-(3,4-dichlorophenyl)-2-[(2,6-dichlorophenyl)methyl]-5-methyl-1H-imidazole Chemical compound ClC1=C(CC=2NC(=C(N=2)C2=CC(=C(C=C2)Cl)Cl)C)C(=CC=C1)Cl HQZUQQNUEHABQK-UHFFFAOYSA-N 0.000 description 1
- PTRXJGGECKSLMO-UHFFFAOYSA-N 4-(3,4-dichlorophenyl)-2-[(3,5-dichlorophenyl)methyl]-5-methyl-1h-imidazole Chemical compound N=1C(C=2C=C(Cl)C(Cl)=CC=2)=C(C)NC=1CC1=CC(Cl)=CC(Cl)=C1 PTRXJGGECKSLMO-UHFFFAOYSA-N 0.000 description 1
- IVYMIRMKXZAHRV-UHFFFAOYSA-N 4-chlorophenylacetonitrile Chemical compound ClC1=CC=C(CC#N)C=C1 IVYMIRMKXZAHRV-UHFFFAOYSA-N 0.000 description 1
- QEKMZWLVMAITDK-UHFFFAOYSA-N 5-(3,4-dichlorophenyl)-2-[(2,4-dichlorophenyl)methyl]-1h-imidazole Chemical compound ClC1=CC(Cl)=CC=C1CC1=NC=C(C=2C=C(Cl)C(Cl)=CC=2)N1 QEKMZWLVMAITDK-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 0 C*(C(N(C)C1=CC=CCC1)=*1)C(NC=C=C)=C1c(cc1C)ccc1N Chemical compound C*(C(N(C)C1=CC=CCC1)=*1)C(NC=C=C)=C1c(cc1C)ccc1N 0.000 description 1
- 102220474387 PDZ and LIM domain protein 7_H63A_mutation Human genes 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 230000003064 anti-oxidating effect Effects 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 235000011116 calcium hydroxide Nutrition 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- WCQOBLXWLRDEQA-UHFFFAOYSA-N ethanimidamide;hydrochloride Chemical compound Cl.CC(N)=N WCQOBLXWLRDEQA-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 230000005496 eutectics Effects 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 150000002366 halogen compounds Chemical class 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 230000026045 iodination Effects 0.000 description 1
- 238000006192 iodination reaction Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- LQBJWKCYZGMFEV-UHFFFAOYSA-N lead tin Chemical compound [Sn].[Pb] LQBJWKCYZGMFEV-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000013519 translation Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
- C23F—NON-MECHANICAL REMOVAL OF METALLIC MATERIAL FROM SURFACE; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL; MULTI-STEP PROCESSES FOR SURFACE TREATMENT OF METALLIC MATERIAL INVOLVING AT LEAST ONE PROCESS PROVIDED FOR IN CLASS C23 AND AT LEAST ONE PROCESS COVERED BY SUBCLASS C21D OR C22F OR CLASS C25
- C23F11/00—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent
- C23F11/08—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids
- C23F11/10—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids using organic inhibitors
- C23F11/14—Nitrogen-containing compounds
- C23F11/149—Heterocyclic compounds containing nitrogen as hetero atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B23—MACHINE TOOLS; METAL-WORKING NOT OTHERWISE PROVIDED FOR
- B23K—SOLDERING OR UNSOLDERING; WELDING; CLADDING OR PLATING BY SOLDERING OR WELDING; CUTTING BY APPLYING HEAT LOCALLY, e.g. FLAME CUTTING; WORKING BY LASER BEAM
- B23K1/00—Soldering, e.g. brazing, or unsoldering
- B23K1/20—Preliminary treatment of work or areas to be soldered, e.g. in respect of a galvanic coating
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B23—MACHINE TOOLS; METAL-WORKING NOT OTHERWISE PROVIDED FOR
- B23K—SOLDERING OR UNSOLDERING; WELDING; CLADDING OR PLATING BY SOLDERING OR WELDING; CUTTING BY APPLYING HEAT LOCALLY, e.g. FLAME CUTTING; WORKING BY LASER BEAM
- B23K35/00—Rods, electrodes, materials, or media, for use in soldering, welding, or cutting
- B23K35/22—Rods, electrodes, materials, or media, for use in soldering, welding, or cutting characterised by the composition or nature of the material
- B23K35/36—Selection of non-metallic compositions, e.g. coatings, fluxes; Selection of soldering or welding materials, conjoint with selection of non-metallic compositions, both selections being of interest
- B23K35/3612—Selection of non-metallic compositions, e.g. coatings, fluxes; Selection of soldering or welding materials, conjoint with selection of non-metallic compositions, both selections being of interest with organic compounds as principal constituents
- B23K35/3615—N-compounds
-
- C—CHEMISTRY; METALLURGY
- C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
- C23C—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; SURFACE TREATMENT OF METALLIC MATERIAL BY DIFFUSION INTO THE SURFACE, BY CHEMICAL CONVERSION OR SUBSTITUTION; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL
- C23C22/00—Chemical surface treatment of metallic material by reaction of the surface with a reactive liquid, leaving reaction products of surface material in the coating, e.g. conversion coatings, passivation of metals
- C23C22/05—Chemical surface treatment of metallic material by reaction of the surface with a reactive liquid, leaving reaction products of surface material in the coating, e.g. conversion coatings, passivation of metals using aqueous solutions
- C23C22/06—Chemical surface treatment of metallic material by reaction of the surface with a reactive liquid, leaving reaction products of surface material in the coating, e.g. conversion coatings, passivation of metals using aqueous solutions using aqueous acidic solutions with pH less than 6
- C23C22/48—Chemical surface treatment of metallic material by reaction of the surface with a reactive liquid, leaving reaction products of surface material in the coating, e.g. conversion coatings, passivation of metals using aqueous solutions using aqueous acidic solutions with pH less than 6 not containing phosphates, hexavalent chromium compounds, fluorides or complex fluorides, molybdates, tungstates, vanadates or oxalates
- C23C22/52—Treatment of copper or alloys based thereon
-
- C—CHEMISTRY; METALLURGY
- C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
- C23F—NON-MECHANICAL REMOVAL OF METALLIC MATERIAL FROM SURFACE; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL; MULTI-STEP PROCESSES FOR SURFACE TREATMENT OF METALLIC MATERIAL INVOLVING AT LEAST ONE PROCESS PROVIDED FOR IN CLASS C23 AND AT LEAST ONE PROCESS COVERED BY SUBCLASS C21D OR C22F OR CLASS C25
- C23F11/00—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent
- C23F11/08—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids
- C23F11/10—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids using organic inhibitors
- C23F11/14—Nitrogen-containing compounds
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K3/00—Apparatus or processes for manufacturing printed circuits
- H05K3/22—Secondary treatment of printed circuits
- H05K3/28—Applying non-metallic protective coatings
- H05K3/282—Applying non-metallic protective coatings for inhibiting the corrosion of the circuit, e.g. for preserving the solderability
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Mechanical Engineering (AREA)
- Engineering & Computer Science (AREA)
- Metallurgy (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Chemical Treatment Of Metals (AREA)
- Preventing Corrosion Or Incrustation Of Metals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2009140655A JP5484795B2 (ja) | 2008-09-03 | 2009-06-12 | ２−ベンジル−４−（３，４−ジクロロフェニル）−５−メチルイミダゾール化合物 |
| PCT/JP2009/065616 WO2010027077A1 (fr) | 2008-09-03 | 2009-09-02 | Composé de 2-benzyl-4-(3,4-dichlorophényl)-5-méthylimidazole |
| CN200980134515.8A CN102144046B (zh) | 2008-09-03 | 2009-09-02 | 2-苯甲基-4-(3，4-二氯苯基)-5-甲基咪唑化合物 |
| KR1020117005121A KR101602978B1 (ko) | 2008-09-03 | 2009-09-02 | 2-벤질-4-(3,4-디클로로페닐)-5-메틸이미다졸 화합물 |
| MYPI2011000846A MY158638A (en) | 2008-09-03 | 2009-09-02 | 2-benzly-4-(3,4-dichlorophenyl)-5-methylimidazole compound |
| TW098129659A TWI507395B (zh) | 2008-09-03 | 2009-09-03 | ２－苄基－４－（３，４－二氯苯基）－５－甲基咪唑化合物及其衍生物 |
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2008225632 | 2008-09-03 | ||
| JP2008225632 | 2008-09-03 | ||
| JP2009130022 | 2009-05-29 | ||
| JP2009130022 | 2009-05-29 | ||
| JP2009140655A JP5484795B2 (ja) | 2008-09-03 | 2009-06-12 | ２−ベンジル−４−（３，４−ジクロロフェニル）−５−メチルイミダゾール化合物 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2011006323A JP2011006323A (ja) | 2011-01-13 |
| JP5484795B2 true JP5484795B2 (ja) | 2014-05-07 |
Family
ID=41323603
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009140655A Active JP5484795B2 (ja) | 2008-09-03 | 2009-06-12 | ２−ベンジル−４−（３，４−ジクロロフェニル）−５−メチルイミダゾール化合物 |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JP5484795B2 (fr) |
| KR (1) | KR101602978B1 (fr) |
| CN (1) | CN102144046B (fr) |
| MY (1) | MY158638A (fr) |
| TW (1) | TWI507395B (fr) |
| WO (1) | WO2010027077A1 (fr) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5260208B2 (ja) * | 2008-09-22 | 2013-08-14 | 四国化成工業株式会社 | ２−（２，４−ジクロロベンジル）−４−（ハロゲン化フェニル）イミダゾール化合物 |
| JP5260367B2 (ja) * | 2008-09-26 | 2013-08-14 | 四国化成工業株式会社 | ２−（クロロベンジル）−４−フェニルイミダゾール化合物 |
| JP5615227B2 (ja) * | 2011-05-23 | 2014-10-29 | 四国化成工業株式会社 | 銅または銅合金の表面処理剤及びその利用 |
| JP5615233B2 (ja) * | 2011-06-20 | 2014-10-29 | 四国化成工業株式会社 | 銅または銅合金の表面処理剤及びその利用 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW270944B (fr) * | 1993-05-10 | 1996-02-21 | Shikoku Kakoki Co Ltd | |
| JP3277025B2 (ja) * | 1993-05-10 | 2002-04-22 | 四国化成工業株式会社 | 銅及び銅合金の表面処理剤 |
| JPH06329635A (ja) * | 1993-05-24 | 1994-11-29 | Shikoku Chem Corp | 新規イミダゾール化合物 |
| JP3311858B2 (ja) * | 1994-03-08 | 2002-08-05 | 四国化成工業株式会社 | 銅及び銅合金の表面処理剤 |
| AR024077A1 (es) * | 1999-05-25 | 2002-09-04 | Smithkline Beecham Corp | Compuestos antibacterianos |
| ATE474944T1 (de) * | 2003-03-19 | 2010-08-15 | Shikoku Chem | Lötverfahren unter verwendung einer imidazolverbindung |
-
2009
- 2009-06-12 JP JP2009140655A patent/JP5484795B2/ja active Active
- 2009-09-02 KR KR1020117005121A patent/KR101602978B1/ko active IP Right Grant
- 2009-09-02 WO PCT/JP2009/065616 patent/WO2010027077A1/fr active Application Filing
- 2009-09-02 MY MYPI2011000846A patent/MY158638A/en unknown
- 2009-09-02 CN CN200980134515.8A patent/CN102144046B/zh active Active
- 2009-09-03 TW TW098129659A patent/TWI507395B/zh active
Also Published As
| Publication number | Publication date |
|---|---|
| CN102144046A (zh) | 2011-08-03 |
| KR20110050663A (ko) | 2011-05-16 |
| CN102144046B (zh) | 2014-02-26 |
| TWI507395B (zh) | 2015-11-11 |
| MY158638A (en) | 2016-10-31 |
| TW201010982A (en) | 2010-03-16 |
| KR101602978B1 (ko) | 2016-03-11 |
| WO2010027077A1 (fr) | 2010-03-11 |
| JP2011006323A (ja) | 2011-01-13 |
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