JP2014037380A - 4-(2-thienyl)imidazole compound - Google Patents
4-(2-thienyl)imidazole compound Download PDFInfo
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- JP2014037380A JP2014037380A JP2012180748A JP2012180748A JP2014037380A JP 2014037380 A JP2014037380 A JP 2014037380A JP 2012180748 A JP2012180748 A JP 2012180748A JP 2012180748 A JP2012180748 A JP 2012180748A JP 2014037380 A JP2014037380 A JP 2014037380A
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- Prior art keywords
- thienyl
- compound
- imidazole
- imidazole compound
- thiophene
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- -1 4-(2-thienyl)imidazole compound Chemical class 0.000 title claims abstract description 36
- 239000000126 substance Substances 0.000 claims description 11
- 239000003795 chemical substances by application Substances 0.000 abstract description 7
- 239000003960 organic solvent Substances 0.000 abstract description 5
- 150000001875 compounds Chemical class 0.000 abstract description 3
- 238000006704 dehydrohalogenation reaction Methods 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
- 238000006243 chemical reaction Methods 0.000 description 14
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 12
- 229910052802 copper Inorganic materials 0.000 description 12
- 239000010949 copper Substances 0.000 description 12
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- 239000003963 antioxidant agent Substances 0.000 description 9
- 230000003078 antioxidant effect Effects 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 239000000843 powder Substances 0.000 description 9
- 239000013078 crystal Substances 0.000 description 8
- 229910000679 solder Inorganic materials 0.000 description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical class ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- ISEXQXDJGISUKO-UHFFFAOYSA-N 2-bromo-1-thiophen-2-ylpropan-1-one Chemical compound CC(Br)C(=O)C1=CC=CS1 ISEXQXDJGISUKO-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 238000004809 thin layer chromatography Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- WYJOVVXUZNRJQY-UHFFFAOYSA-N 2-Acetylthiophene Chemical compound CC(=O)C1=CC=CS1 WYJOVVXUZNRJQY-UHFFFAOYSA-N 0.000 description 4
- CMHXKIGMNOSJSH-UHFFFAOYSA-N 2-[(2,4-dichlorophenyl)methyl]-5-thiophen-2-yl-1h-imidazole Chemical compound ClC1=CC(Cl)=CC=C1CC1=NC=C(C=2SC=CC=2)N1 CMHXKIGMNOSJSH-UHFFFAOYSA-N 0.000 description 4
- DVPQHUVCBCMUMH-UHFFFAOYSA-N 5-methyl-2-phenyl-4-thiophen-2-yl-1h-imidazole Chemical compound CC=1NC(C=2C=CC=CC=2)=NC=1C1=CC=CS1 DVPQHUVCBCMUMH-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
- LZCZIHQBSCVGRD-UHFFFAOYSA-N benzenecarboximidamide;hydron;chloride Chemical compound [Cl-].NC(=[NH2+])C1=CC=CC=C1 LZCZIHQBSCVGRD-UHFFFAOYSA-N 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal 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
- MFPZQZZWAMAHOY-UHFFFAOYSA-N 2-Propanoylthiophene Chemical compound CCC(=O)C1=CC=CS1 MFPZQZZWAMAHOY-UHFFFAOYSA-N 0.000 description 3
- UHWNENCHFSDZQP-UHFFFAOYSA-N 2-bromo-1-thiophen-2-ylethanone Chemical compound BrCC(=O)C1=CC=CS1 UHWNENCHFSDZQP-UHFFFAOYSA-N 0.000 description 3
- XWFNTKZZLRQHTR-UHFFFAOYSA-N 5-methyl-2,4-dithiophen-2-yl-1h-imidazole Chemical compound CC=1NC(C=2SC=CC=2)=NC=1C1=CC=CS1 XWFNTKZZLRQHTR-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-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
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 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
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 230000003595 spectral effect Effects 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- CUPOOAWTRIURFT-UHFFFAOYSA-N thiophene-2-carbonitrile Chemical compound N#CC1=CC=CS1 CUPOOAWTRIURFT-UHFFFAOYSA-N 0.000 description 3
- URAGJMBGNVOIJC-UHFFFAOYSA-N thiophene-2-carboximidamide;hydrochloride Chemical compound Cl.NC(=N)C1=CC=CS1 URAGJMBGNVOIJC-UHFFFAOYSA-N 0.000 description 3
- 238000009736 wetting Methods 0.000 description 3
- 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 2
- PWKJMPFEQOHBAC-UHFFFAOYSA-N 4-Ethyloctanoic acid Chemical compound CCCCC(CC)CCC(O)=O PWKJMPFEQOHBAC-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 229910000881 Cu alloy Inorganic materials 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
- 150000001408 amides Chemical class 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 239000012267 brine Substances 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
- 239000003814 drug Substances 0.000 description 2
- 239000003822 epoxy resin Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 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 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000007654 immersion Methods 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 150000002739 metals Chemical class 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
- 238000002360 preparation method Methods 0.000 description 2
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000004381 surface treatment Methods 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
- HUKFRPZKURKTQB-UHFFFAOYSA-N 2-(2,4-dichlorophenyl)ethanimidamide Chemical compound NC(=N)CC1=CC=C(Cl)C=C1Cl HUKFRPZKURKTQB-UHFFFAOYSA-N 0.000 description 1
- VDUYWIUPWHTFFE-UHFFFAOYSA-N 2-[(2,4-dichlorophenyl)methyl]-5-methyl-4-thiophen-2-yl-1h-imidazole Chemical compound N=1C(C=2SC=CC=2)=C(C)NC=1CC1=CC=C(Cl)C=C1Cl VDUYWIUPWHTFFE-UHFFFAOYSA-N 0.000 description 1
- KHOWLHQEABZKNA-UHFFFAOYSA-N 2-chloro-1-thiophen-2-ylethanone Chemical compound ClCC(=O)C1=CC=CS1 KHOWLHQEABZKNA-UHFFFAOYSA-N 0.000 description 1
- YBJIAOWXOCYNOV-UHFFFAOYSA-N 2-chloro-1-thiophen-2-ylpropan-1-one Chemical compound CC(Cl)C(=O)C1=CC=CS1 YBJIAOWXOCYNOV-UHFFFAOYSA-N 0.000 description 1
- OZRPZICEGUYQTI-UHFFFAOYSA-N 2-iodo-1-thiophen-2-ylethanone Chemical compound ICC(=O)C1=CC=CS1 OZRPZICEGUYQTI-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
- FCLYMCAZNWGPKQ-UHFFFAOYSA-N 2-phenyl-5-thiophen-2-yl-1h-imidazole Chemical compound C1=CSC(C=2NC(=NC=2)C=2C=CC=CC=2)=C1 FCLYMCAZNWGPKQ-UHFFFAOYSA-N 0.000 description 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 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
- VBEGGQMCRARLJH-UHFFFAOYSA-N CC(C(=O)C1=CC=CS1)I Chemical compound CC(C(=O)C1=CC=CS1)I VBEGGQMCRARLJH-UHFFFAOYSA-N 0.000 description 1
- 235000006040 Prunus persica var persica Nutrition 0.000 description 1
- 240000006413 Prunus persica var. persica Species 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- PXXJHWLDUBFPOL-UHFFFAOYSA-N benzamidine Chemical compound NC(=N)C1=CC=CC=C1 PXXJHWLDUBFPOL-UHFFFAOYSA-N 0.000 description 1
- 230000031709 bromination Effects 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
- 238000005660 chlorination reaction Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- CEIPQQODRKXDSB-UHFFFAOYSA-N ethyl 3-(6-hydroxynaphthalen-2-yl)-1H-indazole-5-carboximidate dihydrochloride Chemical compound Cl.Cl.C1=C(O)C=CC2=CC(C3=NNC4=CC=C(C=C43)C(=N)OCC)=CC=C21 CEIPQQODRKXDSB-UHFFFAOYSA-N 0.000 description 1
- 230000005496 eutectics Effects 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000007789 gas 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
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 239000003112 inhibitor Substances 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
- 239000000463 material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
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- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
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Landscapes
- Anti-Oxidant Or Stabilizer Compositions (AREA)
- Epoxy Resins (AREA)
- Chemical Treatment Of Metals (AREA)
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Abstract
Description
本発明は、新規な4−(2−チエニル)イミダゾール化合物に関するものである。 The present invention relates to a novel 4- (2-thienyl) imidazole compound.
本発明に類似のイミダゾール化合物として、例えば、非特許文献1及び非特許文献2には、化学式(III)で示される2−フェニル−4−(2−チエニル)イミダゾールが開示されている。しかしながら、これらの文献には本発明のイミダゾール化合物の開示はない。 As an imidazole compound similar to the present invention, for example, Non-Patent Document 1 and Non-Patent Document 2 disclose 2-phenyl-4- (2-thienyl) imidazole represented by the chemical formula (III). However, these documents do not disclose the imidazole compound of the present invention.
本発明は、新規な4−(2−チエニル)イミダゾール化合物を提供することを目的とする。 An object of the present invention is to provide a novel 4- (2-thienyl) imidazole compound.
本発明者等は、前記の課題を解決するために鋭意検討を重ねた結果、化学式(I)又は化学式(II)で示される新規な4−(2−チエニル)イミダゾール化合物を合成し得ることを認め、本発明を完成するに至ったものである。当該イミダゾール化合物は、2−チエニル基がイミダゾール環の4位に結合している。 As a result of intensive studies to solve the above-mentioned problems, the present inventors have been able to synthesize a novel 4- (2-thienyl) imidazole compound represented by the chemical formula (I) or the chemical formula (II). Acknowledgment has led to the completion of the present invention. In the imidazole compound, the 2-thienyl group is bonded to the 4-position of the imidazole ring.
本発明の4−(2−チエニル)イミダゾール化合物は、金属、特に銅(銅合金を含む)の表面の酸化防止剤や、エポキシ樹脂の硬化剤又は硬化促進剤として、また医農薬分野の中間原料としても有用なものである。 The 4- (2-thienyl) imidazole compound of the present invention is used as an antioxidant on the surface of metals, particularly copper (including copper alloys), as a curing agent or curing accelerator for epoxy resins, and as an intermediate raw material in the field of medicine and agrochemicals. It is also useful.
以下、本発明について詳細に説明する。
本発明の4−(2−チエニル)イミダゾール化合物は、
5−メチル−2−フェニル−4−(2−チエニル)イミダゾール、
5−メチル−2,4−ジ(2−チエニル)イミダゾール、
2−(2,4−ジクロロベンジル)−5−メチル−4−(2−チエニル)イミダゾール及び
2−(2,4−ジクロロベンジル)−4−(2−チエニル)イミダゾールである。
Hereinafter, the present invention will be described in detail.
The 4- (2-thienyl) imidazole compound of the present invention is
5-methyl-2-phenyl-4- (2-thienyl) imidazole,
5-methyl-2,4-di (2-thienyl) imidazole,
2- (2,4-dichlorobenzyl) -5-methyl-4- (2-thienyl) imidazole and 2- (2,4-dichlorobenzyl) -4- (2-thienyl) imidazole.
本発明の4−(2−チエニル)イミダゾール化合物は、公知の方法に準拠して合成することができる。例えば、反応式(A)に示されるように、2位ハロゲン化アルキル−2−チエニルケトン化合物及びアミジン化合物を脱ハロゲン化水素剤の存在下、有機溶媒中で加熱反応をさせることにより合成することができる。 The 4- (2-thienyl) imidazole compound of the present invention can be synthesized according to a known method. For example, as shown in the reaction formula (A), a 2-position halogenated alkyl-2-thienyl ketone compound and an amidine compound are synthesized by heating in an organic solvent in the presence of a dehydrohalogenating agent. Can do.
前述の反応において、アミジン化合物の使用量は、2位ハロゲン化アルキル−2−チエニルケトン化合物に対して、0.8〜1.5倍モルが好ましく、より好ましくは0.9〜1.1倍モルの割合とすればよい。脱ハロゲン化水素剤の使用量は、2位ハロゲン化アルキル−2−チエニルケトン化合物に対して、1〜10倍当量の割合が好ましい。 In the above reaction, the amount of the amidine compound used is preferably 0.8 to 1.5 times, more preferably 0.9 to 1.1 times the mol of the 2-position halogenated alkyl-2-thienyl ketone compound. A mole ratio may be used. The amount of the dehydrohalogenating agent used is preferably a ratio of 1 to 10 equivalents with respect to the 2-position halogenated alkyl-2-thienyl ketone compound.
前記の2位ハロゲン化アルキル−2−チエニルケトン化合物としては、2−(2−クロロアセチル)チオフェン、2−(2−ブロモアセチル)チオフェン、2−(2−ヨードアセチル)チオフェン、2−(2−クロロプロピオニル)チオフェン、2−(2−ブロモプロピオニル)チオフェン及び2−(2−ヨードプロピオニル)チオフェンが挙げられる。 Examples of the 2-position halogenated alkyl-2-thienyl ketone compound include 2- (2-chloroacetyl) thiophene, 2- (2-bromoacetyl) thiophene, 2- (2-iodoacetyl) thiophene, 2- (2 -Chloropropionyl) thiophene, 2- (2-bromopropionyl) thiophene and 2- (2-iodopropionyl) thiophene.
これらの2位ハロゲン化アルキル−2−チエニルケトン化合物は、アルキル−2−チエニルケトン化合物の2位をハロゲン化することにより合成することができる。2位ハロゲン化の内、2位塩素化及び2位ヨウ素化も可能であるが、アルキル−2−チエニルケトン化合物1モルに対し、1モルの臭素を反応させる2位臭素化が最も簡便である。 These 2-position halogenated alkyl-2-thienyl ketone compounds can be synthesized by halogenating the 2-position of the alkyl-2-thienyl ketone compound. Among the 2-position halogenations, 2-position chlorination and 2-position iodination are possible, but 2-position bromination in which 1 mole of bromine is reacted with 1 mole of alkyl-2-thienyl ketone compound is the simplest. .
前記のアルキル−2−チエニルケトン化合物としては、2−アセチルチオフェン及び2−プロピオニルチオフェンが挙げられる。これらは公知の化合物であり、試薬として市販されているものを使用することができる。 Examples of the alkyl-2-thienyl ketone compound include 2-acetylthiophene and 2-propionylthiophene. These are known compounds, and those commercially available as reagents can be used.
前記のアミジン化合物は、公知の方法に準拠して合成することができる。すなわち、反応式(B)に示されるように、前駆体のニトリル化合物を塩化水素ガス及びエタノール等の低級アルコールと反応させ、イミデート・塩酸塩化合物に変換し、更にアンモニアと反応させることによってアミジン化合物を合成することができる。 The amidine compound can be synthesized according to a known method. That is, as shown in the reaction formula (B), the precursor nitrile compound is reacted with a lower alcohol such as hydrogen chloride gas and ethanol, converted into an imidate / hydrochloride compound, and further reacted with ammonia to form an amidine compound. Can be synthesized.
前記のアミジン化合物としては、ベンズアミジン、2−チオフェンカルボキシミドアミド、(2,4−ジクロロフェニル)アセトアミジン及びこれらの塩酸塩等の無機酸塩や酢酸塩等の有機酸塩が挙げられる。これらのうち、ベンズアミジン塩酸塩は試薬として市販されているものを使用することができる。 Examples of the amidine compound include benzamidine, 2-thiophenecarboximidamide, (2,4-dichlorophenyl) acetamidine, and organic acid salts such as acetates and inorganic acid salts such as hydrochlorides thereof. Of these, benzamidine hydrochloride may be one that is commercially available as a reagent.
前記のニトリル化合物としては、ベンゾニトリル、2−シアノチオフェン及び2,4−ジクロロベンジルシアニドが挙げられる。これらは公知の化合物であり、試薬として市販されているものを使用することができる。 Examples of the nitrile compound include benzonitrile, 2-cyanothiophene, and 2,4-dichlorobenzyl cyanide. These are known compounds, and those commercially available as reagents can be used.
前記の脱ハロゲン化水素剤は公知のものを制限なく使用できる。このような脱ハロゲン化水素剤としては、例えば、水酸化ナトリウム、水酸化カリウム、水酸化カルシウム、炭酸ナトリウム、炭酸カリウム、重炭酸ナトリウム、重炭酸カリウムのような無機アルカリ類、トリエチルアミン、1,8−ジアザビシクロ[5,4,0]−7−ウンデセン(DBU)のような有機塩基類、ナトリウムメトキシド、カリウムtert−ブトキシドのような金属アルコキシド類等が挙げられる。 Any known dehydrohalogenating agent can be used without limitation. Examples of such a dehydrohalogenating agent include inorganic alkalis such as sodium hydroxide, potassium hydroxide, calcium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, triethylamine, 1,8 -Organic bases such as diazabicyclo [5,4,0] -7-undecene (DBU), metal alkoxides such as sodium methoxide and potassium tert-butoxide, and the like.
前記の有機溶媒は、2位ハロゲン化アルキル−2−チエニルケトン化合物及びアミジン化合物を溶解することができ、かつ反応に関与しないものであれば公知のものを制限なく使用できる。このような溶媒として、例えば、イソプロピルアルコール、tert−ブタノールなどのアルコール類、ヘキサン、トルエンなどの炭化水素類、クロロホルム、クロロベンゼンなどのハロゲン化炭化水素類、酢酸エチルなどのエステル類、アセトニトリルなどのニトリル類、テトラヒドロフラン、ジオキサン、エチレングリコールジメチルエーテルなどのエーテル類、N,N−ジメチルホルムアミド(DMF)、N,N−ジメチルアセトアミド(DMAC)などのアミド類、ジメチルスルホキシド(DMSO)等が挙げられ、これらの溶媒を組み合わせて使用してもよい。 Any known organic solvent can be used without limitation as long as it can dissolve the 2-position halogenated alkyl-2-thienyl ketone compound and amidine compound and does not participate in the reaction. Examples of such solvents include alcohols such as isopropyl alcohol and tert-butanol, hydrocarbons such as hexane and toluene, halogenated hydrocarbons such as chloroform and chlorobenzene, esters such as ethyl acetate, and nitriles such as acetonitrile. , Ethers such as tetrahydrofuran, dioxane, ethylene glycol dimethyl ether, amides such as N, N-dimethylformamide (DMF), N, N-dimethylacetamide (DMAC), dimethyl sulfoxide (DMSO), and the like. A combination of solvents may be used.
反応温度については、室温〜還流温度とすることが好ましく、反応時間については、1〜10時間とすることが好ましい。反応は、通常大気圧下で行えばよい。 The reaction temperature is preferably room temperature to reflux temperature, and the reaction time is preferably 1 to 10 hours. The reaction may be usually performed under atmospheric pressure.
以上の反応条件下で生成した4−(2−チエニル)イミダゾール化合物は、通常の後処理によって単離することができる。
例えば、反応終了後の反応混合物を水層と有機溶媒層に分配し、有機溶媒層を水で洗浄することにより結晶として析出する粗製の4−(2−チエニル)イミダゾール化合物を得ることができ、それを再結晶操作等により精製することができる。
The 4- (2-thienyl) imidazole compound produced under the above reaction conditions can be isolated by ordinary post-treatment.
For example, the reaction mixture after completion of the reaction is divided into an aqueous layer and an organic solvent layer, and a crude 4- (2-thienyl) imidazole compound that precipitates as crystals can be obtained by washing the organic solvent layer with water. It can be purified by a recrystallization operation or the like.
以下、本発明を実施例によって具体的に説明するが、本発明はこれらに限定されるものではない。なお、2−(2−ブロモプロピオニル)チオフェン及び2−チオフェンカルボキシミドアミド塩酸塩の合成例を、参考例1及び2に示す。 EXAMPLES Hereinafter, the present invention will be specifically described with reference to examples, but the present invention is not limited to these examples. Reference examples 1 and 2 show synthesis examples of 2- (2-bromopropionyl) thiophene and 2-thiophenecarboximidamide hydrochloride.
〔参考例1〕
<2−(2−ブロモプロピオニル)チオフェン/トルエン溶液の調製>
2−プロピオニルチオフェン25.2g(0.180mol)及びメタノール29gからなる溶液に、30〜35℃にて、臭素28.7g(0.180mol)を30分かけて滴下した。次いで、反応液を冷却後、濃縮物が43gになるまで減圧濃縮した。濃縮物をトルエン80ml及び食塩水80mlに分配し、トルエン層を食塩水100mlで洗浄した後、硫酸ナトリウムで乾燥して、褐色透明の2−(2−ブロモプロピオニル)チオフェン(0.180mol)/トルエン溶液を得た。
[Reference Example 1]
<Preparation of 2- (2-bromopropionyl) thiophene / toluene solution>
To a solution composed of 25.2 g (0.180 mol) of 2-propionylthiophene and 29 g of methanol, 28.7 g (0.180 mol) of bromine was added dropwise at 30 to 35 ° C. over 30 minutes. Next, the reaction solution was cooled and then concentrated under reduced pressure until the concentrate became 43 g. The concentrate was partitioned between 80 ml of toluene and 80 ml of brine, and the toluene layer was washed with 100 ml of brine and then dried over sodium sulfate to give brown transparent 2- (2-bromopropionyl) thiophene (0.180 mol) / toluene. A solution was obtained.
〔参考例2〕
<2−チオフェンカルボキシミドアミド塩酸塩の合成>
2−シアノチオフェン110.8g(1.015mol)、脱水エタノール49.4g(1.072mol)及び脱水ジクロロメタン55gからなる溶液に、冷却下5〜10℃にて、塩化水素ガス54.8g(1.22mol)を吹き込み5時間撹拌後、冷蔵庫に4℃/3日間放置して固体を析出させた。該反応懸濁液を減圧乾固して、赤桃色結晶性固体の2−チオフェンイミド酸エチル塩酸塩194.9g(1.017mol、収率100%)を得た。
該固体を粉砕し、氷冷下に振とうしながら、アンモニア32.0g(1.88mol)及び脱水エタノール177gからなる溶液を少量ずつ加えた後、4時間撹拌し、室温に戻して更に一晩撹拌した。この懸濁液を減圧濃縮し184gのアメ状濃縮物を得た。該濃縮物にヘキサン/ジクロロメタン溶液(2:1体積比)380mlを加え撹拌して結晶を析出させた。該結晶をろ取し、ヘキサン/ジクロロメタン溶液で洗浄後、減圧下に乾燥して、桃白色粉末状の2−チオフェンカルボキシミドアミド塩酸塩147.0g(0.904mol、収率89.1%)を得た。
[Reference Example 2]
<Synthesis of 2-thiophenecarboximidamide hydrochloride>
To a solution consisting of 110.8 g (1.015 mol) of 2-cyanothiophene, 49.4 g (1.072 mol) of dehydrated ethanol and 55 g of dehydrated dichloromethane, 54.8 g (1. 22 mol) was blown and stirred for 5 hours, and then left in a refrigerator at 4 ° C./3 days to precipitate a solid. The reaction suspension was dried under reduced pressure to obtain 194.9 g (1.017 mol, yield: 100%) of 2-thiophenimidic acid ethyl hydrochloride as a red pink crystalline solid.
The solid was pulverized, and a solution consisting of 32.0 g (1.88 mol) of ammonia and 177 g of dehydrated ethanol was added little by little while shaking under ice cooling, followed by stirring for 4 hours, returning to room temperature and further overnight. Stir. This suspension was concentrated under reduced pressure to obtain 184 g of a candy-like concentrate. To the concentrate, 380 ml of a hexane / dichloromethane solution (2: 1 volume ratio) was added and stirred to precipitate crystals. The crystals were collected by filtration, washed with a hexane / dichloromethane solution, and then dried under reduced pressure to give 147.0 g (0.904 mol, yield 89.1%) of 2-thiophenecarboximidamide hydrochloride in the form of a peach white powder. Got.
〔実施例1〕
<5−メチル−2−フェニル−4−(2−チエニル)イミダゾールの合成>
ベンズアミジン塩酸塩28.2g(0.180mol)をN,N−ジメチルアセトアミド60gに35℃にて加温溶解させ、炭酸カリウム82g(0.593mol)を加えて53〜57℃/40分間撹拌後、参考例1において調製した2−(2−ブロモプロピオニル)チオフェン/トルエン溶液を57〜69℃にて55分かけて滴下した。滴下終了後、68〜70℃/2時間30分間撹拌した。
次いで、反応懸濁液を冷却後、水500mlと撹拌し、分液した有機層を水500mlで洗浄し結晶を析出させた。結晶をろ取しトルエン、次いで熱水で分散洗浄し、ウエットの淡黄色粉末を得た。該粉末をアセトニトリルより再結晶して、黄白色粉末25.5gを得た。
[Example 1]
<Synthesis of 5-methyl-2-phenyl-4- (2-thienyl) imidazole>
Benzamidine hydrochloride 28.2 g (0.180 mol) was dissolved in N, N-dimethylacetamide 60 g by heating at 35 ° C., potassium carbonate 82 g (0.593 mol) was added, and the mixture was stirred at 53 to 57 ° C./40 minutes. The 2- (2-bromopropionyl) thiophene / toluene solution prepared in Reference Example 1 was added dropwise at 57 to 69 ° C. over 55 minutes. After completion of dropping, the mixture was stirred at 68 to 70 ° C./2 hours 30 minutes.
Next, the reaction suspension was cooled, stirred with 500 ml of water, and the separated organic layer was washed with 500 ml of water to precipitate crystals. The crystals were collected by filtration and dispersed and washed with toluene and then with hot water to obtain a wet pale yellow powder. The powder was recrystallized from acetonitrile to obtain 25.5 g of a yellowish white powder.
得られた粉末の融点、薄層クロマトグラフィーのRf値、1H NMR及びマススペクトルデータは、以下のとおりであった。
・mp202−206℃
・TLC(シリカゲル,アセトン):Rf=0.69
・1H NMR(DMSO-d6):δ=2.46(s,3H),7.09−7.95(m,8H).
・MS(EI):m/z(%)=240(M+,100),207(2),195(2),171(3),136(5),120(3),110(8),103(3),95(6),77(4).
これらのスペクトルデータから、得られた粉末は、化学式(IV)で示される5−メチル−2−フェニル−4−(2−チエニル)イミダゾールであるものと同定した。収率58.9%。
The melting point of the obtained powder, Rf value of thin layer chromatography, 1 H NMR and mass spectrum data were as follows.
・ Mp202-206 ℃
・ TLC (silica gel, acetone): Rf = 0.69
1 H NMR (DMSO-d 6 ): δ = 2.46 (s, 3H), 7.09-7.95 (m, 8H).
MS (EI): m / z (%) = 240 (M + , 100), 207 (2), 195 (2), 171 (3), 136 (5), 120 (3), 110 (8) 103 (3), 95 (6), 77 (4).
From these spectrum data, the obtained powder was identified as 5-methyl-2-phenyl-4- (2-thienyl) imidazole represented by the chemical formula (IV). Yield 58.9%.
〔実施例2〕
<5−メチル−2,4−ジ(2−チエニル)イミダゾールの合成>
実施例1のベンズアミジン塩酸塩を参考例2において調製した2−チオフェンカルボキシミドアミド塩酸塩に代えて、実施例1の方法に準拠して合成試験を行い、淡ベージュ色粉末を得た。
[Example 2]
<Synthesis of 5-methyl-2,4-di (2-thienyl) imidazole>
A synthetic test was conducted according to the method of Example 1 in place of the benzamidine hydrochloride of Example 1 instead of 2-thiophenecarboxamide amide hydrochloride prepared in Reference Example 2, and a light beige powder was obtained.
得られた粉末の融点、薄層クロマトグラフィーのRf値、1H NMR及びマススペクトルデータは、以下のとおりであった。
・mp199−203℃
・TLC(シリカゲル,アセトン):Rf=0.70
・1H NMR(DMSO-d6):δ=2.43(s,3H),7.08−7.51(m,6H).
・MS(EI):m/z(%)=246(M+,100),213(2),201(2),178(5),136(6),123(3),110(12),96(7).
これらのスペクトルデータから、得られた粉末は、化学式(V)で示される5−メチル−2,4−ジ(2−チエニル)イミダゾールであるものと同定した。収率36.0%。
The melting point of the obtained powder, Rf value of thin layer chromatography, 1 H NMR and mass spectrum data were as follows.
・ Mp199-203 ℃
・ TLC (silica gel, acetone): Rf = 0.70
1 H NMR (DMSO-d 6 ): δ = 2.43 (s, 3H), 7.08-7.51 (m, 6H).
MS (EI): m / z (%) = 246 (M + , 100), 213 (2), 201 (2), 178 (5), 136 (6), 123 (3), 110 (12) 96 (7).
From these spectral data, the obtained powder was identified to be 5-methyl-2,4-di (2-thienyl) imidazole represented by the chemical formula (V). Yield 36.0%.
〔実施例3〕
<2−(2,4−ジクロロベンジル)−4−(2−チエニル)イミダゾールの合成>
まず、参考例1の2−プロピオニルチオフェンを2−アセチルチオフェンに代えて、参考例1の方法に準拠して2−(2−ブロモアセチル)チオフェン/トルエン溶液を調製し、参考例2の2−シアノチオフェンを2,4−ジクロロベンジルシアニドに代えて、参考例2の方法に準拠して(2,4−ジクロロフェニル)アセトアミジン塩酸塩を調製した。
次いで、実施例1のベンズアミジン塩酸塩を(2,4−ジクロロフェニル)アセトアミジン塩酸塩に代えて、2−(2−ブロモプロピオニル)チオフェン/トルエン溶液を2−(2−ブロモアセチル)チオフェン/トルエン溶液に代えて、実施例1の方法に準拠して合成試験を行い、乳白色微結晶を得た。
Example 3
<Synthesis of 2- (2,4-dichlorobenzyl) -4- (2-thienyl) imidazole>
First, a 2- (2-bromoacetyl) thiophene / toluene solution was prepared according to the method of Reference Example 1 by replacing 2-propionylthiophene of Reference Example 1 with 2-acetylthiophene, and 2- (2,4-Dichlorophenyl) acetamidine hydrochloride was prepared according to the method of Reference Example 2 by replacing cyanothiophene with 2,4-dichlorobenzyl cyanide.
Subsequently, the benzamidine hydrochloride of Example 1 was replaced with (2,4-dichlorophenyl) acetamidine hydrochloride, and the 2- (2-bromopropionyl) thiophene / toluene solution was replaced with the 2- (2-bromoacetyl) thiophene / toluene solution. Instead of the above, a synthetic test was conducted in accordance with the method of Example 1 to obtain milky white fine crystals.
得られた結晶の融点、薄層クロマトグラフィーのRf値、1H NMR及びマススペクトルデータは、以下のとおりであった。
・mp147−149℃
・TLC(シリカゲル,アセトン):Rf=0.69
・1H NMR(DMSO-d6):δ=4.10(s,2H),7.00−7.61(m,7H).
・MS(EI):m/z(%)=310(M+2,40),308(M+,57),273(100),238(52),210(2),159(7),136(5),119(8),109(5),
96(13).
これらのスペクトルデータから、得られた結晶は、化学式(VI)で示される2−(2,4−ジクロロベンジル)−4−(2−チエニル)イミダゾールであるものと同定した。収率38.5%。
The melting point of the obtained crystal, Rf value of thin layer chromatography, 1 H NMR and mass spectral data were as follows.
・ Mp147-149 ℃
・ TLC (silica gel, acetone): Rf = 0.69
1 H NMR (DMSO-d 6 ): δ = 4.10 (s, 2H), 7.00-7.61 (m, 7H).
MS (EI): m / z (%) = 310 (M + 2, 40), 308 (M + , 57), 273 (100), 238 (52), 210 (2), 159 (7), 136 (5), 119 (8), 109 (5),
96 (13).
From these spectral data, the obtained crystal was identified as 2- (2,4-dichlorobenzyl) -4- (2-thienyl) imidazole represented by the chemical formula (VI). Yield 38.5%.
〔実施例4〕
まず、実施例1〜3において合成した4−(2−チエニル)イミダゾール化合物と、これらとは別に2−フェニルイミダゾール(2PZ、四国化成工業製)を有効成分とする銅の酸化防止剤を各々調製した。次いで、該防止剤に銅を接触させることにより銅の表面に化成皮膜を形成させた。そして、銅に対する溶融半田の濡れ時間を測定して、イミダゾール化合物が作用する銅表面への酸化防止性能を評価した。この場合、溶融半田の濡れ時間が短い程、イミダゾール化合物の酸化防止性能が優れているものと判定される。
評価試験の詳細は、次のとおりである。
(1)酸化防止剤の調製
イミダゾール化合物、酸、金属塩及びハロゲン化合物を、表1記載の組成となるようにイオン交換水に溶解させた後、アンモニア水でpHを調整して酸化防止剤を調製した。
(2)表面処理方法
材質が金属銅の試験片(5mm×50mm×0.3mmの銅版)を脱脂し、次いでソフトエッチングを行い、所定温度の酸化防止剤に所定時間浸漬して、銅の表面に化成皮膜を形成させた後、水洗して乾燥した。
(3)濡れ時間の測定
表面処理を行った試験片を、ポストフラックス(JS−64MSS、弘輝製)に浸漬して、半田濡れ性試験器(SAT−2000、レスカ製)を使用して半田濡れ時間(秒)を測定した。使用した半田は錫−鉛系共晶半田(H63A−B20、千住金属工業製)であり、測定条件は半田温度240℃、浸漬深さ2mm、浸漬スピード16mm/秒とした。
なお、半田濡れ時間を測定した試験片は、(A)表面処理直後のものと、(B)温度40℃、湿度90%RHの恒温恒湿器に入れて96時間放置したものと、(C)さらに200℃で10分間加熱したものである。
得られた試験結果は、表1に示したとおりであった。
Example 4
First, a 4- (2-thienyl) imidazole compound synthesized in Examples 1 to 3 and a copper antioxidant containing 2-phenylimidazole (2PZ, manufactured by Shikoku Kasei Kogyo Co., Ltd.) as an active ingredient are prepared separately. did. Next, a chemical conversion film was formed on the surface of copper by bringing the inhibitor into contact with copper. And the wetting time of the molten solder with respect to copper was measured, and the antioxidant performance to the copper surface on which an imidazole compound acts was evaluated. In this case, it is determined that the shorter the wet time of the molten solder, the better the antioxidant performance of the imidazole compound.
The details of the evaluation test are as follows.
(1) Preparation of antioxidant After dissolving an imidazole compound, an acid, a metal salt, and a halogen compound in ion-exchanged water so as to have the composition shown in Table 1, the pH is adjusted with ammonia water to thereby add an antioxidant. Prepared.
(2) Surface treatment method A test piece (copper plate of 5 mm × 50 mm × 0.3 mm) made of metallic copper is degreased, then soft-etched, and immersed in an antioxidant at a predetermined temperature for a predetermined time to obtain a copper surface. After the chemical conversion film was formed on, it was washed with water and dried.
(3) Measurement of wetting time The surface-treated test piece is immersed in post-flux (JS-64MSS, manufactured by Hiroki) and solder wetted using a solder wettability tester (SAT-2000, manufactured by Resuka). Time (seconds) was measured. The solder used was tin-lead eutectic solder (H63A-B20, manufactured by Senju Metal Industry), and the measurement conditions were a solder temperature of 240 ° C., an immersion depth of 2 mm, and an immersion speed of 16 mm / second.
In addition, the test piece which measured the solder wetting time includes (A) a sample immediately after the surface treatment, (B) a sample left in a constant temperature and humidity chamber at a temperature of 40 ° C. and a humidity of 90% RH for 96 hours, and (C ) Further heated at 200 ° C. for 10 minutes.
The test results obtained were as shown in Table 1.
表1に示した試験結果によれば、本願発明の4−(2−チエニル)イミダゾール化合物を有効成分として含有する酸化防止剤は、銅の表面に耐湿性及び耐熱性に優れた化成皮膜を形成させることができるので、銅表面の酸化防止に有用である。 According to the test results shown in Table 1, the antioxidant containing the 4- (2-thienyl) imidazole compound of the present invention as an active ingredient forms a chemical conversion film excellent in moisture resistance and heat resistance on the surface of copper. Therefore, it is useful for preventing oxidation of the copper surface.
本発明によれば、金属、特に銅(銅合金を含む)の表面の酸化防止剤や、エポキシ樹脂の硬化剤又は硬化促進剤として、また医農薬分野の中間原料としても有用な4−(2−チエニル)イミダゾール化合物を提供することができる。 According to the present invention, 4- (2) useful as an antioxidant for the surface of metals, particularly copper (including copper alloys), as a curing agent or accelerator for epoxy resins, and as an intermediate material in the field of medicine and agrochemicals. -Thienyl) imidazole compounds can be provided.
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