CA1154025A - Composes basiques derives du styrene, et methode pour les preparer - Google Patents

Composes basiques derives du styrene, et methode pour les preparer

Info

Publication number: CA1154025A
Authority: CA; Canada
Prior art keywords: group; reaction; process according; mixture; compounds
Prior art date: 1979-07-19
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.): Expired

Application number

CA000356454A

Other languages

English (en)

Inventor

Tetsuya Miyake

Kunihiko Takeda

Keishi Tada

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Asahi Kasei Corp

Original Assignee

Asahi Kasei Kogyo KK

Priority date (The priority date 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 date listed.)

1979-07-19

Filing date

1980-07-18

Publication date

1983-09-20

1980-07-18 Application filed by Asahi Kasei Kogyo KK filed Critical Asahi Kasei Kogyo KK

1983-09-20 Application granted granted Critical

1983-09-20 Publication of CA1154025A publication Critical patent/CA1154025A/fr

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims description 26
238000002360 preparation method Methods 0.000 title claims description 5
125000003011 styrenyl group Chemical class [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 title 1
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims abstract description 40
150000007514 bases Chemical class 0.000 claims abstract description 18
-1 imidazole compound Chemical class 0.000 claims abstract description 15
238000006243 chemical reaction Methods 0.000 claims description 52
239000000203 mixture Substances 0.000 claims description 37
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 25
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 23
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 16
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 15
150000001875 compounds Chemical class 0.000 claims description 13
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
239000012442 inert solvent Substances 0.000 claims description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 9
238000006116 polymerization reaction Methods 0.000 claims description 9
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 8
239000003112 inhibitor Substances 0.000 claims description 8
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
125000000217 alkyl group Chemical group 0.000 claims description 7
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
229910052751 metal Inorganic materials 0.000 claims description 6
239000002184 metal Substances 0.000 claims description 6
229910001507 metal halide Inorganic materials 0.000 claims description 6
150000005309 metal halides Chemical class 0.000 claims description 6
150000002739 metals Chemical class 0.000 claims description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
HMDQPBSDHHTRNI-UHFFFAOYSA-N 1-(chloromethyl)-3-ethenylbenzene Chemical group ClCC1=CC=CC(C=C)=C1 HMDQPBSDHHTRNI-UHFFFAOYSA-N 0.000 claims description 4
ZRZHXNCATOYMJH-UHFFFAOYSA-N 1-(chloromethyl)-4-ethenylbenzene Chemical compound ClCC1=CC=C(C=C)C=C1 ZRZHXNCATOYMJH-UHFFFAOYSA-N 0.000 claims description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 4
125000003277 amino group Chemical group 0.000 claims description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 4
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 4
235000017557 sodium bicarbonate Nutrition 0.000 claims description 4
125000001424 substituent group Chemical group 0.000 claims description 4
229910021591 Copper(I) chloride Inorganic materials 0.000 claims description 3
125000004432 carbon atom Chemical group C* 0.000 claims description 3
OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 claims description 3
229940045803 cuprous chloride Drugs 0.000 claims description 3
229960002089 ferrous chloride Drugs 0.000 claims description 3
125000002883 imidazolyl group Chemical group 0.000 claims description 3
229910052742 iron Inorganic materials 0.000 claims description 3
NMCUIPGRVMDVDB-UHFFFAOYSA-L iron dichloride Chemical compound Cl[Fe]Cl NMCUIPGRVMDVDB-UHFFFAOYSA-L 0.000 claims description 3
TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 claims description 2
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 2
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 2
229910021626 Tin(II) chloride Inorganic materials 0.000 claims description 2
229940063656 aluminum chloride Drugs 0.000 claims description 2
229910052802 copper Inorganic materials 0.000 claims description 2
239000010949 copper Substances 0.000 claims description 2
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
239000001119 stannous chloride Substances 0.000 claims description 2
235000011150 stannous chloride Nutrition 0.000 claims description 2
229940013123 stannous chloride Drugs 0.000 claims description 2
229910052718 tin Inorganic materials 0.000 claims description 2
239000011135 tin Substances 0.000 claims description 2
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 1
229940027987 antiseptic and disinfectant phenol and derivative Drugs 0.000 claims 1
229910052794 bromium Inorganic materials 0.000 claims 1
229910052801 chlorine Inorganic materials 0.000 claims 1
125000000687 hydroquinonyl group Chemical class C1(O)=C(C=C(O)C=C1)* 0.000 claims 1
229910052740 iodine Inorganic materials 0.000 claims 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 1
239000011734 sodium Substances 0.000 claims 1
229910052708 sodium Inorganic materials 0.000 claims 1
239000003822 epoxy resin Substances 0.000 abstract description 4
229920000647 polyepoxide Polymers 0.000 abstract description 4
239000003795 chemical substances by application Substances 0.000 abstract 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 abstract description 2
HIRSRDFJHKZRKJ-UHFFFAOYSA-N 2-[(1-ethenylcyclohexa-2,4-dien-1-yl)methyl]-1h-imidazole Chemical class N=1C=CNC=1CC1(C=C)CC=CC=C1 HIRSRDFJHKZRKJ-UHFFFAOYSA-N 0.000 abstract 1
239000000243 solution Substances 0.000 description 30
239000000047 product Substances 0.000 description 28
238000004458 analytical method Methods 0.000 description 26
239000000126 substance Substances 0.000 description 19
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 16
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
IWTYTFSSTWXZFU-UHFFFAOYSA-N 3-chloroprop-1-enylbenzene Chemical class ClCC=CC1=CC=CC=C1 IWTYTFSSTWXZFU-UHFFFAOYSA-N 0.000 description 13
239000007788 liquid Substances 0.000 description 13
239000011541 reaction mixture Substances 0.000 description 13
238000010992 reflux Methods 0.000 description 12
238000004811 liquid chromatography Methods 0.000 description 10
238000000862 absorption spectrum Methods 0.000 description 9
238000003756 stirring Methods 0.000 description 9
VYDWQPKRHOGLPA-UHFFFAOYSA-N 5-nitroimidazole Chemical compound [O-][N+](=O)C1=CN=CN1 VYDWQPKRHOGLPA-UHFFFAOYSA-N 0.000 description 7
238000013019 agitation Methods 0.000 description 7
238000001819 mass spectrum Methods 0.000 description 7
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 7
LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 6
101150041968 CDC13 gene Proteins 0.000 description 6
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
239000007795 chemical reaction product Substances 0.000 description 6
238000004821 distillation Methods 0.000 description 6
238000000605 extraction Methods 0.000 description 6
XESZUVZBAMCAEJ-UHFFFAOYSA-N 4-tert-butylcatechol Chemical compound CC(C)(C)C1=CC=C(O)C(O)=C1 XESZUVZBAMCAEJ-UHFFFAOYSA-N 0.000 description 5
239000007864 aqueous solution Substances 0.000 description 5
238000009614 chemical analysis method Methods 0.000 description 5
BGNXCDMCOKJUMV-UHFFFAOYSA-N Tert-Butylhydroquinone Chemical compound CC(C)(C)C1=CC(O)=CC=C1O BGNXCDMCOKJUMV-UHFFFAOYSA-N 0.000 description 4
239000004250 tert-Butylhydroquinone Substances 0.000 description 4
235000019281 tert-butylhydroquinone Nutrition 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
WRYNUJYAXVDTCB-UHFFFAOYSA-M acetyloxymercury Chemical compound CC(=O)O[Hg] WRYNUJYAXVDTCB-UHFFFAOYSA-M 0.000 description 3
238000001914 filtration Methods 0.000 description 3
YTWBFUCJVWKCCK-UHFFFAOYSA-N 2-heptadecyl-1h-imidazole Chemical compound CCCCCCCCCCCCCCCCCC1=NC=CN1 YTWBFUCJVWKCCK-UHFFFAOYSA-N 0.000 description 2
ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 2-phenyl-1h-imidazole Chemical compound C1=CNC(C=2C=CC=CC=2)=N1 ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 0.000 description 2
HXIQYSLFEXIOAV-UHFFFAOYSA-N 2-tert-butyl-4-(5-tert-butyl-4-hydroxy-2-methylphenyl)sulfanyl-5-methylphenol Chemical compound CC1=CC(O)=C(C(C)(C)C)C=C1SC1=CC(C(C)(C)C)=C(O)C=C1C HXIQYSLFEXIOAV-UHFFFAOYSA-N 0.000 description 2
LLEASVZEQBICSN-UHFFFAOYSA-N 2-undecyl-1h-imidazole Chemical compound CCCCCCCCCCCC1=NC=CN1 LLEASVZEQBICSN-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-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
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
150000002460 imidazoles Chemical class 0.000 description 2
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
DAHPIMYBWVSMKQ-UHFFFAOYSA-N n-hydroxy-n-phenylnitrous amide Chemical compound O=NN(O)C1=CC=CC=C1 DAHPIMYBWVSMKQ-UHFFFAOYSA-N 0.000 description 2
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
239000007787 solid Substances 0.000 description 2
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical class CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 1
VTPQLJUADNBKRM-UHFFFAOYSA-N 1-(bromomethyl)-4-ethenylbenzene Chemical compound BrCC1=CC=C(C=C)C=C1 VTPQLJUADNBKRM-UHFFFAOYSA-N 0.000 description 1
WYLLBCFMGHLSPC-UHFFFAOYSA-N 1-[(3-ethenylphenyl)methyl]-4-nitroimidazole Chemical compound C1=NC([N+](=O)[O-])=CN1CC1=CC=CC(C=C)=C1 WYLLBCFMGHLSPC-UHFFFAOYSA-N 0.000 description 1
FJNMHXUJLRRWAQ-UHFFFAOYSA-N 1-[(4-ethenylphenyl)methyl]-2-methylimidazole Chemical compound CC1=NC=CN1CC1=CC=C(C=C)C=C1 FJNMHXUJLRRWAQ-UHFFFAOYSA-N 0.000 description 1
ZNBGLRLMJCONPA-UHFFFAOYSA-N 1-[(4-ethenylphenyl)methyl]-2-undecylimidazole Chemical compound CCCCCCCCCCCC1=NC=CN1CC1=CC=C(C=C)C=C1 ZNBGLRLMJCONPA-UHFFFAOYSA-N 0.000 description 1
DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical class CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
JZODKRWQWUWGCD-UHFFFAOYSA-N 2,5-di-tert-butylbenzene-1,4-diol Chemical compound CC(C)(C)C1=CC(O)=C(C(C)(C)C)C=C1O JZODKRWQWUWGCD-UHFFFAOYSA-N 0.000 description 1
KUBDPQJOLOUJRM-UHFFFAOYSA-N 2-(chloromethyl)oxirane;4-[2-(4-hydroxyphenyl)propan-2-yl]phenol Chemical compound ClCC1CO1.C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 KUBDPQJOLOUJRM-UHFFFAOYSA-N 0.000 description 1
FFYTTYVSDVWNMY-UHFFFAOYSA-N 2-Methyl-5-nitroimidazole Chemical compound CC1=NC=C([N+]([O-])=O)N1 FFYTTYVSDVWNMY-UHFFFAOYSA-N 0.000 description 1
LLQHNYLFWACOCL-UHFFFAOYSA-N 2-[(3-ethenylphenyl)methyl]-1h-imidazole Chemical compound C=CC1=CC=CC(CC=2NC=CN=2)=C1 LLQHNYLFWACOCL-UHFFFAOYSA-N 0.000 description 1
UURMIDPHCPPZBL-UHFFFAOYSA-N 2-[(4-ethenylphenyl)methyl]-1h-imidazole Chemical compound C1=CC(C=C)=CC=C1CC1=NC=CN1 UURMIDPHCPPZBL-UHFFFAOYSA-N 0.000 description 1
ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
YZEUHQHUFTYLPH-UHFFFAOYSA-N 2-nitroimidazole Chemical compound [O-][N+](=O)C1=NC=CN1 YZEUHQHUFTYLPH-UHFFFAOYSA-N 0.000 description 1
PFANXOISJYKQRP-UHFFFAOYSA-N 2-tert-butyl-4-[1-(5-tert-butyl-4-hydroxy-2-methylphenyl)butyl]-5-methylphenol Chemical compound C=1C(C(C)(C)C)=C(O)C=C(C)C=1C(CCC)C1=CC(C(C)(C)C)=C(O)C=C1C PFANXOISJYKQRP-UHFFFAOYSA-N 0.000 description 1
IMOYOUMVYICGCA-UHFFFAOYSA-N 2-tert-butyl-4-hydroxyanisole Chemical compound COC1=CC=C(O)C=C1C(C)(C)C IMOYOUMVYICGCA-UHFFFAOYSA-N 0.000 description 1
RUROFEVDCUGKHD-UHFFFAOYSA-N 3-bromoprop-1-enylbenzene Chemical class BrCC=CC1=CC=CC=C1 RUROFEVDCUGKHD-UHFFFAOYSA-N 0.000 description 1
XLSZMDLNRCVEIJ-UHFFFAOYSA-N 4-methylimidazole Chemical class CC1=CNC=N1 XLSZMDLNRCVEIJ-UHFFFAOYSA-N 0.000 description 1
SQZCZXRYOJJCDU-UHFFFAOYSA-N 5-nitro-2-propan-2-yl-1h-imidazole Chemical compound CC(C)C1=NC=C([N+]([O-])=O)N1 SQZCZXRYOJJCDU-UHFFFAOYSA-N 0.000 description 1
JQJPBYFTQAANLE-UHFFFAOYSA-N Butyl nitrite Chemical compound CCCCON=O JQJPBYFTQAANLE-UHFFFAOYSA-N 0.000 description 1
NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
239000004593 Epoxy Substances 0.000 description 1
XOBKSJJDNFUZPF-UHFFFAOYSA-N Methoxyethane Chemical compound CCOC XOBKSJJDNFUZPF-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
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
QMDOZWIDXVOGOH-UHFFFAOYSA-N [N+](=O)([O-])C=1N=CNC1.[N+](=O)([O-])C1=CN=CN1 Chemical compound [N+](=O)([O-])C=1N=CNC1.[N+](=O)([O-])C1=CN=CN1 QMDOZWIDXVOGOH-UHFFFAOYSA-N 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
235000010354 butylated hydroxytoluene Nutrition 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000012790 confirmation Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
229940113088 dimethylacetamide Drugs 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
230000008014 freezing Effects 0.000 description 1
238000007710 freezing Methods 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
125000001145 hydrido group Chemical group *[H] 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
125000000018 nitroso group Chemical group N(=O)* 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000000376 reactant Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical class CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
150000003440 styrenes Chemical class 0.000 description 1
150000003462 sulfoxides Chemical class 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1
150000003738 xylenes Chemical class 0.000 description 1
LRXTYHSAJDENHV-UHFFFAOYSA-H zinc phosphate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O LRXTYHSAJDENHV-UHFFFAOYSA-H 0.000 description 1
229910000165 zinc phosphate Inorganic materials 0.000 description 1

Classifications

- 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
- C07D233/56—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 only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- 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
- 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
- C07D233/66—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/91—Nitro radicals
- C07D233/92—Nitro radicals attached in position 4 or 5
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

CA000356454A 1979-07-19 1980-07-18 Composes basiques derives du styrene, et methode pour les preparer Expired CA1154025A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
JP54-90901		1979-07-19
JP9090179A JPS6047257B2 (ja)	1979-07-19	1979-07-19	新規な塩基性物質およびその製造法

Publications (1)

Publication Number	Publication Date
CA1154025A true CA1154025A (fr)	1983-09-20

Family

ID=14011293

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000356454A Expired CA1154025A (fr)	1979-07-19	1980-07-18	Composes basiques derives du styrene, et methode pour les preparer

Country Status (8)

Country	Link
JP (1)	JPS6047257B2 (fr)
AU (1)	AU530504B2 (fr)
BE (1)	BE884355A (fr)
CA (1)	CA1154025A (fr)
DE (1)	DE3026410C2 (fr)
FR (1)	FR2461704A1 (fr)
GB (1)	GB2054567B (fr)
NL (1)	NL8004166A (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB2125416B (en) *	1982-07-14	1985-11-27	Asahi Chemical Ind	Imidazolylmethyl styrene polymers use thereof as ion exchange resins
DE3811574A1 (de) *	1988-03-31	1989-10-19	Schering Ag	N-substituierte imidazole, verfahren zu ihrer herstellung sowie ihre verwendung in arzneimitteln
WO2004041809A2 (fr)	2002-05-08	2004-05-21	Neurogen Corporation	Imidazolylmethyl pyridine substituee et derives de pyrazine: les ligands des recepteurs gabaa

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US443563A (en) *		1890-12-30		Sigmund bergmann
US3226372A (en) *	1961-06-02	1965-12-28	Dow Chemical Co	Novel heterocyclic compounds and polymers
MC1221A1 (fr) *	1977-10-19	1979-07-20	Wellcome Found	Derives de l'imidazole et leurs sels,leur synthese et leurs produits intermediaires,et preparation de compositions pharmaceutiques contenant ces substances

1979
- 1979-07-19 JP JP9090179A patent/JPS6047257B2/ja not_active Expired
1980
- 1980-06-26 GB GB8020971A patent/GB2054567B/en not_active Expired
- 1980-07-09 AU AU60258/80A patent/AU530504B2/en not_active Ceased
- 1980-07-11 FR FR8015523A patent/FR2461704A1/fr active Granted
- 1980-07-11 DE DE19803026410 patent/DE3026410C2/de not_active Expired
- 1980-07-17 BE BE0/201437A patent/BE884355A/fr not_active IP Right Cessation
- 1980-07-18 CA CA000356454A patent/CA1154025A/fr not_active Expired
- 1980-07-18 NL NL8004166A patent/NL8004166A/nl active Search and Examination

Also Published As

Publication number	Publication date
GB2054567A (en)	1981-02-18
DE3026410C2 (de)	1987-01-02
AU6025880A (en)	1981-01-22
BE884355A (fr)	1981-01-19
NL8004166A (nl)	1981-01-21
JPS6047257B2 (ja)	1985-10-21
GB2054567B (en)	1983-09-21
DE3026410A1 (de)	1981-02-05
FR2461704A1 (fr)	1981-02-06
AU530504B2 (en)	1983-07-21
FR2461704B1 (fr)	1985-01-04
JPS5616471A (en)	1981-02-17

Legal Events

Date	Code	Title	Description
2000-09-20	MKEX	Expiry

Publication	Publication Date	Title
US5438151A (en)	1995-08-01	Process for the preparation of ergothioneine
US4182862A (en)	1980-01-08	Process for the preparation of 1,3-disubstituted-2-azoyl-2-propen-1-ones
Kamijo et al.	1983	An improved and convenient procedure for the synthesis of 1-substituted imidazoles
CA1304741C (fr)	1992-07-07	Compose heterocyclique
CA1154025A (fr)	1983-09-20	Composes basiques derives du styrene, et methode pour les preparer
WO1984003885A1 (fr)	1984-10-11	Composes d'hydrure de bore modifies de maniere asymetrique, leur procede de preparation et procede de preparation de derives d'alcool optiquement actifs utilisant ces composes
US4632999A (en)	1986-12-30	Process for the preparation of oxiranes
US5179210A (en)	1993-01-12	Preparation of n-substituted imidazoles
EP0005219B1 (fr)	1981-07-22	Arylimidazoles, procédé pour leur préparation et compositions pharmaceutiques et vétérinaires les renfermant
JP3887836B2 (ja)	2007-02-28	Ｎ−メチルイミダゾール類の製造法
Simenel et al.	2003	Simple route to ferrocenyl (alkyl) imidazoles
JPS6118790A (ja)	1986-01-27	光学活性ボラン錯体およびその製造法
GB1472290A (en)	1977-05-04	Preparation of n-alkyl diphenyl pyrazoles
Jones et al.	1987	A radiochemical study of the kinetics of epoxide cure: Reaction of phenyl glycidyl ether and other model epoxides with various imidazoles
PL138476B1 (en)	1986-09-30	Method of obtaining novel derivatives of triazole
US5008398A (en)	1991-04-16	Preparation of p-nitrophenyl-imidazoles
JPH06135869A (ja)	1994-05-17	ペルフルオロアルキル基を持つ化合物の製造法
EP0218398A2 (fr)	1987-04-15	Dérivés d'imidazole utiles comme agents fongicides et leurs procédés de préparation
FI71311B (fi)	1986-09-09	Foerfarande foer stereospecifik framstaellning av imidazolyl-oximderivat och imidazolyl-oximeterderivat
CA1119179A (fr)	1982-03-02	Procede d'obtention de composes a base de n-tritylimidazole
CA1120042A (fr)	1982-03-16	Methode de preparation de derives du n-tritylimidazole
Takeuchi et al.	1979	Acid-catalyzed isotope exchange of ring hydrogens in fluoroimidazoles
EP0060222B1 (fr)	1989-12-06	Halogène-méthyltriazoles
EP0046532B1 (fr)	1983-09-14	3,3-Diméthyl-1-fluoro-1-phénoxy-2-butanones(ols), procédé pour leur préparation et leur utilisation
DE69031315T2 (de)	1998-01-22	Verfahren zur Herstellung von optisch aktivem Alkohol