JPS5910348B2 - ハロゲン置換ベンゾイミダゾロン誘導体の製造方法 - Google Patents
ハロゲン置換ベンゾイミダゾロン誘導体の製造方法Info
- Publication number
- JPS5910348B2 JPS5910348B2 JP49130917A JP13091774A JPS5910348B2 JP S5910348 B2 JPS5910348 B2 JP S5910348B2 JP 49130917 A JP49130917 A JP 49130917A JP 13091774 A JP13091774 A JP 13091774A JP S5910348 B2 JPS5910348 B2 JP S5910348B2
- Authority
- JP
- Japan
- Prior art keywords
- benzimidazolone
- mol
- melting point
- product
- reaction
- 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.)
- Expired
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 39
- 150000008641 benzimidazolones Chemical class 0.000 title claims description 14
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 30
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 27
- 229910052794 bromium Inorganic materials 0.000 claims description 27
- 229910052801 chlorine Inorganic materials 0.000 claims description 13
- 239000000460 chlorine Substances 0.000 claims description 10
- 239000000126 substance Substances 0.000 claims description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 238000002844 melting Methods 0.000 description 49
- 230000008018 melting Effects 0.000 description 49
- 239000000047 product Substances 0.000 description 46
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 42
- 238000006243 chemical reaction Methods 0.000 description 39
- 239000013078 crystal Substances 0.000 description 37
- 239000000243 solution Substances 0.000 description 29
- 150000001875 compounds Chemical class 0.000 description 26
- 238000000921 elemental analysis Methods 0.000 description 25
- 238000003756 stirring Methods 0.000 description 25
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 23
- 239000002244 precipitate Substances 0.000 description 22
- 239000012043 crude product Substances 0.000 description 21
- 238000000034 method Methods 0.000 description 20
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 19
- -1 bromine-substituted benzimidazolone Chemical class 0.000 description 18
- 239000012046 mixed solvent Substances 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 239000000203 mixture Substances 0.000 description 15
- 238000001228 spectrum Methods 0.000 description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- MYONAGGJKCJOBT-UHFFFAOYSA-N benzimidazol-2-one Chemical compound C1=CC=CC2=NC(=O)N=C21 MYONAGGJKCJOBT-UHFFFAOYSA-N 0.000 description 11
- 239000007858 starting material Substances 0.000 description 10
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 8
- 229920000728 polyester Polymers 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- 238000005893 bromination reaction Methods 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 230000031709 bromination Effects 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 239000005457 ice water Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-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
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 238000000967 suction filtration Methods 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-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
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 238000005273 aeration Methods 0.000 description 3
- 238000005660 chlorination reaction Methods 0.000 description 3
- 238000010908 decantation Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 239000011630 iodine Substances 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- MVGAEVPAVZNUFG-UHFFFAOYSA-N 1,3-bis(3-aminopropyl)benzimidazol-2-one Chemical class C1=CC=C2N(CCCN)C(=O)N(CCCN)C2=C1 MVGAEVPAVZNUFG-UHFFFAOYSA-N 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- CAAMSDWKXXPUJR-UHFFFAOYSA-N 3,5-dihydro-4H-imidazol-4-one Chemical compound O=C1CNC=N1 CAAMSDWKXXPUJR-UHFFFAOYSA-N 0.000 description 2
- TWNNMRWUJWLCKS-UHFFFAOYSA-N 3-[3-(2-cyanoethyl)-2-oxobenzimidazol-1-yl]propanenitrile Chemical compound C1=CC=C2N(CCC#N)C(=O)N(CCC#N)C2=C1 TWNNMRWUJWLCKS-UHFFFAOYSA-N 0.000 description 2
- JUZLMTKXVARGJJ-UHFFFAOYSA-N 4,5,6,7-tetrachlorobenzimidazol-2-one Chemical compound ClC1=C(Cl)C(Cl)=C(Cl)C2=NC(=O)N=C21 JUZLMTKXVARGJJ-UHFFFAOYSA-N 0.000 description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 230000005587 bubbling Effects 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 2
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000006068 polycondensation reaction Methods 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
- 239000006228 supernatant Substances 0.000 description 2
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 1
- VDUQJADUZSMRNM-UHFFFAOYSA-N 1,3-bis(2-hydroxy-2-phenylethyl)benzimidazol-2-one Chemical compound C=1C=CC=CC=1C(O)CN(C1=O)C2=CC=CC=C2N1CC(O)C1=CC=CC=C1 VDUQJADUZSMRNM-UHFFFAOYSA-N 0.000 description 1
- UARFFANGBYNLQT-UHFFFAOYSA-N 1,3-bis(2-hydroxyethyl)benzimidazol-2-one Chemical compound C1=CC=C2N(CCO)C(=O)N(CCO)C2=C1 UARFFANGBYNLQT-UHFFFAOYSA-N 0.000 description 1
- WAUNJESDGAPXMO-UHFFFAOYSA-N 1,3-bis(2-hydroxypropyl)benzimidazol-2-one Chemical compound C1=CC=C2N(CC(C)O)C(=O)N(CC(O)C)C2=C1 WAUNJESDGAPXMO-UHFFFAOYSA-N 0.000 description 1
- CNGROZGOFRTGFU-UHFFFAOYSA-N 1,3-bis(hydroxymethyl)benzimidazol-2-one Chemical compound C1=CC=C2N(CO)C(=O)N(CO)C2=C1 CNGROZGOFRTGFU-UHFFFAOYSA-N 0.000 description 1
- KPZGRMZPZLOPBS-UHFFFAOYSA-N 1,3-dichloro-2,2-bis(chloromethyl)propane Chemical compound ClCC(CCl)(CCl)CCl KPZGRMZPZLOPBS-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- JMTPLUIWGNLLNB-UHFFFAOYSA-N 2-[3-(carboxymethyl)-2-oxobenzimidazol-1-yl]acetic acid Chemical compound C1=CC=C2N(CC(O)=O)C(=O)N(CC(=O)O)C2=C1 JMTPLUIWGNLLNB-UHFFFAOYSA-N 0.000 description 1
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 1
- YKDAJIRBTYBBGD-UHFFFAOYSA-N 3-(2-oxobenzimidazol-4-yl)propanoic acid Chemical class OC(=O)CCC1=CC=CC2=NC(=O)N=C12 YKDAJIRBTYBBGD-UHFFFAOYSA-N 0.000 description 1
- RDKKEOHSGJVGCN-UHFFFAOYSA-N 3-[3-(2-carboxyethyl)-2-oxobenzimidazol-1-yl]propanoic acid Chemical compound C1=CC=C2N(CCC(O)=O)C(=O)N(CCC(=O)O)C2=C1 RDKKEOHSGJVGCN-UHFFFAOYSA-N 0.000 description 1
- DHXNZYCXMFBMHE-UHFFFAOYSA-N 3-bromopropanoic acid Chemical compound OC(=O)CCBr DHXNZYCXMFBMHE-UHFFFAOYSA-N 0.000 description 1
- KGXOHDDITRDHFO-UHFFFAOYSA-N 4,5,6,7-tetrachloro-1,3-bis(2-chloroethyl)benzimidazol-2-one Chemical compound ClC1=C(Cl)C(Cl)=C2N(CCCl)C(=O)N(CCCl)C2=C1Cl KGXOHDDITRDHFO-UHFFFAOYSA-N 0.000 description 1
- RLOFMIQCRDRKMM-UHFFFAOYSA-N 4,5,6,7-tetrachloro-1,3-bis(2-hydroxypropyl)benzimidazol-2-one Chemical compound ClC1=C(Cl)C(Cl)=C2N(CC(C)O)C(=O)N(CC(O)C)C2=C1Cl RLOFMIQCRDRKMM-UHFFFAOYSA-N 0.000 description 1
- YWPYTPJZYVZUBV-UHFFFAOYSA-N 4,5,6,7-tetrachloro-1,3-bis(ethenyl)benzimidazol-2-one Chemical compound ClC1=C(Cl)C(Cl)=C2N(C=C)C(=O)N(C=C)C2=C1Cl YWPYTPJZYVZUBV-UHFFFAOYSA-N 0.000 description 1
- YPTVDXWZPFNNEH-UHFFFAOYSA-N 4,5-dibromobenzimidazol-2-one Chemical compound BrC1=C(C=2C(=NC(N2)=O)C=C1)Br YPTVDXWZPFNNEH-UHFFFAOYSA-N 0.000 description 1
- VIKVFVYZVSIBSS-UHFFFAOYSA-N 5,6-dibromo-4,7-dichloro-1,3-bis(2-hydroxyethyl)benzimidazol-2-one Chemical compound BrC1=C(Br)C(Cl)=C2N(CCO)C(=O)N(CCO)C2=C1Cl VIKVFVYZVSIBSS-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- 108010077544 Chromatin Proteins 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 241000238557 Decapoda Species 0.000 description 1
- 241000192043 Echinochloa Species 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- OKIZCWYLBDKLSU-UHFFFAOYSA-M N,N,N-Trimethylmethanaminium chloride Chemical compound [Cl-].C[N+](C)(C)C OKIZCWYLBDKLSU-UHFFFAOYSA-M 0.000 description 1
- OEQNECSNVCVSFF-UHFFFAOYSA-N N=1C(N=C2C1C=CC=C2)=O.N=2C(N=C1C2C=CC=C1)=O Chemical compound N=1C(N=C2C1C=CC=C2)=O.N=2C(N=C1C2C=CC=C1)=O OEQNECSNVCVSFF-UHFFFAOYSA-N 0.000 description 1
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 1
- 229910021538 borax Inorganic materials 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 229940106681 chloroacetic acid Drugs 0.000 description 1
- XENVCRGQTABGKY-ZHACJKMWSA-N chlorohydrin Chemical compound CC#CC#CC#CC#C\C=C\C(Cl)CO XENVCRGQTABGKY-ZHACJKMWSA-N 0.000 description 1
- 210000003483 chromatin Anatomy 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- ZWAJLVLEBYIOTI-UHFFFAOYSA-N cyclohexene oxide Chemical compound C1CCCC2OC21 ZWAJLVLEBYIOTI-UHFFFAOYSA-N 0.000 description 1
- FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohexene oxide Natural products O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 description 1
- 238000007033 dehydrochlorination reaction Methods 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 235000011187 glycerol Nutrition 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
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- LOCAIGRSOJUCTB-UHFFFAOYSA-N indazol-3-one Chemical compound C1=CC=C2C(=O)N=NC2=C1 LOCAIGRSOJUCTB-UHFFFAOYSA-N 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000004702 methyl esters Chemical group 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920001707 polybutylene terephthalate Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 238000005201 scrubbing Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000004328 sodium tetraborate Substances 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles 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 in position 2
- C07D235/26—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
- C08G18/3819—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen
- C08G18/3842—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen containing heterocyclic rings having at least one nitrogen atom in the ring
- C08G18/3848—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen containing heterocyclic rings having at least one nitrogen atom in the ring containing two nitrogen atoms in the ring
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/22—Di-epoxy compounds
- C08G59/26—Di-epoxy compounds heterocyclic
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
- C08G63/685—Polyesters containing atoms other than carbon, hydrogen and oxygen containing nitrogen
- C08G63/6854—Polyesters containing atoms other than carbon, hydrogen and oxygen containing nitrogen derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/6856—Dicarboxylic acids and dihydroxy compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Polyesters Or Polycarbonates (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1595373A CH583201A5 (en, 2012) | 1973-11-13 | 1973-11-13 | |
| CH1595373 | 1973-11-13 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5082064A JPS5082064A (en, 2012) | 1975-07-03 |
| JPS5910348B2 true JPS5910348B2 (ja) | 1984-03-08 |
Family
ID=4413305
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP49130917A Expired JPS5910348B2 (ja) | 1973-11-13 | 1974-11-13 | ハロゲン置換ベンゾイミダゾロン誘導体の製造方法 |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US3954790A (en, 2012) |
| JP (1) | JPS5910348B2 (en, 2012) |
| AR (1) | AR204111A1 (en, 2012) |
| AT (1) | AT337695B (en, 2012) |
| BE (1) | BE822049A (en, 2012) |
| CA (1) | CA1030543A (en, 2012) |
| CH (1) | CH583201A5 (en, 2012) |
| DD (1) | DD114948A5 (en, 2012) |
| DE (1) | DE2453326A1 (en, 2012) |
| ES (1) | ES431849A1 (en, 2012) |
| FR (1) | FR2250747B1 (en, 2012) |
| GB (1) | GB1481859A (en, 2012) |
| NL (1) | NL7414814A (en, 2012) |
| SE (1) | SE7412527L (en, 2012) |
| SU (1) | SU520915A3 (en, 2012) |
| ZA (1) | ZA747237B (en, 2012) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3830324A (en) * | 1973-08-20 | 1974-08-20 | Hydranautics | Transporter for heavy loads |
| AT343911B (de) * | 1975-03-17 | 1978-06-26 | Schmidt Oskar | Verfahren zur herstellung von polyurethan-elastomeren |
| US4139706A (en) * | 1975-10-27 | 1979-02-13 | Lim-Holding, S.A. | Novel poly(thio)ethers having terminal amino groups, a process for their production and their application |
| CH619455A5 (en, 2012) * | 1976-01-07 | 1980-09-30 | Ciba Geigy Ag | |
| US4161603A (en) * | 1976-05-12 | 1979-07-17 | Ciba-Geigy Corporation | Dicarboxylic acids and dicarboxylic acid esters containing a benzimidazolone radical |
| US4228281A (en) * | 1977-09-23 | 1980-10-14 | Ciba-Geigy Corporation | Dicarboxylic acids containing triazine rings |
| CH640548A5 (de) * | 1979-08-28 | 1984-01-13 | Ciba Geigy Ag | Flammwidrige kunststofformmasse. |
| EP0043347A1 (de) * | 1980-06-26 | 1982-01-06 | Ciba-Geigy Ag | Halogenhaltige Benzimidazolonbisglycide und ihre Verwendung |
| US4341693A (en) * | 1980-06-26 | 1982-07-27 | Ciba-Geigy Corporation | Oligomeric epoxide resins and their use as flameproofing agents |
| MY145571A (en) | 2003-12-19 | 2012-02-29 | Ciba Holding Inc | Fluorocarbon terminated oligo-and poly-carbonates as surface modifiers |
| CN101910295B (zh) | 2007-11-01 | 2012-08-29 | 陶氏环球技术有限责任公司 | 原位湿气生成和用于硅烷-官能化树脂交联的多官能醇的使用 |
| EP3409707A1 (en) | 2017-05-30 | 2018-12-05 | Henkel AG & Co. KGaA | Method for producing functionalized polyesters |
| CN108395526B (zh) * | 2018-02-09 | 2020-03-10 | 四川大学 | 基于苯并咪唑结构的阻燃抗熔滴共聚酯及其制备方法 |
| CN111138633B (zh) * | 2020-01-07 | 2021-03-30 | 厦门大学 | 一种生物质本征阻燃耐高温环氧树脂及其制备方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3024166A (en) * | 1960-03-22 | 1962-03-06 | Bristol Myers Co | Analgesic dihydroxymethylbenzimidazol-2-ones |
| BE627013A (en, 2012) * | 1962-01-11 | |||
| BE793659A (fr) * | 1972-01-05 | 1973-07-04 | Ciba Geigy | Diglycidylimidazolidones et melanges durcissables qui en renferment |
-
1973
- 1973-11-13 CH CH1595373A patent/CH583201A5/xx not_active IP Right Cessation
-
1974
- 1974-01-01 AR AR256480A patent/AR204111A1/es active
- 1974-10-04 SE SE7412527A patent/SE7412527L/xx unknown
- 1974-11-05 US US05/521,228 patent/US3954790A/en not_active Expired - Lifetime
- 1974-11-08 CA CA213,317A patent/CA1030543A/en not_active Expired
- 1974-11-11 DE DE19742453326 patent/DE2453326A1/de active Granted
- 1974-11-11 DD DD182287A patent/DD114948A5/xx unknown
- 1974-11-12 SU SU2073854A patent/SU520915A3/ru active
- 1974-11-12 AT AT904974A patent/AT337695B/de not_active IP Right Cessation
- 1974-11-12 ES ES431849A patent/ES431849A1/es not_active Expired
- 1974-11-12 BE BE150381A patent/BE822049A/xx not_active IP Right Cessation
- 1974-11-12 ZA ZA00747237A patent/ZA747237B/xx unknown
- 1974-11-13 FR FR7437392A patent/FR2250747B1/fr not_active Expired
- 1974-11-13 NL NL7414814A patent/NL7414814A/xx not_active Application Discontinuation
- 1974-11-13 GB GB49203/74A patent/GB1481859A/en not_active Expired
- 1974-11-13 JP JP49130917A patent/JPS5910348B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE2453326C2 (en, 2012) | 1987-06-25 |
| DE2453326A1 (de) | 1975-05-15 |
| CA1030543A (en) | 1978-05-02 |
| CH583201A5 (en, 2012) | 1976-12-31 |
| ZA747237B (en) | 1975-11-26 |
| SE7412527L (en, 2012) | 1975-05-14 |
| GB1481859A (en) | 1977-08-03 |
| SU520915A3 (ru) | 1976-07-05 |
| BE822049A (fr) | 1975-05-12 |
| ATA904974A (de) | 1976-11-15 |
| AR204111A1 (es) | 1975-11-20 |
| US3954790A (en) | 1976-05-04 |
| NL7414814A (nl) | 1975-05-15 |
| FR2250747A1 (en, 2012) | 1975-06-06 |
| ES431849A1 (es) | 1976-11-01 |
| FR2250747B1 (en, 2012) | 1977-10-21 |
| AT337695B (de) | 1977-07-11 |
| JPS5082064A (en, 2012) | 1975-07-03 |
| DD114948A5 (en, 2012) | 1975-09-05 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPS5910348B2 (ja) | ハロゲン置換ベンゾイミダゾロン誘導体の製造方法 | |
| Lewis | Methylphenylpolysiloxanes | |
| JP2825532B2 (ja) | ビスイミド難燃剤製品の製造法 | |
| JPH0148911B2 (en, 2012) | ||
| JPS6322540A (ja) | ４−ハイドロキシフエニル４−ハイドロキシベンゾエ−トの製法 | |
| Maeda et al. | The synthetic intermediate of pyridoxine. I. A novel synthesis of 5-Alkoxy-2-carboxy-4-methyloxazole | |
| JP2636042B2 (ja) | ４，４▲′′′▼―ジヒドロキシクォーターフェニル誘導体およびその製造方法 | |
| JPH0586961B2 (en, 2012) | ||
| JPS6261586B2 (en, 2012) | ||
| CN109734642B (zh) | 萘酮-亚砜叶立德杂化体的合成及应用 | |
| US3341554A (en) | Process for preparing carboxylic acids | |
| DE3008902C2 (en, 2012) | ||
| US3254121A (en) | Bromination of salicylanilide | |
| CN100509751C (zh) | 苯并吡喃酮化合物的制备方法 | |
| JPH053857B2 (en, 2012) | ||
| JPS5910652B2 (ja) | 含フツ素フェニルベンゾエ−ト化合物およびその用途 | |
| CN101497571B (zh) | 苯并吡喃酮化合物的制备方法 | |
| JPS6053020B2 (ja) | ジカルボン酸及びジカルボン酸エステルならびにその製造法 | |
| JP3114244B2 (ja) | ソルビトール誘導体 | |
| JPS6244538B2 (en, 2012) | ||
| US3994865A (en) | Flame-resistant fibers of linear, thermoplastic polyesters | |
| Hussey et al. | a New Cyclic Azoxy Compound | |
| SU1101442A1 (ru) | Способ получени 10 @ -стирилпиримидо /1,2- @ /индол-2-онов | |
| US3217003A (en) | Method for preparing triaryl isocyanurates | |
| CA1254228A (en) | Method of producing the p-chlorophenol ester of p- chlorophenoxyisobutyric acid |