NO120270B - - Google Patents
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- Publication number
- NO120270B NO120270B NO162956A NO16295666A NO120270B NO 120270 B NO120270 B NO 120270B NO 162956 A NO162956 A NO 162956A NO 16295666 A NO16295666 A NO 16295666A NO 120270 B NO120270 B NO 120270B
- Authority
- NO
- Norway
- Prior art keywords
- benzofuran
- ethyl
- hydroxy
- dimethyl
- solution
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 29
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 239000002253 acid Substances 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 13
- 150000001907 coumarones Chemical class 0.000 claims description 10
- 150000002118 epoxides Chemical class 0.000 claims description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 3
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 159
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 127
- 239000000243 solution Substances 0.000 description 105
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 68
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 57
- 239000000203 mixture Substances 0.000 description 57
- 235000019441 ethanol Nutrition 0.000 description 54
- 238000002844 melting Methods 0.000 description 54
- 230000008018 melting Effects 0.000 description 54
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 52
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 51
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 44
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 37
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
- 238000001704 evaporation Methods 0.000 description 29
- 239000000706 filtrate Substances 0.000 description 28
- 230000008020 evaporation Effects 0.000 description 26
- 238000006243 chemical reaction Methods 0.000 description 24
- 238000002425 crystallisation Methods 0.000 description 24
- 230000008025 crystallization Effects 0.000 description 24
- 238000003756 stirring Methods 0.000 description 24
- 239000011541 reaction mixture Substances 0.000 description 22
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 238000009835 boiling Methods 0.000 description 21
- 239000003054 catalyst Substances 0.000 description 21
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 21
- 239000000284 extract Substances 0.000 description 18
- 238000010992 reflux Methods 0.000 description 18
- 229910052739 hydrogen Inorganic materials 0.000 description 17
- 239000001257 hydrogen Substances 0.000 description 17
- 239000002904 solvent Substances 0.000 description 17
- 239000007858 starting material Substances 0.000 description 17
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 16
- 229910052938 sodium sulfate Inorganic materials 0.000 description 16
- 235000011152 sodium sulphate Nutrition 0.000 description 16
- 150000001412 amines Chemical class 0.000 description 15
- 239000002585 base Substances 0.000 description 15
- 239000013078 crystal Substances 0.000 description 15
- -1 halogen ketones Chemical class 0.000 description 15
- 239000003208 petroleum Substances 0.000 description 14
- 239000002244 precipitate Substances 0.000 description 14
- 239000000047 product Substances 0.000 description 14
- 238000001953 recrystallisation Methods 0.000 description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 13
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 13
- 238000006467 substitution reaction Methods 0.000 description 13
- 238000001816 cooling Methods 0.000 description 11
- 150000003944 halohydrins Chemical class 0.000 description 11
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- BULLHNJGPPOUOX-UHFFFAOYSA-N chloroacetone Chemical compound CC(=O)CCl BULLHNJGPPOUOX-UHFFFAOYSA-N 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- 239000012074 organic phase Substances 0.000 description 8
- 229910000029 sodium carbonate Inorganic materials 0.000 description 8
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 8
- 238000010521 absorption reaction Methods 0.000 description 7
- 239000008346 aqueous phase Substances 0.000 description 7
- 239000012279 sodium borohydride Substances 0.000 description 7
- 229910000033 sodium borohydride Inorganic materials 0.000 description 7
- 235000011121 sodium hydroxide Nutrition 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 239000012259 ether extract Substances 0.000 description 6
- 239000005457 ice water Substances 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical class OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 description 6
- XTMVMVOXQSVHBW-UHFFFAOYSA-N 2-chloro-1-(5,6-dimethyl-1-benzofuran-2-yl)ethanol Chemical compound ClCC(O)C=1OC2=C(C1)C=C(C(=C2)C)C XTMVMVOXQSVHBW-UHFFFAOYSA-N 0.000 description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 5
- 125000001246 bromo group Chemical group Br* 0.000 description 5
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 230000036571 hydration Effects 0.000 description 5
- 238000006703 hydration reaction Methods 0.000 description 5
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 4
- OYKIBHHCEGIIMB-UHFFFAOYSA-N 1-(5-bromo-6,7-dimethyl-1-benzofuran-2-yl)-2-(propan-2-ylamino)ethanol Chemical compound BrC=1C(=C(C2=C(C=C(O2)C(CNC(C)C)O)C1)C)C OYKIBHHCEGIIMB-UHFFFAOYSA-N 0.000 description 4
- LVKCLVNWQTUVEK-UHFFFAOYSA-N 1-(6,7-dimethyl-1-benzofuran-2-yl)-2-(propan-2-ylamino)ethanol Chemical compound C1=C(C)C(C)=C2OC(C(O)CNC(C)C)=CC2=C1 LVKCLVNWQTUVEK-UHFFFAOYSA-N 0.000 description 4
- VGKNWJLKWJUBCQ-UHFFFAOYSA-N 2-chloro-1-(6,7-dimethyl-1-benzofuran-2-yl)ethanol Chemical compound ClCC(O)C=1OC2=C(C1)C=CC(=C2C)C VGKNWJLKWJUBCQ-UHFFFAOYSA-N 0.000 description 4
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 4
- SFHHSTAPEXMOJY-UHFFFAOYSA-N BrC=1C=C(C2=C(C=C(O2)C(CNC(C)C)O)C1)C Chemical compound BrC=1C=C(C2=C(C=C(O2)C(CNC(C)C)O)C1)C SFHHSTAPEXMOJY-UHFFFAOYSA-N 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 239000011230 binding agent Substances 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 239000012458 free base Substances 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002431 hydrogen Chemical class 0.000 description 4
- 239000000155 melt Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- ITRZLPYZRBRYJM-UHFFFAOYSA-N 1-(5,6-dimethyl-1-benzofuran-2-yl)-2-(propan-2-ylamino)ethanol Chemical compound C(C)(C)NCC(O)C=1OC2=C(C1)C=C(C(=C2)C)C ITRZLPYZRBRYJM-UHFFFAOYSA-N 0.000 description 3
- IGXOMTVOOXTCKI-UHFFFAOYSA-N 1-(5,6-dimethyl-1-benzofuran-2-yl)ethanone Chemical compound CC1=C(C)C=C2OC(C(=O)C)=CC2=C1 IGXOMTVOOXTCKI-UHFFFAOYSA-N 0.000 description 3
- NTSDVXMQZZWWQY-UHFFFAOYSA-N 1-(5,7-dimethyl-1-benzofuran-2-yl)ethanone Chemical compound CC1=CC(C)=C2OC(C(=O)C)=CC2=C1 NTSDVXMQZZWWQY-UHFFFAOYSA-N 0.000 description 3
- XGJLQDGUVDNLPL-UHFFFAOYSA-N 1-(5-bromo-6,7-dimethyl-1-benzofuran-2-yl)-2-chloroethanone Chemical compound ClCC(=O)C=1OC2=C(C1)C=C(C(=C2C)C)Br XGJLQDGUVDNLPL-UHFFFAOYSA-N 0.000 description 3
- GNPKVYPZSGCARR-UHFFFAOYSA-N 1-(5-bromo-6,7-dimethyl-1-benzofuran-2-yl)ethanone Chemical compound BrC1=C(C)C(C)=C2OC(C(=O)C)=CC2=C1 GNPKVYPZSGCARR-UHFFFAOYSA-N 0.000 description 3
- HBEDSQVIWPRPAY-UHFFFAOYSA-N 2,3-dihydrobenzofuran Chemical compound C1=CC=C2OCCC2=C1 HBEDSQVIWPRPAY-UHFFFAOYSA-N 0.000 description 3
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 3
- HVMZMVHWPRHHDE-UHFFFAOYSA-N 2-(5,6-dimethyl-1-benzofuran-2-yl)-2-(propan-2-ylamino)ethanol Chemical compound C(C)(C)NC(CO)C=1OC2=C(C1)C=C(C(=C2)C)C HVMZMVHWPRHHDE-UHFFFAOYSA-N 0.000 description 3
- CPUSIIHQFLWFKM-UHFFFAOYSA-N 2-chloro-1-(4,6-dimethyl-1-benzofuran-2-yl)ethanol Chemical compound ClCC(O)C=1OC2=C(C1)C(=CC(=C2)C)C CPUSIIHQFLWFKM-UHFFFAOYSA-N 0.000 description 3
- RIRHQYANMDJHLJ-UHFFFAOYSA-N 2-chloro-1-(4,6-dimethyl-1-benzofuran-2-yl)ethanone Chemical compound ClCC(=O)C=1OC2=C(C1)C(=CC(=C2)C)C RIRHQYANMDJHLJ-UHFFFAOYSA-N 0.000 description 3
- HGKFMPRYPNPXGN-UHFFFAOYSA-N 2-chloro-1-(5,6-dimethyl-1-benzofuran-2-yl)ethanone Chemical compound ClCC(=O)C=1OC2=C(C1)C=C(C(=C2)C)C HGKFMPRYPNPXGN-UHFFFAOYSA-N 0.000 description 3
- IBIAQTGIWQGGNF-UHFFFAOYSA-N 2-chloro-1-(5,7-dimethyl-1-benzofuran-2-yl)ethanone Chemical compound ClCC(=O)C=1OC2=C(C1)C=C(C=C2C)C IBIAQTGIWQGGNF-UHFFFAOYSA-N 0.000 description 3
- QWROGFZFKWZDCJ-UHFFFAOYSA-N 2-chloro-1-(6,7-dimethyl-1-benzofuran-2-yl)ethanone Chemical compound ClCC(=O)C=1OC2=C(C1)C=CC(=C2C)C QWROGFZFKWZDCJ-UHFFFAOYSA-N 0.000 description 3
- JIILFJCSXPACCD-UHFFFAOYSA-N 2-chloro-1-(6-methyl-1-benzofuran-2-yl)ethanone Chemical compound ClCC(=O)C=1OC2=C(C1)C=CC(=C2)C JIILFJCSXPACCD-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- BBYKUCRQWTUDOX-UHFFFAOYSA-N ClCC(O)C=1OC2=C(C1)C=CC(=C2)C Chemical compound ClCC(O)C=1OC2=C(C1)C=CC(=C2)C BBYKUCRQWTUDOX-UHFFFAOYSA-N 0.000 description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000001640 fractional crystallisation Methods 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 238000004809 thin layer chromatography Methods 0.000 description 3
- BREYSFXKCAYTPG-UHFFFAOYSA-N 1-(5,6-dimethyl-1-benzofuran-2-yl)-2-(propan-2-ylamino)ethanol hydrochloride Chemical compound Cl.C(C)(C)NCC(O)C=1OC2=C(C1)C=C(C(=C2)C)C BREYSFXKCAYTPG-UHFFFAOYSA-N 0.000 description 2
- POYHXKYRBLUBDP-UHFFFAOYSA-N 1-(5,7-dibromo-4-methyl-1-benzofuran-2-yl)-2-(propan-2-ylamino)ethanol Chemical compound BrC=1C=C(C2=C(C=C(O2)C(CNC(C)C)O)C1C)Br POYHXKYRBLUBDP-UHFFFAOYSA-N 0.000 description 2
- BBVPFZQONOONGZ-UHFFFAOYSA-N 1-(5-bromo-6,7-dimethyl-1-benzofuran-2-yl)-2-chloroethanol Chemical compound BrC=1C(=C(C2=C(C=C(O2)C(CCl)O)C1)C)C BBVPFZQONOONGZ-UHFFFAOYSA-N 0.000 description 2
- MFYPMFVGBNFZBL-UHFFFAOYSA-N 1-(5-bromo-7-ethyl-1-benzofuran-2-yl)-2-(propan-2-ylamino)ethanol Chemical compound BrC=1C=C(C2=C(C=C(O2)C(CNC(C)C)O)C1)CC MFYPMFVGBNFZBL-UHFFFAOYSA-N 0.000 description 2
- GPOBDLAUCDZDIJ-UHFFFAOYSA-N 1-(5-bromo-7-ethyl-1-benzofuran-2-yl)-2-chloroethanol Chemical compound CCC1=CC(Br)=CC2=C1OC(C(O)CCl)=C2 GPOBDLAUCDZDIJ-UHFFFAOYSA-N 0.000 description 2
- VJNALHQRNMZYBD-UHFFFAOYSA-N 1-(5-bromo-7-methyl-1-benzofuran-2-yl)-2-chloroethanol Chemical compound BrC=1C=C(C2=C(C=C(O2)C(CCl)O)C1)C VJNALHQRNMZYBD-UHFFFAOYSA-N 0.000 description 2
- KQDCMQDWSNQPOI-UHFFFAOYSA-N 1-(5-bromo-7-methyl-1-benzofuran-2-yl)-2-chloroethanone Chemical compound ClCC(=O)C=1OC2=C(C1)C=C(C=C2C)Br KQDCMQDWSNQPOI-UHFFFAOYSA-N 0.000 description 2
- KVPCRWUOWXALRM-UHFFFAOYSA-N 1-(5-bromo-7-methyl-1-benzofuran-2-yl)ethanone Chemical compound BrC1=CC(C)=C2OC(C(=O)C)=CC2=C1 KVPCRWUOWXALRM-UHFFFAOYSA-N 0.000 description 2
- NAZPOVYNILYBCJ-UHFFFAOYSA-N 1-(5-methyl-1-benzofuran-2-yl)-2-(propan-2-ylamino)ethanol Chemical compound C(C)(C)NCC(O)C=1OC2=C(C1)C=C(C=C2)C NAZPOVYNILYBCJ-UHFFFAOYSA-N 0.000 description 2
- FRROHJREDWNRNQ-UHFFFAOYSA-N 1-(6,7-dimethyl-1-benzofuran-2-yl)-2-(propan-2-ylamino)ethanol;hydrochloride Chemical compound Cl.C1=C(C)C(C)=C2OC(C(O)CNC(C)C)=CC2=C1 FRROHJREDWNRNQ-UHFFFAOYSA-N 0.000 description 2
- CSIYPFJAOMCHGE-UHFFFAOYSA-N 1-(6,7-dimethyl-1-benzofuran-2-yl)ethanone Chemical compound C1=C(C)C(C)=C2OC(C(=O)C)=CC2=C1 CSIYPFJAOMCHGE-UHFFFAOYSA-N 0.000 description 2
- ZPLPPHUAGUDZJM-UHFFFAOYSA-N 1-(6-methyl-1-benzofuran-2-yl)ethanone Chemical compound C1=C(C)C=C2OC(C(=O)C)=CC2=C1 ZPLPPHUAGUDZJM-UHFFFAOYSA-N 0.000 description 2
- NTEXLUACOZQFDO-UHFFFAOYSA-N 1-(7-ethyl-1-benzofuran-2-yl)-2-(propan-2-ylamino)ethanol Chemical compound C(C)(C)NCC(O)C=1OC2=C(C1)C=CC=C2CC NTEXLUACOZQFDO-UHFFFAOYSA-N 0.000 description 2
- JMMQCUYNPMNCPP-UHFFFAOYSA-N 1-(7-methyl-1-benzofuran-2-yl)-2-(propan-2-ylamino)ethanol Chemical compound C(C)(C)NCC(O)C=1OC2=C(C1)C=CC=C2C JMMQCUYNPMNCPP-UHFFFAOYSA-N 0.000 description 2
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
- JODRRPJMQDFCBJ-UHFFFAOYSA-N 2-Hydroxy-4-methylbenzaldehyde Chemical compound CC1=CC=C(C=O)C(O)=C1 JODRRPJMQDFCBJ-UHFFFAOYSA-N 0.000 description 2
- UNWVYWZPMKJMFJ-UHFFFAOYSA-N 2-chloro-1-(5,7-dimethyl-1-benzofuran-2-yl)ethanol Chemical compound ClCC(O)C=1OC2=C(C1)C=C(C=C2C)C UNWVYWZPMKJMFJ-UHFFFAOYSA-N 0.000 description 2
- OPIPPEZQABSGQE-UHFFFAOYSA-N 2-hydroxy-3,4-dimethylbenzaldehyde Chemical compound CC1=CC=C(C=O)C(O)=C1C OPIPPEZQABSGQE-UHFFFAOYSA-N 0.000 description 2
- PWFKERWVXUISSK-UHFFFAOYSA-N 2-hydroxy-4,5-dimethylbenzaldehyde Chemical compound CC1=CC(O)=C(C=O)C=C1C PWFKERWVXUISSK-UHFFFAOYSA-N 0.000 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
- XXJJCJVBSMEQTQ-UHFFFAOYSA-N 5-bromo-2-hydroxy-3,4-dimethylbenzaldehyde Chemical compound CC1=C(C)C(O)=C(C=O)C=C1Br XXJJCJVBSMEQTQ-UHFFFAOYSA-N 0.000 description 2
- RKAGPBANPHKVKS-UHFFFAOYSA-N BrC1=CC(=CC=2C=C(OC21)C(CNC(C)C)O)C Chemical compound BrC1=CC(=CC=2C=C(OC21)C(CNC(C)C)O)C RKAGPBANPHKVKS-UHFFFAOYSA-N 0.000 description 2
- YFZFHBPMOFVDNZ-UHFFFAOYSA-N Cl.BrC=1C=C(C2=C(C=C(O2)C(CNC(C)C)O)C1)C Chemical compound Cl.BrC=1C=C(C2=C(C=C(O2)C(CNC(C)C)O)C1)C YFZFHBPMOFVDNZ-UHFFFAOYSA-N 0.000 description 2
- 239000005909 Kieselgur Substances 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000005660 chlorination reaction Methods 0.000 description 2
- 239000002026 chloroform extract Substances 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- QTMDXZNDVAMKGV-UHFFFAOYSA-L copper(ii) bromide Chemical compound [Cu+2].[Br-].[Br-] QTMDXZNDVAMKGV-UHFFFAOYSA-L 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 238000006704 dehydrohalogenation reaction Methods 0.000 description 2
- 125000005283 haloketone group Chemical group 0.000 description 2
- 150000004677 hydrates Chemical class 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 2
- 238000004611 spectroscopical analysis Methods 0.000 description 2
- 230000001975 sympathomimetic effect Effects 0.000 description 2
- YUTFQTAITWWGFH-UHFFFAOYSA-N 1-(1-benzofuran-2-yl)ethanone Chemical class C1=CC=C2OC(C(=O)C)=CC2=C1 YUTFQTAITWWGFH-UHFFFAOYSA-N 0.000 description 1
- VOMFDTVNNBWNBT-UHFFFAOYSA-N 1-(4,6-dimethyl-1-benzofuran-2-yl)ethanone Chemical compound C1=C(C)C=C2OC(C(=O)C)=CC2=C1C VOMFDTVNNBWNBT-UHFFFAOYSA-N 0.000 description 1
- MTMLZAYSWCXUAR-UHFFFAOYSA-N 1-(4-methyl-1-benzofuran-2-yl)-2-(propan-2-ylamino)ethanol Chemical compound C(C)(C)NCC(O)C=1OC2=C(C1)C(=CC=C2)C MTMLZAYSWCXUAR-UHFFFAOYSA-N 0.000 description 1
- OPANCVPQWHXMEV-UHFFFAOYSA-N 1-(4-methyl-1-benzofuran-2-yl)-2-(propan-2-ylamino)ethanol hydrochloride Chemical compound Cl.C(C)(C)NCC(O)C=1OC2=C(C1)C(=CC=C2)C OPANCVPQWHXMEV-UHFFFAOYSA-N 0.000 description 1
- SYSQCQYOHVPKJZ-UHFFFAOYSA-N 1-(5-bromo-7-ethyl-1-benzofuran-2-yl)-2-chloroethanone Chemical compound CCC1=CC(Br)=CC2=C1OC(C(=O)CCl)=C2 SYSQCQYOHVPKJZ-UHFFFAOYSA-N 0.000 description 1
- YIRBVIWNQRNALH-UHFFFAOYSA-N 1-(6-methyl-1-benzofuran-2-yl)-2-(propan-2-ylamino)ethanol hydrochloride Chemical compound Cl.C(C)(C)NCC(O)C=1OC2=C(C1)C=CC(=C2)C YIRBVIWNQRNALH-UHFFFAOYSA-N 0.000 description 1
- GFSNTXHGIWNXSO-UHFFFAOYSA-N 1-(7-bromo-5-methyl-1-benzofuran-2-yl)-2-chloroethanol Chemical compound BrC1=CC(=CC=2C=C(OC21)C(CCl)O)C GFSNTXHGIWNXSO-UHFFFAOYSA-N 0.000 description 1
- BOPAZEJKRKUDOB-UHFFFAOYSA-N 1-(7-bromo-5-methyl-1-benzofuran-2-yl)-2-chloroethanone Chemical compound ClCC(=O)C=1OC2=C(C1)C=C(C=C2Br)C BOPAZEJKRKUDOB-UHFFFAOYSA-N 0.000 description 1
- JKTCBAGSMQIFNL-UHFFFAOYSA-N 2,3-dihydrofuran Chemical class C1CC=CO1 JKTCBAGSMQIFNL-UHFFFAOYSA-N 0.000 description 1
- USDOODPXGRUISP-UHFFFAOYSA-N 2-(6,7-dimethyl-1-benzofuran-2-yl)-2-(propan-2-ylamino)ethanol hydrochloride Chemical compound Cl.C(C)(C)NC(CO)C=1OC2=C(C1)C=CC(=C2C)C USDOODPXGRUISP-UHFFFAOYSA-N 0.000 description 1
- WFPCMJHBLODESX-UHFFFAOYSA-N 2-(propan-2-ylamino)-1-(7-propyl-1-benzofuran-2-yl)ethanol hydrochloride Chemical compound Cl.C(C)(C)NCC(O)C=1OC2=C(C1)C=CC=C2CCC WFPCMJHBLODESX-UHFFFAOYSA-N 0.000 description 1
- DIHSPKQKRICOIF-UHFFFAOYSA-N 2-chloro-1-(5,7-dibromo-4-methyl-1-benzofuran-2-yl)ethanol Chemical compound BrC=1C=C(C2=C(C=C(O2)C(CCl)O)C1C)Br DIHSPKQKRICOIF-UHFFFAOYSA-N 0.000 description 1
- FOMREEXNIYICSK-UHFFFAOYSA-N 2-chloro-1-(5,7-dibromo-4-methyl-1-benzofuran-2-yl)ethanone Chemical compound ClCC(=O)C=1OC2=C(C1)C(=C(C=C2Br)Br)C FOMREEXNIYICSK-UHFFFAOYSA-N 0.000 description 1
- JDWLZCFMLFLSNE-UHFFFAOYSA-N 2-chloro-1-(7-ethyl-1-benzofuran-2-yl)ethanol Chemical compound CCC1=CC=CC2=C1OC(C(O)CCl)=C2 JDWLZCFMLFLSNE-UHFFFAOYSA-N 0.000 description 1
- DSXKMMAQDSAZAC-UHFFFAOYSA-N 2-hydroxy-3,5-dimethylbenzaldehyde Chemical compound CC1=CC(C)=C(O)C(C=O)=C1 DSXKMMAQDSAZAC-UHFFFAOYSA-N 0.000 description 1
- QVNGLKIFRNFPQC-UHFFFAOYSA-N 2-hydroxy-4,6-dimethylbenzaldehyde Chemical compound CC1=CC(C)=C(C=O)C(O)=C1 QVNGLKIFRNFPQC-UHFFFAOYSA-N 0.000 description 1
- PZGFSVYPDAQKHJ-UHFFFAOYSA-N 5-bromo-2-hydroxy-3-methylbenzaldehyde Chemical compound CC1=CC(Br)=CC(C=O)=C1O PZGFSVYPDAQKHJ-UHFFFAOYSA-N 0.000 description 1
- 206010002383 Angina Pectoris Diseases 0.000 description 1
- ZLDBJGPGMCEEOK-UHFFFAOYSA-N C(C)(C)NCC(O)C1OC2=C(C1)C=CC(=C2C)C Chemical compound C(C)(C)NCC(O)C1OC2=C(C1)C=CC(=C2C)C ZLDBJGPGMCEEOK-UHFFFAOYSA-N 0.000 description 1
- SWPSUMYSSQCJAT-UHFFFAOYSA-N Cl.C(C)(C)NCC(O)C1OC2=C(C1)C=C(C(=C2)C)C Chemical compound Cl.C(C)(C)NCC(O)C1OC2=C(C1)C=C(C(=C2)C)C SWPSUMYSSQCJAT-UHFFFAOYSA-N 0.000 description 1
- WTANIDXGCYIKQJ-UHFFFAOYSA-N Cl.C(C)(C)NCC(O)C=1OC2=C(C1)C=C(C=C2CCC)C Chemical compound Cl.C(C)(C)NCC(O)C=1OC2=C(C1)C=C(C=C2CCC)C WTANIDXGCYIKQJ-UHFFFAOYSA-N 0.000 description 1
- SACBAIHMGPAAHD-UHFFFAOYSA-N Cl.C(C)(C)NCC(O)C=1OC2=C(C1)C=C(C=C2CCC)CCC Chemical compound Cl.C(C)(C)NCC(O)C=1OC2=C(C1)C=C(C=C2CCC)CCC SACBAIHMGPAAHD-UHFFFAOYSA-N 0.000 description 1
- 229910021590 Copper(II) bromide Inorganic materials 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 239000006286 aqueous extract Substances 0.000 description 1
- 206010003119 arrhythmia Diseases 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- VXAOKODLROCQJS-UHFFFAOYSA-N furan;hydrochloride Chemical compound Cl.C=1C=COC=1 VXAOKODLROCQJS-UHFFFAOYSA-N 0.000 description 1
- 208000019622 heart disease Diseases 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000013081 microcrystal Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- NIXKBAZVOQAHGC-UHFFFAOYSA-N phenylmethanesulfonic acid Chemical class OS(=O)(=O)CC1=CC=CC=C1 NIXKBAZVOQAHGC-UHFFFAOYSA-N 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D307/81—Radicals substituted by nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D307/80—Radicals substituted by oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Furan Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB19823/65A GB1106057A (en) | 1965-05-11 | 1965-05-11 | Novel benzofuran derivatives and the manufacture thereof |
| GB5320865 | 1965-12-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO120270B true NO120270B (da) | 1970-09-28 |
Family
ID=26254274
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO162956A NO120270B (da) | 1965-05-11 | 1966-05-10 |
Country Status (12)
| Country | Link |
|---|---|
| BE (1) | BE680737A (da) |
| BR (1) | BR6679335D0 (da) |
| CH (3) | CH513146A (da) |
| DK (1) | DK123769B (da) |
| ES (1) | ES326559A1 (da) |
| FI (1) | FI45329C (da) |
| FR (1) | FR6011M (da) |
| GB (1) | GB1106057A (da) |
| IL (1) | IL25650A (da) |
| NL (1) | NL153541B (da) |
| NO (1) | NO120270B (da) |
| SE (1) | SE326196B (da) |
-
1965
- 1965-05-11 GB GB19823/65A patent/GB1106057A/en not_active Expired
-
1966
- 1966-04-27 CH CH67270A patent/CH513146A/de not_active IP Right Cessation
- 1966-04-27 CH CH1749768A patent/CH498109A/de not_active IP Right Cessation
- 1966-04-27 CH CH610666A patent/CH468371A/de unknown
- 1966-04-28 IL IL25650A patent/IL25650A/xx unknown
- 1966-05-07 FR FR60695A patent/FR6011M/fr not_active Expired
- 1966-05-09 BE BE680737D patent/BE680737A/xx not_active IP Right Cessation
- 1966-05-09 BR BR179335/66A patent/BR6679335D0/pt unknown
- 1966-05-10 ES ES0326559A patent/ES326559A1/es not_active Expired
- 1966-05-10 NO NO162956A patent/NO120270B/no unknown
- 1966-05-11 SE SE06456/66A patent/SE326196B/xx unknown
- 1966-05-11 FI FI661245A patent/FI45329C/fi active
- 1966-05-11 DK DK241366AA patent/DK123769B/da unknown
- 1966-05-11 NL NL666606441A patent/NL153541B/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CH468371A (de) | 1969-02-15 |
| CH513146A (de) | 1971-09-30 |
| IL25650A (en) | 1969-11-30 |
| GB1106057A (en) | 1968-03-13 |
| DE1543653B2 (de) | 1975-06-05 |
| FI45329C (fi) | 1972-05-10 |
| SE326196B (da) | 1970-07-20 |
| FR6011M (da) | 1968-05-06 |
| ES326559A1 (es) | 1967-03-01 |
| BR6679335D0 (pt) | 1973-10-23 |
| FI45329B (da) | 1972-01-31 |
| NL6606441A (da) | 1966-11-14 |
| CH498109A (de) | 1970-10-31 |
| DK123769B (da) | 1972-07-31 |
| DE1543653A1 (de) | 1969-09-18 |
| BE680737A (da) | 1966-11-09 |
| NL153541B (nl) | 1977-06-15 |
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