NO771422L - Fremgangsm}te for fremstilling av tetramisol, levamisol og derivater derav - Google Patents
Fremgangsm}te for fremstilling av tetramisol, levamisol og derivater deravInfo
- Publication number
- NO771422L NO771422L NO771422A NO771422A NO771422L NO 771422 L NO771422 L NO 771422L NO 771422 A NO771422 A NO 771422A NO 771422 A NO771422 A NO 771422A NO 771422 L NO771422 L NO 771422L
- Authority
- NO
- Norway
- Prior art keywords
- phenyl
- methoxyethyl
- formula
- imidazolidone
- imidazolin
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 24
- 238000002360 preparation method Methods 0.000 title claims description 13
- HLFSDGLLUJUHTE-SNVBAGLBSA-N Levamisole Chemical compound C1([C@H]2CN3CCSC3=N2)=CC=CC=C1 HLFSDGLLUJUHTE-SNVBAGLBSA-N 0.000 title description 10
- 229960001614 levamisole Drugs 0.000 title description 9
- 150000001875 compounds Chemical class 0.000 claims description 46
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 27
- 239000002904 solvent Substances 0.000 claims description 25
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 19
- -1 acyl anhydride Chemical class 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 15
- 239000003054 catalyst Substances 0.000 claims description 15
- CAAMSDWKXXPUJR-UHFFFAOYSA-N 3,5-dihydro-4H-imidazol-4-one Chemical class O=C1CNC=N1 CAAMSDWKXXPUJR-UHFFFAOYSA-N 0.000 claims description 11
- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 claims description 9
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 8
- GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 239000011593 sulfur Substances 0.000 claims description 7
- UXERCGOLBABXTB-UHFFFAOYSA-N 3-(2-methoxyethyl)-5-phenyl-1h-imidazol-2-one Chemical compound N1C(=O)N(CCOC)C=C1C1=CC=CC=C1 UXERCGOLBABXTB-UHFFFAOYSA-N 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- 239000003153 chemical reaction reagent Substances 0.000 claims description 5
- 150000002431 hydrogen Chemical group 0.000 claims description 5
- 238000005984 hydrogenation reaction Methods 0.000 claims description 5
- 239000012434 nucleophilic reagent Substances 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- JHALJJCMBMHOMB-UHFFFAOYSA-N 1-(2-hydroxyethyl)-4-phenylimidazolidin-2-one Chemical compound N1C(=O)N(CCO)CC1C1=CC=CC=C1 JHALJJCMBMHOMB-UHFFFAOYSA-N 0.000 claims description 4
- SAUCUHKFBAYUJF-UHFFFAOYSA-N 2-(2-oxo-4-phenylimidazolidin-1-yl)ethyl acetate Chemical compound N1C(=O)N(CCOC(=O)C)CC1C1=CC=CC=C1 SAUCUHKFBAYUJF-UHFFFAOYSA-N 0.000 claims description 4
- IMLSCHKGHPZCRB-UHFFFAOYSA-N 2-(2-oxo-5-phenyl-1h-imidazol-3-yl)ethyl acetate Chemical compound N1C(=O)N(CCOC(=O)C)C=C1C1=CC=CC=C1 IMLSCHKGHPZCRB-UHFFFAOYSA-N 0.000 claims description 4
- 239000004215 Carbon black (E152) Substances 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- XLJMAIOERFSOGZ-UHFFFAOYSA-N cyanic acid Chemical compound OC#N XLJMAIOERFSOGZ-UHFFFAOYSA-N 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 4
- XJDMWEBCUKGNMW-UHFFFAOYSA-N 3-(2-butoxyethyl)-5-phenyl-1h-imidazol-2-one Chemical compound N1C(=O)N(CCOCCCC)C=C1C1=CC=CC=C1 XJDMWEBCUKGNMW-UHFFFAOYSA-N 0.000 claims description 3
- DYXLJVBGQMMTHR-UHFFFAOYSA-N 3-acetyl-1-(2-methoxyethyl)-4-phenylimidazol-2-one Chemical compound CC(=O)N1C(=O)N(CCOC)C=C1C1=CC=CC=C1 DYXLJVBGQMMTHR-UHFFFAOYSA-N 0.000 claims description 3
- BVHHMHMXFWJGOF-UHFFFAOYSA-N 3-acetyl-1-(2-methoxyethyl)-4-phenylimidazolidin-2-one Chemical compound CC(=O)N1C(=O)N(CCOC)CC1C1=CC=CC=C1 BVHHMHMXFWJGOF-UHFFFAOYSA-N 0.000 claims description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 239000012458 free base Substances 0.000 claims description 3
- 229930195733 hydrocarbon Natural products 0.000 claims description 3
- 150000002430 hydrocarbons Chemical class 0.000 claims description 3
- 238000010992 reflux Methods 0.000 claims description 3
- HAHTWNTVJQGVLH-UHFFFAOYSA-N 1-(2-butoxyethyl)-4-phenylimidazolidin-2-one Chemical compound N1C(=O)N(CCOCCCC)CC1C1=CC=CC=C1 HAHTWNTVJQGVLH-UHFFFAOYSA-N 0.000 claims description 2
- CALKKCCPRZLOLZ-UHFFFAOYSA-N 1-(2-methoxyethyl)-4-(3-methoxyphenyl)imidazolidin-2-one Chemical compound N1C(=O)N(CCOC)CC1C1=CC=CC(OC)=C1 CALKKCCPRZLOLZ-UHFFFAOYSA-N 0.000 claims description 2
- COHVXEPINWPACP-UHFFFAOYSA-N 2-(2-oxo-4-phenylimidazolidin-1-yl)ethyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCCN(C(N1)=O)CC1C1=CC=CC=C1 COHVXEPINWPACP-UHFFFAOYSA-N 0.000 claims description 2
- MGGQHZLAIXIXRO-UHFFFAOYSA-N 3-(2-methoxybenzoyl)-1-(2-methoxyethyl)-4-phenylimidazol-2-one Chemical compound C=1C=CC=C(OC)C=1C(=O)N1C(=O)N(CCOC)C=C1C1=CC=CC=C1 MGGQHZLAIXIXRO-UHFFFAOYSA-N 0.000 claims description 2
- JPJBBFTVJDPHBH-UHFFFAOYSA-N 3-(adamantane-1-carbonyl)-1-(2-methoxyethyl)-4-phenylimidazol-2-one Chemical compound C1C(C2)CC(C3)CC2CC13C(=O)N1C(=O)N(CCOC)C=C1C1=CC=CC=C1 JPJBBFTVJDPHBH-UHFFFAOYSA-N 0.000 claims description 2
- GRKCNKCWEWUOAB-UHFFFAOYSA-N 3-(adamantane-1-carbonyl)-1-(2-methoxyethyl)-4-phenylimidazolidin-2-one Chemical compound C1C(C2)CC(C3)CC2CC13C(=O)N1C(=O)N(CCOC)CC1C1=CC=CC=C1 GRKCNKCWEWUOAB-UHFFFAOYSA-N 0.000 claims description 2
- IWEKDEBYEUTNSR-UHFFFAOYSA-N 3-(cyclohexanecarbonyl)-1-(2-methoxyethyl)-4-phenylimidazol-2-one Chemical compound C1CCCCC1C(=O)N1C(=O)N(CCOC)C=C1C1=CC=CC=C1 IWEKDEBYEUTNSR-UHFFFAOYSA-N 0.000 claims description 2
- WUUSKKYXRAMVAT-UHFFFAOYSA-N 3-(cyclohexanecarbonyl)-1-(2-methoxyethyl)-4-phenylimidazolidin-2-one Chemical compound O=C1N(CCOC)CC(C=2C=CC=CC=2)N1C(=O)C1CCCCC1 WUUSKKYXRAMVAT-UHFFFAOYSA-N 0.000 claims description 2
- MZUSRFLDXOQVIK-UHFFFAOYSA-N 3-benzoyl-1-(2-methoxyethyl)-4-phenylimidazolidin-2-one Chemical compound O=C1N(CCOC)CC(C=2C=CC=CC=2)N1C(=O)C1=CC=CC=C1 MZUSRFLDXOQVIK-UHFFFAOYSA-N 0.000 claims description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 150000001266 acyl halides Chemical class 0.000 claims description 2
- 150000001450 anions Chemical class 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 239000011630 iodine Substances 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-O oxonium Chemical compound [OH3+] XLYOFNOQVPJJNP-UHFFFAOYSA-O 0.000 claims description 2
- 229910052763 palladium Inorganic materials 0.000 claims description 2
- 229910052697 platinum Inorganic materials 0.000 claims description 2
- 150000003512 tertiary amines Chemical class 0.000 claims description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- CCPSXQZBFJNUQC-UHFFFAOYSA-N 1-(2-butoxyethyl)-4-phenylimidazolidine-2-thione Chemical compound N1C(=S)N(CCOCCCC)CC1C1=CC=CC=C1 CCPSXQZBFJNUQC-UHFFFAOYSA-N 0.000 claims 1
- LYLHYXVUJHVIEQ-UHFFFAOYSA-N 1-(2-methoxyethyl)-4-phenyl-3-[4-(trifluoromethyl)benzoyl]imidazol-2-one Chemical compound C=1C=C(C(F)(F)F)C=CC=1C(=O)N1C(=O)N(CCOC)C=C1C1=CC=CC=C1 LYLHYXVUJHVIEQ-UHFFFAOYSA-N 0.000 claims 1
- YBIDGBUFMFZYSV-UHFFFAOYSA-N 1-(2-phenoxyethyl)-4-phenylimidazolidine-2-thione Chemical compound S=C1NC(C=2C=CC=CC=2)CN1CCOC1=CC=CC=C1 YBIDGBUFMFZYSV-UHFFFAOYSA-N 0.000 claims 1
- VOHOBUIFWGMDRU-UHFFFAOYSA-N 3-(2-methoxyethyl)-5-(3-methoxyphenyl)-1H-imidazol-2-one Chemical compound N1C(=O)N(CCOC)C=C1C1=CC=CC(OC)=C1 VOHOBUIFWGMDRU-UHFFFAOYSA-N 0.000 claims 1
- QFVAZQWRPGRERC-UHFFFAOYSA-N 3-acetyl-1-(2-butoxyethyl)-4-phenylimidazolidin-2-one Chemical compound CC(=O)N1C(=O)N(CCOCCCC)CC1C1=CC=CC=C1 QFVAZQWRPGRERC-UHFFFAOYSA-N 0.000 claims 1
- XGJZRQDBEJOXRY-UHFFFAOYSA-N 4-(3-bromophenyl)-1-(2-methoxyethyl)imidazolidin-2-one Chemical compound N1C(=O)N(CCOC)CC1C1=CC=CC(Br)=C1 XGJZRQDBEJOXRY-UHFFFAOYSA-N 0.000 claims 1
- IBSPMXQCGKUNEQ-UHFFFAOYSA-N 5-(3-bromophenyl)-3-(2-methoxyethyl)-1h-imidazol-2-one Chemical compound N1C(=O)N(CCOC)C=C1C1=CC=CC(Br)=C1 IBSPMXQCGKUNEQ-UHFFFAOYSA-N 0.000 claims 1
- 101150047265 COR2 gene Proteins 0.000 claims 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims 1
- 101100295741 Gallus gallus COR4 gene Proteins 0.000 claims 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims 1
- 101100467189 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) QCR2 gene Proteins 0.000 claims 1
- 239000005864 Sulphur Substances 0.000 claims 1
- 239000002585 base Substances 0.000 claims 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 claims 1
- 229910017052 cobalt Inorganic materials 0.000 claims 1
- 239000010941 cobalt Substances 0.000 claims 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 229910052741 iridium Inorganic materials 0.000 claims 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims 1
- 229910052759 nickel Inorganic materials 0.000 claims 1
- 229910052703 rhodium Inorganic materials 0.000 claims 1
- 239000010948 rhodium Substances 0.000 claims 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims 1
- 229910052707 ruthenium Inorganic materials 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 37
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 36
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- 239000007787 solid Substances 0.000 description 22
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 13
- 239000000203 mixture Substances 0.000 description 13
- 239000003921 oil Substances 0.000 description 13
- 239000012044 organic layer Substances 0.000 description 13
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 9
- 229960000583 acetic acid Drugs 0.000 description 9
- 239000000706 filtrate Substances 0.000 description 9
- LIGACIXOYTUXAW-UHFFFAOYSA-N phenacyl bromide Chemical compound BrCC(=O)C1=CC=CC=C1 LIGACIXOYTUXAW-UHFFFAOYSA-N 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- JHLUHSUKOPRKDY-UHFFFAOYSA-N 1-(2-methoxyethyl)-4-phenylimidazolidin-2-one Chemical compound N1C(=O)N(CCOC)CC1C1=CC=CC=C1 JHLUHSUKOPRKDY-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 238000006722 reduction reaction Methods 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- WDUKOZVBDZRNCC-UHFFFAOYSA-N 1-(2-methoxyethyl)-4-phenylimidazolidine-2-thione Chemical compound N1C(=S)N(CCOC)CC1C1=CC=CC=C1 WDUKOZVBDZRNCC-UHFFFAOYSA-N 0.000 description 3
- ASUDFOJKTJLAIK-UHFFFAOYSA-N 2-methoxyethanamine Chemical compound COCCN ASUDFOJKTJLAIK-UHFFFAOYSA-N 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- WZMHXRHBDLIRTR-UHFFFAOYSA-N 3-(2-hydroxyethyl)-5-phenyl-1h-imidazol-2-one Chemical compound N1C(=O)N(CCO)C=C1C1=CC=CC=C1 WZMHXRHBDLIRTR-UHFFFAOYSA-N 0.000 description 2
- YXYOJZOKGZFVJY-UHFFFAOYSA-N 3-benzoyl-1-(2-methoxyethyl)-4-phenylimidazol-2-one Chemical compound C=1C=CC=CC=1C(=O)N1C(=O)N(CCOC)C=C1C1=CC=CC=C1 YXYOJZOKGZFVJY-UHFFFAOYSA-N 0.000 description 2
- PDQAZBWRQCGBEV-UHFFFAOYSA-N Ethylenethiourea Chemical compound S=C1NCCN1 PDQAZBWRQCGBEV-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
- WIRUZQNBHNAMAB-UHFFFAOYSA-N benzene;cyclohexane Chemical compound C1CCCCC1.C1=CC=CC=C1 WIRUZQNBHNAMAB-UHFFFAOYSA-N 0.000 description 2
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 239000012230 colorless oil Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- UZUODNWWWUQRIR-UHFFFAOYSA-L disodium;3-aminonaphthalene-1,5-disulfonate Chemical compound [Na+].[Na+].C1=CC=C(S([O-])(=O)=O)C2=CC(N)=CC(S([O-])(=O)=O)=C21 UZUODNWWWUQRIR-UHFFFAOYSA-L 0.000 description 2
- 150000002169 ethanolamines Chemical class 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 238000001665 trituration Methods 0.000 description 2
- HCKXIENNWYVMBG-UHFFFAOYSA-N 1-(2-methoxyethyl)-3-(2-methylbenzoyl)-4-phenylimidazol-2-one Chemical compound C=1C=CC=C(C)C=1C(=O)N1C(=O)N(CCOC)C=C1C1=CC=CC=C1 HCKXIENNWYVMBG-UHFFFAOYSA-N 0.000 description 1
- IHAYBLBOZGDCME-UHFFFAOYSA-N 1-(2-methoxyethyl)-3-(2-methylbenzoyl)-4-phenylimidazolidin-2-one Chemical compound O=C1N(CCOC)CC(C=2C=CC=CC=2)N1C(=O)C1=CC=CC=C1C IHAYBLBOZGDCME-UHFFFAOYSA-N 0.000 description 1
- LSPJMBLAOWKCPK-UHFFFAOYSA-N 1-(2-methoxyethyl)-4-(3-methylphenyl)imidazolidin-2-one Chemical compound N1C(=O)N(CCOC)CC1C1=CC=CC(C)=C1 LSPJMBLAOWKCPK-UHFFFAOYSA-N 0.000 description 1
- FJKVAMGLMXDBGJ-UHFFFAOYSA-N 1-(2-methoxyethyl)-4-[4-(trifluoromethyl)phenyl]imidazolidin-2-one Chemical compound N1C(=O)N(CCOC)CC1C1=CC=C(C(F)(F)F)C=C1 FJKVAMGLMXDBGJ-UHFFFAOYSA-N 0.000 description 1
- LDXJRKWFNNFDSA-UHFFFAOYSA-N 2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound C1CN(CC2=NNN=C21)CC(=O)N3CCN(CC3)C4=CN=C(N=C4)NCC5=CC(=CC=C5)OC(F)(F)F LDXJRKWFNNFDSA-UHFFFAOYSA-N 0.000 description 1
- MZNKYQYJLAEUCZ-UHFFFAOYSA-N 2-(2-oxo-4-phenylimidazolidin-1-yl)ethyl 4-methylbenzoate Chemical compound C1=CC(C)=CC=C1C(=O)OCCN1C(=O)NC(C=2C=CC=CC=2)C1 MZNKYQYJLAEUCZ-UHFFFAOYSA-N 0.000 description 1
- YSRXTEPZMFRFCO-UHFFFAOYSA-N 2-(2-oxo-5-phenyl-1h-imidazol-3-yl)ethyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCCN(C(N1)=O)C=C1C1=CC=CC=C1 YSRXTEPZMFRFCO-UHFFFAOYSA-N 0.000 description 1
- GUJVSACUUYJUNG-UHFFFAOYSA-N 2-(5-phenyl-1,2-dihydroimidazol-3-yl)ethyl 4-(trifluoromethyl)benzoate Chemical compound C1=CC(C(F)(F)F)=CC=C1C(=O)OCCN1C=C(C=2C=CC=CC=2)NC1 GUJVSACUUYJUNG-UHFFFAOYSA-N 0.000 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- WZWWEVCLPKAQTA-UHFFFAOYSA-N 2-bromo-1-(2-chlorophenyl)ethanone Chemical compound ClC1=CC=CC=C1C(=O)CBr WZWWEVCLPKAQTA-UHFFFAOYSA-N 0.000 description 1
- BFBKUYFMLNOLOQ-UHFFFAOYSA-N 2-butoxyethanamine Chemical compound CCCCOCCN BFBKUYFMLNOLOQ-UHFFFAOYSA-N 0.000 description 1
- GUXJXWKCUUWCLX-UHFFFAOYSA-N 2-methyl-2-oxazoline Chemical compound CC1=NCCO1 GUXJXWKCUUWCLX-UHFFFAOYSA-N 0.000 description 1
- ZXTHWIZHGLNEPG-UHFFFAOYSA-N 2-phenyl-4,5-dihydro-1,3-oxazole Chemical compound O1CCN=C1C1=CC=CC=C1 ZXTHWIZHGLNEPG-UHFFFAOYSA-N 0.000 description 1
- DQGFAMWKZFDSKW-UHFFFAOYSA-N 3-(2,4-dichlorobenzoyl)-1-(2-methoxyethyl)-4-phenylimidazol-2-one Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(=O)N1C(=O)N(CCOC)C=C1C1=CC=CC=C1 DQGFAMWKZFDSKW-UHFFFAOYSA-N 0.000 description 1
- YJDRVSJGZCFZTQ-UHFFFAOYSA-N 3-(2-chlorobenzoyl)-1-(2-methoxyethyl)-4-phenylimidazolidin-2-one Chemical compound O=C1N(CCOC)CC(C=2C=CC=CC=2)N1C(=O)C1=CC=CC=C1Cl YJDRVSJGZCFZTQ-UHFFFAOYSA-N 0.000 description 1
- ADTDHVCWTLTZMW-UHFFFAOYSA-N 3-(2-hydroxyethyl)-5-phenyl-1h-imidazole-2-thione Chemical compound N1C(=S)N(CCO)C=C1C1=CC=CC=C1 ADTDHVCWTLTZMW-UHFFFAOYSA-N 0.000 description 1
- AMJOCQNFFKVXHL-UHFFFAOYSA-N 3-(2-methoxybenzoyl)-1-(2-methoxyethyl)-4-phenylimidazolidin-2-one Chemical compound O=C1N(CCOC)CC(C=2C=CC=CC=2)N1C(=O)C1=CC=CC=C1OC AMJOCQNFFKVXHL-UHFFFAOYSA-N 0.000 description 1
- KFEAAJBPOBCQCP-UHFFFAOYSA-N 3-ethenyl-5-phenyl-1h-imidazole-2-thione Chemical compound N1C(=S)N(C=C)C=C1C1=CC=CC=C1 KFEAAJBPOBCQCP-UHFFFAOYSA-N 0.000 description 1
- OLYKFGWSRLGXGS-UHFFFAOYSA-N 5-(2-chlorophenyl)-3-(2-methoxyethyl)-1h-imidazol-2-one Chemical compound N1C(=O)N(CCOC)C=C1C1=CC=CC=C1Cl OLYKFGWSRLGXGS-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 229940124339 anthelmintic agent Drugs 0.000 description 1
- 239000000921 anthelmintic agent Substances 0.000 description 1
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 239000002815 homogeneous catalyst Substances 0.000 description 1
- 238000009905 homogeneous catalytic hydrogenation reaction Methods 0.000 description 1
- 238000006197 hydroboration reaction Methods 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 150000003385 sodium Chemical class 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- ZVCDLGYNFYZZOK-UHFFFAOYSA-M sodium cyanate Chemical compound [Na]OC#N ZVCDLGYNFYZZOK-UHFFFAOYSA-M 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 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
- C07D233/66—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
- C07D233/70—One oxygen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D233/30—Oxygen or sulfur atoms
- C07D233/32—One oxygen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D233/30—Oxygen or sulfur atoms
- C07D233/32—One oxygen atom
- C07D233/38—One oxygen atom with acyl radicals or hetero atoms directly attached to ring nitrogen 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
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D233/30—Oxygen or sulfur atoms
- C07D233/42—Sulfur atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US68031176A | 1976-04-26 | 1976-04-26 | |
| US05/739,924 US4090025A (en) | 1976-04-26 | 1976-11-08 | Intermediates for synthesis of tetramisole, levamisole and their derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO771422L true NO771422L (no) | 1977-10-27 |
Family
ID=27102431
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO771422A NO771422L (no) | 1976-04-26 | 1977-04-25 | Fremgangsm}te for fremstilling av tetramisol, levamisol og derivater derav |
Country Status (14)
| Country | Link |
|---|---|
| JP (1) | JPS52142067A (fr) |
| AU (1) | AU2341277A (fr) |
| DD (1) | DD131175A5 (fr) |
| DE (1) | DE2718059A1 (fr) |
| DK (1) | DK181177A (fr) |
| ES (1) | ES458164A1 (fr) |
| FR (1) | FR2370735A1 (fr) |
| GB (2) | GB1579861A (fr) |
| IL (1) | IL51654A0 (fr) |
| IT (1) | IT1086883B (fr) |
| NL (1) | NL7704424A (fr) |
| NO (1) | NO771422L (fr) |
| NZ (1) | NZ183622A (fr) |
| SE (1) | SE7704745L (fr) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL51639A0 (en) * | 1976-04-26 | 1977-05-31 | American Cyanamid Co | New synthesis of tetramisole levamisole and their derivatives |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3726894A (en) * | 1971-06-24 | 1973-04-10 | American Cyanamid Co | The compound 1-(2-hydroxyethyl)-4-phenyl-2-imidazolidinethione |
| GB1435900A (en) * | 1972-10-04 | 1976-05-19 | Agfa Gevaert | Method for the preparation of planographic printing plates |
| FR2258379A1 (en) * | 1974-01-21 | 1975-08-18 | Aries Robert | Imidazo thiazolidine anthelmintics - prepd from an ethylene thiourea and a haloethanol, halogenation and cyclisation |
-
1977
- 1977-03-14 IL IL51654A patent/IL51654A0/xx unknown
- 1977-03-16 NZ NZ183622A patent/NZ183622A/xx unknown
- 1977-03-17 GB GB11485/77A patent/GB1579861A/en not_active Expired
- 1977-03-17 GB GB3668/79A patent/GB1579862A/en not_active Expired
- 1977-03-18 AU AU23412/77A patent/AU2341277A/en not_active Expired
- 1977-04-07 IT IT48871/77A patent/IT1086883B/it active
- 1977-04-22 DE DE19772718059 patent/DE2718059A1/de not_active Withdrawn
- 1977-04-22 NL NL7704424A patent/NL7704424A/xx not_active Application Discontinuation
- 1977-04-25 NO NO771422A patent/NO771422L/no unknown
- 1977-04-25 DK DK181177A patent/DK181177A/da not_active Application Discontinuation
- 1977-04-25 SE SE7704745A patent/SE7704745L/xx unknown
- 1977-04-26 FR FR7712567A patent/FR2370735A1/fr not_active Withdrawn
- 1977-04-26 JP JP4745477A patent/JPS52142067A/ja active Pending
- 1977-04-26 ES ES458164A patent/ES458164A1/es not_active Expired
- 1977-04-26 DD DD7700198605A patent/DD131175A5/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES458164A1 (es) | 1978-08-16 |
| DD131175A5 (de) | 1978-06-07 |
| FR2370735A1 (fr) | 1978-06-09 |
| IT1086883B (it) | 1985-05-31 |
| IL51654A0 (en) | 1977-05-31 |
| JPS52142067A (en) | 1977-11-26 |
| GB1579861A (en) | 1980-11-26 |
| AU2341277A (en) | 1978-09-21 |
| DE2718059A1 (de) | 1977-11-10 |
| SE7704745L (sv) | 1977-10-27 |
| NZ183622A (en) | 1980-04-28 |
| GB1579862A (en) | 1980-11-26 |
| DK181177A (da) | 1977-10-27 |
| NL7704424A (nl) | 1977-10-28 |
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