BE531460A - - Google Patents
Info
- Publication number
- BE531460A BE531460A BE531460DA BE531460A BE 531460 A BE531460 A BE 531460A BE 531460D A BE531460D A BE 531460DA BE 531460 A BE531460 A BE 531460A
- Authority
- BE
- Belgium
- Prior art keywords
- group
- preparation according
- bis
- crystallized
- melts
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 33
- 238000002360 preparation method Methods 0.000 claims description 16
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
- 239000011780 sodium chloride Substances 0.000 claims description 9
- 238000006460 hydrolysis reaction Methods 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 150000003512 tertiary amines Chemical class 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims description 6
- 238000006722 reduction reaction Methods 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 125000002252 acyl group Chemical group 0.000 claims description 5
- 125000004432 carbon atoms Chemical group C* 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000001302 tertiary amino group Chemical group 0.000 claims description 4
- 238000007792 addition Methods 0.000 claims description 3
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 125000000018 nitroso group Chemical group N(=O)* 0.000 claims description 3
- 238000000197 pyrolysis Methods 0.000 claims description 3
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
- 230000001476 alcoholic Effects 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 230000001681 protective Effects 0.000 claims 3
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims 2
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
- 239000012458 free base Substances 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 1
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 125000001453 quaternary ammonium group Chemical group 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 65
- 239000000155 melt Substances 0.000 description 56
- -1 amine salt Chemical class 0.000 description 43
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 40
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 34
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 21
- 238000002844 melting Methods 0.000 description 20
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 18
- 239000000243 solution Substances 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 10
- 238000010992 reflux Methods 0.000 description 10
- 239000000203 mixture Substances 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N iso-propanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 230000005712 crystallization Effects 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-Ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 238000002425 crystallisation Methods 0.000 description 5
- 238000000354 decomposition reaction Methods 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 229960000583 Acetic Acid Drugs 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 230000000875 corresponding Effects 0.000 description 4
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- DZGCGKFAPXFTNM-UHFFFAOYSA-N ethanol;hydron;chloride Chemical compound Cl.CCO DZGCGKFAPXFTNM-UHFFFAOYSA-N 0.000 description 3
- 239000008079 hexane Substances 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- OCZDCIYGECBNKL-UHFFFAOYSA-N lithium;alumanuide Chemical compound [Li+].[AlH4-] OCZDCIYGECBNKL-UHFFFAOYSA-N 0.000 description 3
- 150000003141 primary amines Chemical class 0.000 description 3
- 125000006239 protecting group Chemical group 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 230000002829 reduced Effects 0.000 description 3
- 238000005932 reductive alkylation reaction Methods 0.000 description 3
- 150000003335 secondary amines Chemical class 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 2
- CNHDIAIOKMXOLK-UHFFFAOYSA-N 2-methylbenzene-1,4-diol Chemical compound CC1=CC(O)=CC=C1O CNHDIAIOKMXOLK-UHFFFAOYSA-N 0.000 description 2
- JKRIFKGKSXBJND-UHFFFAOYSA-N 3-methoxy-4-octoxyaniline Chemical compound CCCCCCCCOC1=CC=C(N)C=C1OC JKRIFKGKSXBJND-UHFFFAOYSA-N 0.000 description 2
- JVWJLCVWFDMNCA-UHFFFAOYSA-N 4-butoxy-3-methylaniline Chemical compound CCCCOC1=CC=C(N)C=C1C JVWJLCVWFDMNCA-UHFFFAOYSA-N 0.000 description 2
- BLQFHJKRTDIZLX-UHFFFAOYSA-N 5-amino-2-methoxyphenol Chemical compound COC1=CC=C(N)C=C1O BLQFHJKRTDIZLX-UHFFFAOYSA-N 0.000 description 2
- WKASANADPAHSMQ-UHFFFAOYSA-N C(C)NC1=CC(=C(OCCCCCC)C=C1)C Chemical compound C(C)NC1=CC(=C(OCCCCCC)C=C1)C WKASANADPAHSMQ-UHFFFAOYSA-N 0.000 description 2
- KRVKLECAMISQEC-UHFFFAOYSA-N CC1=C(OCCC)C=CC(=C1)N(C)C Chemical compound CC1=C(OCCC)C=CC(=C1)N(C)C KRVKLECAMISQEC-UHFFFAOYSA-N 0.000 description 2
- CZHSISCYCBTLGU-UHFFFAOYSA-N COC1=C(OCCCC)C=CC(=C1)N(C)C Chemical compound COC1=C(OCCCC)C=CC(=C1)N(C)C CZHSISCYCBTLGU-UHFFFAOYSA-N 0.000 description 2
- GVDBASJANMHKDJ-UHFFFAOYSA-N COC1=C(OCCCCCC)C=CC(=C1)N(C)C Chemical compound COC1=C(OCCCCCC)C=CC(=C1)N(C)C GVDBASJANMHKDJ-UHFFFAOYSA-N 0.000 description 2
- PKBCHQUOKHEDOJ-UHFFFAOYSA-N COC1=C(OCCCCCCC)C=CC(=C1)N(C)C Chemical compound COC1=C(OCCCCCCC)C=CC(=C1)N(C)C PKBCHQUOKHEDOJ-UHFFFAOYSA-N 0.000 description 2
- AVIDZQVUWISHES-UHFFFAOYSA-N N-(4-hydroxy-3-methylphenyl)acetamide Chemical compound CC(=O)NC1=CC=C(O)C(C)=C1 AVIDZQVUWISHES-UHFFFAOYSA-N 0.000 description 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M Potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- 241000242680 Schistosoma mansoni Species 0.000 description 2
- NDVLTYZPCACLMA-UHFFFAOYSA-N Silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M Sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxyl anion Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- HPQVWDOOUQVBTO-UHFFFAOYSA-N lithium aluminium hydride Substances [Li+].[Al-] HPQVWDOOUQVBTO-UHFFFAOYSA-N 0.000 description 2
- WDWDWGRYHDPSDS-UHFFFAOYSA-N methanimine Chemical compound N=C WDWDWGRYHDPSDS-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 238000006053 organic reaction Methods 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000012265 solid product Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- QDXORTKZTNOXOP-UHFFFAOYSA-N 2-amino-6-methoxyphenol Chemical compound COC1=CC=CC(N)=C1O QDXORTKZTNOXOP-UHFFFAOYSA-N 0.000 description 1
- PMTVEXBJLIRTEJ-UHFFFAOYSA-N 2-methyl-4-nitrosophenol Chemical compound CC1=CC(N=O)=CC=C1O PMTVEXBJLIRTEJ-UHFFFAOYSA-N 0.000 description 1
- REKLNYYDMMZVEZ-UHFFFAOYSA-N 3-methoxy-N,N-dimethyl-4-octoxyaniline Chemical compound CCCCCCCCOC1=CC=C(N(C)C)C=C1OC REKLNYYDMMZVEZ-UHFFFAOYSA-N 0.000 description 1
- LJIKASITLSOBIY-UHFFFAOYSA-N 3-methoxy-N,N-dimethyl-4-propoxyaniline Chemical compound CCCOC1=CC=C(N(C)C)C=C1OC LJIKASITLSOBIY-UHFFFAOYSA-N 0.000 description 1
- BODIKTRHOMTUCO-UHFFFAOYSA-N 3-methyl-4-(methylamino)phenol Chemical compound CNC1=CC=C(O)C=C1C BODIKTRHOMTUCO-UHFFFAOYSA-N 0.000 description 1
- SEHGINBIAYLEJD-UHFFFAOYSA-N 3-methyl-4-octoxyaniline Chemical compound CCCCCCCCOC1=CC=C(N)C=C1C SEHGINBIAYLEJD-UHFFFAOYSA-N 0.000 description 1
- NURKNCXNNBJSSZ-UHFFFAOYSA-N 4-(ethylamino)-2-methylphenol Chemical compound CCNC1=CC=C(O)C(C)=C1 NURKNCXNNBJSSZ-UHFFFAOYSA-N 0.000 description 1
- XTBGKGYKNKIIJI-UHFFFAOYSA-N 4-heptoxy-3-methoxyaniline Chemical compound CCCCCCCOC1=CC=C(N)C=C1OC XTBGKGYKNKIIJI-UHFFFAOYSA-N 0.000 description 1
- DPSVOMOEWBLGJI-UHFFFAOYSA-N 4-hexoxy-3-methylaniline Chemical compound CCCCCCOC1=CC=C(N)C=C1C DPSVOMOEWBLGJI-UHFFFAOYSA-N 0.000 description 1
- LMENRXCWBNYKDI-UHFFFAOYSA-N C(C)(=O)NC1=CC(=C(C=C1)OCCC)OC Chemical compound C(C)(=O)NC1=CC(=C(C=C1)OCCC)OC LMENRXCWBNYKDI-UHFFFAOYSA-N 0.000 description 1
- AMBSTTIBHBKURC-UHFFFAOYSA-N C(C)(=O)NC1=CC(=C(OCCC)C=C1)C Chemical compound C(C)(=O)NC1=CC(=C(OCCC)C=C1)C AMBSTTIBHBKURC-UHFFFAOYSA-N 0.000 description 1
- KEWNJBZXFYYGJZ-UHFFFAOYSA-N C(C)(=O)NC1=CC(=C(OCCCC)C=C1)C Chemical compound C(C)(=O)NC1=CC(=C(OCCCC)C=C1)C KEWNJBZXFYYGJZ-UHFFFAOYSA-N 0.000 description 1
- XYXJGHIEGCMTJH-UHFFFAOYSA-N C(C)(=O)NC1=CC(=C(OCCCC)C=C1)OC Chemical compound C(C)(=O)NC1=CC(=C(OCCCC)C=C1)OC XYXJGHIEGCMTJH-UHFFFAOYSA-N 0.000 description 1
- UIOGYPSOVGYFGC-UHFFFAOYSA-N C(C)(=O)NC1=CC(=C(OCCCCC)C=C1)C Chemical compound C(C)(=O)NC1=CC(=C(OCCCCC)C=C1)C UIOGYPSOVGYFGC-UHFFFAOYSA-N 0.000 description 1
- GYDMRUXZHADMTI-UHFFFAOYSA-N C(C)(=O)NC1=CC(=C(OCCCCCCC)C=C1)C Chemical compound C(C)(=O)NC1=CC(=C(OCCCCCCC)C=C1)C GYDMRUXZHADMTI-UHFFFAOYSA-N 0.000 description 1
- QYFUJHZGQOWSFE-UHFFFAOYSA-N C(C)(=O)NC1=CC(=C(OCCCCCCC)C=C1)OC Chemical compound C(C)(=O)NC1=CC(=C(OCCCCCCC)C=C1)OC QYFUJHZGQOWSFE-UHFFFAOYSA-N 0.000 description 1
- PGXOXZQDNJGRNR-UHFFFAOYSA-N C(C)(=O)NC1=CC(=C(OCCCCCCCC)C=C1)C Chemical compound C(C)(=O)NC1=CC(=C(OCCCCCCCC)C=C1)C PGXOXZQDNJGRNR-UHFFFAOYSA-N 0.000 description 1
- WCZOJEXFQSDDDU-UHFFFAOYSA-N C(C)(=O)NC1=CC(=C(OCCCCCCCC)C=C1)OC Chemical compound C(C)(=O)NC1=CC(=C(OCCCCCCCC)C=C1)OC WCZOJEXFQSDDDU-UHFFFAOYSA-N 0.000 description 1
- DXHMJLJCKZNHPX-UHFFFAOYSA-N C(C)(=O)NC1=CC(=C(OCCCCCCCCC)C=C1)C Chemical compound C(C)(=O)NC1=CC(=C(OCCCCCCCCC)C=C1)C DXHMJLJCKZNHPX-UHFFFAOYSA-N 0.000 description 1
- DJISHQDYFONWTF-UHFFFAOYSA-N C(C)NC1=CC(=C(OCCCCC)C=C1)C Chemical compound C(C)NC1=CC(=C(OCCCCC)C=C1)C DJISHQDYFONWTF-UHFFFAOYSA-N 0.000 description 1
- BCYZSGDGCWMNDL-UHFFFAOYSA-N CC1=C(OCCCC)C=CC(=C1)N(C)C Chemical compound CC1=C(OCCCC)C=CC(=C1)N(C)C BCYZSGDGCWMNDL-UHFFFAOYSA-N 0.000 description 1
- VJUBDKBVAOHNHS-UHFFFAOYSA-N CC1=C(OCCCCC)C=CC(=C1)N(C)C Chemical compound CC1=C(OCCCCC)C=CC(=C1)N(C)C VJUBDKBVAOHNHS-UHFFFAOYSA-N 0.000 description 1
- HPFQVVNHFVAMPR-UHFFFAOYSA-N CC1=C(OCCCCC)C=CC(=C1)NC Chemical compound CC1=C(OCCCCC)C=CC(=C1)NC HPFQVVNHFVAMPR-UHFFFAOYSA-N 0.000 description 1
- YSIAIEIPQMADBD-UHFFFAOYSA-N CC1=C(OCCCCCC)C=CC(=C1)N(C)C Chemical compound CC1=C(OCCCCCC)C=CC(=C1)N(C)C YSIAIEIPQMADBD-UHFFFAOYSA-N 0.000 description 1
- LQQLNCUDGFWTFC-UHFFFAOYSA-N CC1=C(OCCCCCCC)C=CC(=C1)NC Chemical compound CC1=C(OCCCCCCC)C=CC(=C1)NC LQQLNCUDGFWTFC-UHFFFAOYSA-N 0.000 description 1
- PKZJMONAMJMCOI-UHFFFAOYSA-N CC1=C(OCCCCCCCC)C=CC(=C1)N(C)C Chemical compound CC1=C(OCCCCCCCC)C=CC(=C1)N(C)C PKZJMONAMJMCOI-UHFFFAOYSA-N 0.000 description 1
- LNKSPTLUZKGQIB-UHFFFAOYSA-N CC1=C(OCCCCCCCCC)C=CC(=C1)N(C)C Chemical compound CC1=C(OCCCCCCCCC)C=CC(=C1)N(C)C LNKSPTLUZKGQIB-UHFFFAOYSA-N 0.000 description 1
- FYLBCLHVURVWSL-UHFFFAOYSA-N CC1=C(OCCCCCCCCC)C=CC(=C1)NC Chemical compound CC1=C(OCCCCCCCCC)C=CC(=C1)NC FYLBCLHVURVWSL-UHFFFAOYSA-N 0.000 description 1
- 238000006969 Curtius rearrangement reaction Methods 0.000 description 1
- 238000006105 Hofmann reaction Methods 0.000 description 1
- 210000004185 Liver Anatomy 0.000 description 1
- 210000001758 Mesenteric Veins Anatomy 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N Methyl iodide Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- HQSBKFBRKYNLCZ-UHFFFAOYSA-N N-(3-hydroxy-4-methoxyphenyl)acetamide Chemical compound COC1=CC=C(NC(C)=O)C=C1O HQSBKFBRKYNLCZ-UHFFFAOYSA-N 0.000 description 1
- KIZWIAQUWRXFNC-UHFFFAOYSA-N N-(4-hydroxy-3-methoxyphenyl)acetamide Chemical compound COC1=CC(NC(C)=O)=CC=C1O KIZWIAQUWRXFNC-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N Octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 206010057249 Phagocytosis Diseases 0.000 description 1
- 210000003240 Portal Vein Anatomy 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- YNWPCUJLQAYKGD-UHFFFAOYSA-N S(=O)(=O)(O)OC1=C(C=C(C=C1)NC)C Chemical compound S(=O)(=O)(O)OC1=C(C=C(C=C1)NC)C YNWPCUJLQAYKGD-UHFFFAOYSA-N 0.000 description 1
- WXLBMCSBQIOBKT-UHFFFAOYSA-N S(=O)(=O)(O)OC1=C(C=C(C=C1)NCC)C Chemical compound S(=O)(=O)(O)OC1=C(C=C(C=C1)NCC)C WXLBMCSBQIOBKT-UHFFFAOYSA-N 0.000 description 1
- PGNZIEKVQCKOBT-UHFFFAOYSA-N Tetraazidomethane Chemical compound [N-]=[N+]=NC(N=[N+]=[N-])(N=[N+]=[N-])N=[N+]=[N-] PGNZIEKVQCKOBT-UHFFFAOYSA-N 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N [N-]=C=O Chemical compound [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 125000004429 atoms Chemical group 0.000 description 1
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000001743 benzylic group Chemical group 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 125000004181 carboxyalkyl group Chemical group 0.000 description 1
- 230000003197 catalytic Effects 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000006264 debenzylation reaction Methods 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- QSJXEFYPDANLFS-UHFFFAOYSA-N diacetyl Chemical group CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 201000009910 diseases by infectious agent Diseases 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- QUSNBJAOOMFDIB-UHFFFAOYSA-N ethyl amine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- FFLYUXVZEPLMCL-UHFFFAOYSA-N ethylchloranuidyl formate Chemical compound CC[Cl-]OC=O FFLYUXVZEPLMCL-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- TWRQCVNFACGORI-UHFFFAOYSA-N hexane;dihydrochloride Chemical compound Cl.Cl.CCCCCC TWRQCVNFACGORI-UHFFFAOYSA-N 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- IMNFDUFMRHMDMM-UHFFFAOYSA-N n-heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L na2so4 Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
- 238000007034 nitrosation reaction Methods 0.000 description 1
- 150000002832 nitroso derivatives Chemical class 0.000 description 1
- ABOWRJQOEJPPFS-UHFFFAOYSA-N nonane;dihydrochloride Chemical compound Cl.Cl.CCCCCCCCC ABOWRJQOEJPPFS-UHFFFAOYSA-N 0.000 description 1
- 230000003000 nontoxic Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 230000008782 phagocytosis Effects 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000001376 precipitating Effects 0.000 description 1
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- KGMXPXPXPAAUMD-UHFFFAOYSA-N propane;dihydrochloride Chemical compound Cl.Cl.CCC KGMXPXPXPAAUMD-UHFFFAOYSA-N 0.000 description 1
- 229910001923 silver oxide Inorganic materials 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- 229940013123 stannous chloride Drugs 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000001225 therapeutic Effects 0.000 description 1
- FWPIDFUJEMBDLS-UHFFFAOYSA-L tin dichloride dihydrate Chemical compound O.O.Cl[Sn]Cl FWPIDFUJEMBDLS-UHFFFAOYSA-L 0.000 description 1
- 230000001131 transforming Effects 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE531460A true BE531460A (de) |
Family
ID=163790
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE531460D BE531460A (de) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE531460A (de) |
-
0
- BE BE531460D patent/BE531460A/fr unknown
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