PL59726B1 - - Google Patents
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- Publication number
- PL59726B1 PL59726B1 PL114350A PL11435066A PL59726B1 PL 59726 B1 PL59726 B1 PL 59726B1 PL 114350 A PL114350 A PL 114350A PL 11435066 A PL11435066 A PL 11435066A PL 59726 B1 PL59726 B1 PL 59726B1
- Authority
- PL
- Poland
- Prior art keywords
- dibenzo
- methyl
- piperidyl
- chloro
- model
- Prior art date
Links
- -1 allkenyl Chemical group 0.000 claims description 61
- GWYPDXLJACEENP-UHFFFAOYSA-N 1,3-cycloheptadiene Chemical compound C1CC=CC=CC1 GWYPDXLJACEENP-UHFFFAOYSA-N 0.000 claims description 40
- 150000001875 compounds Chemical class 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical group O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- CHVJITGCYZJHLR-UHFFFAOYSA-N cyclohepta-1,3,5-triene Chemical class C1C=CC=CC=C1 CHVJITGCYZJHLR-UHFFFAOYSA-N 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 6
- 125000000217 alkyl group Chemical group 0.000 claims 5
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- 125000003342 alkenyl group Chemical group 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims 2
- 125000000304 alkynyl group Chemical group 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 230000018044 dehydration Effects 0.000 claims 2
- 238000006297 dehydration reaction Methods 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 125000003884 phenylalkyl group Chemical group 0.000 claims 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims 1
- 125000004414 alkyl thio group Chemical group 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 238000010586 diagram Methods 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- LJZPPWWHKPGCHS-UHFFFAOYSA-N propargyl chloride Chemical compound ClCC#C LJZPPWWHKPGCHS-UHFFFAOYSA-N 0.000 claims 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 239000002023 wood Substances 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 35
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 33
- 238000002844 melting Methods 0.000 description 29
- 230000008018 melting Effects 0.000 description 29
- 239000000243 solution Substances 0.000 description 25
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 14
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- 239000012153 distilled water Substances 0.000 description 11
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 10
- 238000009835 boiling Methods 0.000 description 9
- BSDGZUDFPKIYQG-UHFFFAOYSA-N 4-bromopyridine Chemical compound BrC1=CC=NC=C1 BSDGZUDFPKIYQG-UHFFFAOYSA-N 0.000 description 7
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 7
- WVDDGKGOMKODPV-UHFFFAOYSA-N benzyl alcohol Substances OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 7
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- 229940102396 methyl bromide Drugs 0.000 description 7
- 229910052697 platinum Inorganic materials 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 229920000137 polyphosphoric acid Polymers 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 229910052744 lithium Inorganic materials 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- ORILYTVJVMAKLC-UHFFFAOYSA-N Adamantane Natural products C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 125000005605 benzo group Chemical group 0.000 description 3
- 235000019445 benzyl alcohol Nutrition 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- RXFFMEZSLOLKKZ-UHFFFAOYSA-N 2-[(2-chlorophenyl)methyl]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1CC1=CC=CC=C1Cl RXFFMEZSLOLKKZ-UHFFFAOYSA-N 0.000 description 2
- WEGDCUCAHSQZOU-UHFFFAOYSA-N 2-[2-[(2-chlorophenyl)methyl]phenyl]acetonitrile Chemical compound ClC1=C(CC2=C(C=CC=C2)CC#N)C=CC=C1 WEGDCUCAHSQZOU-UHFFFAOYSA-N 0.000 description 2
- WNZQDUSMALZDQF-UHFFFAOYSA-N 2-benzofuran-1(3H)-one Chemical compound C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- IMRCWTBBTYVQHZ-UHFFFAOYSA-N lithium;4h-pyridin-4-ide Chemical compound [Li+].C1=CN=CC=[C-]1 IMRCWTBBTYVQHZ-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- ANRQGKOBLBYXFM-UHFFFAOYSA-M phenylmagnesium bromide Chemical compound Br[Mg]C1=CC=CC=C1 ANRQGKOBLBYXFM-UHFFFAOYSA-M 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- DXYWZSWCAGJDPP-UHFFFAOYSA-N 1-(bromomethyl)-2-[(2-chlorophenyl)methyl]benzene Chemical compound ClC1=C(CC2=C(CBr)C=CC=C2)C=CC=C1 DXYWZSWCAGJDPP-UHFFFAOYSA-N 0.000 description 1
- CWDWXRDUALJDAJ-UHFFFAOYSA-N 1-(bromomethyl)-2-[(3-chlorophenyl)methyl]benzene Chemical compound ClC=1C=C(CC2=C(CBr)C=CC=C2)C=CC1 CWDWXRDUALJDAJ-UHFFFAOYSA-N 0.000 description 1
- NOZUVSYXSQUKOH-UHFFFAOYSA-N 1-benzyl-2-(bromomethyl)-3-chlorobenzene Chemical compound C(C1=CC=CC=C1)C1=C(CBr)C(=CC=C1)Cl NOZUVSYXSQUKOH-UHFFFAOYSA-N 0.000 description 1
- BDQXFTPBZBXGEV-UHFFFAOYSA-N 1-benzyl-2-(bromomethyl)-4-chlorobenzene Chemical compound C(C1=CC=CC=C1)C1=C(CBr)C=C(C=C1)Cl BDQXFTPBZBXGEV-UHFFFAOYSA-N 0.000 description 1
- ZXRINEZYHRXKAH-UHFFFAOYSA-N 2-(2-benzyl-3-chlorophenyl)acetic acid Chemical compound C(C1=CC=CC=C1)C1=C(C=CC=C1Cl)CC(=O)O ZXRINEZYHRXKAH-UHFFFAOYSA-N 0.000 description 1
- SVGUXQVCPOJGAR-UHFFFAOYSA-N 2-(2-benzyl-3-chlorophenyl)acetonitrile Chemical compound C(C1=CC=CC=C1)C1=C(C=CC=C1Cl)CC#N SVGUXQVCPOJGAR-UHFFFAOYSA-N 0.000 description 1
- JMVXAHRELATLSY-UHFFFAOYSA-N 2-(2-benzyl-4-chlorophenyl)acetic acid Chemical compound C(C1=CC=CC=C1)C1=C(C=CC(=C1)Cl)CC(=O)O JMVXAHRELATLSY-UHFFFAOYSA-N 0.000 description 1
- BYTYJGSNBJMICO-UHFFFAOYSA-N 2-(2-benzyl-4-chlorophenyl)acetonitrile Chemical compound C(C1=CC=CC=C1)C1=C(C=CC(=C1)Cl)CC#N BYTYJGSNBJMICO-UHFFFAOYSA-N 0.000 description 1
- IYTIEAOSCNDYCY-UHFFFAOYSA-N 2-(2-benzyl-5-chlorophenyl)acetic acid Chemical compound C(C1=CC=CC=C1)C1=C(C=C(C=C1)Cl)CC(=O)O IYTIEAOSCNDYCY-UHFFFAOYSA-N 0.000 description 1
- YSRATGCOXIFBSF-UHFFFAOYSA-N 2-(2-benzyl-5-chlorophenyl)acetonitrile Chemical compound C(C1=CC=CC=C1)C1=C(C=C(C=C1)Cl)CC#N YSRATGCOXIFBSF-UHFFFAOYSA-N 0.000 description 1
- BCIXTEPSRAKKLB-UHFFFAOYSA-N 2-(2-benzyl-6-chlorophenyl)acetic acid Chemical compound C(C1=CC=CC=C1)C1=C(C(=CC=C1)Cl)CC(=O)O BCIXTEPSRAKKLB-UHFFFAOYSA-N 0.000 description 1
- CZIABFNTNFAAGB-UHFFFAOYSA-N 2-(2-benzyl-6-chlorophenyl)acetonitrile Chemical compound C(C1=CC=CC=C1)C1=C(C(=CC=C1)Cl)CC#N CZIABFNTNFAAGB-UHFFFAOYSA-N 0.000 description 1
- FSMXJLAATHSRCB-UHFFFAOYSA-N 2-(3-chlorobenzoyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)C1=CC=CC(Cl)=C1 FSMXJLAATHSRCB-UHFFFAOYSA-N 0.000 description 1
- LIWZNADQJPFBBR-UHFFFAOYSA-N 2-[(3-chlorophenyl)methyl]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1CC1=CC=CC(Cl)=C1 LIWZNADQJPFBBR-UHFFFAOYSA-N 0.000 description 1
- KANMVICUKRMNFU-UHFFFAOYSA-N 2-[2-[(2-chlorophenyl)methyl]phenyl]acetic acid Chemical compound OC(=O)CC1=CC=CC=C1CC1=CC=CC=C1Cl KANMVICUKRMNFU-UHFFFAOYSA-N 0.000 description 1
- FSDACKCGVUUVDI-UHFFFAOYSA-N 2-[2-[(2-chlorophenyl)methyl]phenyl]acetyl chloride Chemical compound ClC1=C(CC2=C(C=CC=C2)CC(=O)Cl)C=CC=C1 FSDACKCGVUUVDI-UHFFFAOYSA-N 0.000 description 1
- YMQPBGUSASPGPC-UHFFFAOYSA-N 2-[2-[(3-chlorophenyl)methyl]phenyl]acetic acid Chemical compound ClC=1C=C(CC2=C(C=CC=C2)CC(=O)O)C=CC1 YMQPBGUSASPGPC-UHFFFAOYSA-N 0.000 description 1
- NGIZGRYVQRJRST-UHFFFAOYSA-N 2-[2-[(4-methylphenyl)methyl]phenyl]acetic acid Chemical compound C1=CC(C)=CC=C1CC1=CC=CC=C1CC(O)=O NGIZGRYVQRJRST-UHFFFAOYSA-N 0.000 description 1
- HMAPQMIVZDDUHU-UHFFFAOYSA-N 2-[2-[(4-methylphenyl)methyl]phenyl]acetonitrile Chemical compound CC1=CC=C(CC2=C(C=CC=C2)CC#N)C=C1 HMAPQMIVZDDUHU-UHFFFAOYSA-N 0.000 description 1
- JEZQCHJJLYRNOZ-UHFFFAOYSA-N 2-benzoyl-3-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC(Cl)=C1C(=O)C1=CC=CC=C1 JEZQCHJJLYRNOZ-UHFFFAOYSA-N 0.000 description 1
- WEPCKTJPKYUIEC-UHFFFAOYSA-N 2-benzyl-1-(bromomethyl)-4-chlorobenzene Chemical compound C(C1=CC=CC=C1)C1=C(CBr)C=CC(=C1)Cl WEPCKTJPKYUIEC-UHFFFAOYSA-N 0.000 description 1
- BOZFADPBTXJVHH-UHFFFAOYSA-N 2-benzyl-3-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC(Cl)=C1CC1=CC=CC=C1 BOZFADPBTXJVHH-UHFFFAOYSA-N 0.000 description 1
- KGHIGKJJSTWDMM-UHFFFAOYSA-N 2-benzyl-4-chlorobenzoic acid Chemical compound OC(=O)C1=CC=C(Cl)C=C1CC1=CC=CC=C1 KGHIGKJJSTWDMM-UHFFFAOYSA-N 0.000 description 1
- VYSQGKSJOLXCME-UHFFFAOYSA-N 2-benzyl-5-chlorobenzoic acid Chemical compound C(C1=CC=CC=C1)C1=C(C(=O)O)C=C(C=C1)Cl VYSQGKSJOLXCME-UHFFFAOYSA-N 0.000 description 1
- MOOAHPLEXLVKBU-UHFFFAOYSA-N 2-benzyl-6-chlorobenzoic acid Chemical compound C(C1=CC=CC=C1)C1=C(C(=O)O)C(=CC=C1)Cl MOOAHPLEXLVKBU-UHFFFAOYSA-N 0.000 description 1
- URGQYBULFKLFMX-UHFFFAOYSA-N 2-chloro-6-formylbenzoic acid Chemical compound OC(=O)C1=C(Cl)C=CC=C1C=O URGQYBULFKLFMX-UHFFFAOYSA-N 0.000 description 1
- DYNFCHNNOHNJFG-UHFFFAOYSA-N 2-formylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C=O DYNFCHNNOHNJFG-UHFFFAOYSA-N 0.000 description 1
- BWUMCZISAYSMCC-UHFFFAOYSA-N 3-(2-chlorophenyl)-3H-2-benzofuran-1-one Chemical compound ClC1=CC=CC=C1C1C2=CC=CC=C2C(=O)O1 BWUMCZISAYSMCC-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- NGLYJLKDVODLLN-UHFFFAOYSA-N 3-bromo-7-chloro-3H-2-benzofuran-1-one Chemical compound BrC1OC(=O)C2=C(C=CC=C12)Cl NGLYJLKDVODLLN-UHFFFAOYSA-N 0.000 description 1
- 125000003852 3-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])* 0.000 description 1
- 125000006181 4-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])C([H])([H])* 0.000 description 1
- NQAMSLASTWZONN-UHFFFAOYSA-N 5-chloro-2-formylbenzoic acid Chemical compound OC(=O)C1=CC(Cl)=CC=C1C=O NQAMSLASTWZONN-UHFFFAOYSA-N 0.000 description 1
- FADOEOCVGLIMTN-UHFFFAOYSA-N 6-chloro-3-phenyl-3h-2-benzofuran-1-one Chemical compound O1C(=O)C2=CC(Cl)=CC=C2C1C1=CC=CC=C1 FADOEOCVGLIMTN-UHFFFAOYSA-N 0.000 description 1
- VWPZSNDYSLZHTO-UHFFFAOYSA-N 7-chloro-3-phenyl-3h-2-benzofuran-1-one Chemical compound O1C(=O)C=2C(Cl)=CC=CC=2C1C1=CC=CC=C1 VWPZSNDYSLZHTO-UHFFFAOYSA-N 0.000 description 1
- LLKCTHJTJUDDMG-UHFFFAOYSA-N 7-chloro-3h-2-benzofuran-1-one Chemical compound ClC1=CC=CC2=C1C(=O)OC2 LLKCTHJTJUDDMG-UHFFFAOYSA-N 0.000 description 1
- FDACASMXPXPOFS-UHFFFAOYSA-N C(C1=CC=CC=C1)C1=C(C(=O)OC)C(=CC=C1)Cl Chemical compound C(C1=CC=CC=C1)C1=C(C(=O)OC)C(=CC=C1)Cl FDACASMXPXPOFS-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241000662429 Fenerbahce Species 0.000 description 1
- PQBAWAQIRZIWIV-UHFFFAOYSA-N N-methylpyridinium Chemical compound C[N+]1=CC=CC=C1 PQBAWAQIRZIWIV-UHFFFAOYSA-N 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- BQRIIWKHNJGQFH-UHFFFAOYSA-M [Br-].[Mg+]C1=CC=CC=C1Cl Chemical compound [Br-].[Mg+]C1=CC=CC=C1Cl BQRIIWKHNJGQFH-UHFFFAOYSA-M 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- RMDOUGQKIZRFAY-UHFFFAOYSA-N methyl 2-[(2-chlorophenyl)methyl]benzoate Chemical compound ClC1=C(CC2=C(C(=O)OC)C=CC=C2)C=CC=C1 RMDOUGQKIZRFAY-UHFFFAOYSA-N 0.000 description 1
- PLMMKERRICOKPW-UHFFFAOYSA-N methyl 2-[(3-chlorophenyl)methyl]benzoate Chemical compound ClC=1C=C(CC2=C(C(=O)OC)C=CC=C2)C=CC1 PLMMKERRICOKPW-UHFFFAOYSA-N 0.000 description 1
- ZGTPQBKTLUFLAI-UHFFFAOYSA-N methyl 2-benzyl-4-chlorobenzoate Chemical compound C(C1=CC=CC=C1)C1=C(C(=O)OC)C=CC(=C1)Cl ZGTPQBKTLUFLAI-UHFFFAOYSA-N 0.000 description 1
- DRRKZMNTAFRCBS-UHFFFAOYSA-N methyl 2-benzyl-5-chlorobenzoate Chemical compound C(C1=CC=CC=C1)C1=C(C(=O)OC)C=C(C=C1)Cl DRRKZMNTAFRCBS-UHFFFAOYSA-N 0.000 description 1
- JAVRNIFMYIJXIE-UHFFFAOYSA-N methyl 2-chlorobenzoate Chemical compound COC(=O)C1=CC=CC=C1Cl JAVRNIFMYIJXIE-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 125000005936 piperidyl group Chemical group 0.000 description 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL59726B1 true PL59726B1 (cs) | 1970-02-26 |
Family
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