DE1620623A1 - Verfahren zur Herstellung von Dibenzodiazocinen - Google Patents
Verfahren zur Herstellung von DibenzodiazocinenInfo
- Publication number
- DE1620623A1 DE1620623A1 DE19661620623 DE1620623A DE1620623A1 DE 1620623 A1 DE1620623 A1 DE 1620623A1 DE 19661620623 DE19661620623 DE 19661620623 DE 1620623 A DE1620623 A DE 1620623A DE 1620623 A1 DE1620623 A1 DE 1620623A1
- Authority
- DE
- Germany
- Prior art keywords
- aminobenzophenone
- dibenzo
- bis
- acid
- heated
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 55
- 238000002360 preparation method Methods 0.000 title claims 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 claims description 39
- YZTFIKANQHTFDZ-UHFFFAOYSA-N diazocine Chemical class C1=CC=CN=NC=C1 YZTFIKANQHTFDZ-UHFFFAOYSA-N 0.000 claims description 26
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 23
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
- MAOBFOXLCJIFLV-UHFFFAOYSA-N (2-aminophenyl)-phenylmethanone Chemical compound NC1=CC=CC=C1C(=O)C1=CC=CC=C1 MAOBFOXLCJIFLV-UHFFFAOYSA-N 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 239000003377 acid catalyst Substances 0.000 claims description 5
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 4
- 125000004423 acyloxy group Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 235000019253 formic acid Nutrition 0.000 claims description 4
- 150000008064 anhydrides Chemical class 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 claims 1
- 241000272517 Anseriformes Species 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- -1 alkane carboxylic acid Chemical class 0.000 description 63
- 150000001875 compounds Chemical class 0.000 description 42
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 33
- 239000008096 xylene Substances 0.000 description 21
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 20
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 20
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- 239000000460 chlorine Substances 0.000 description 11
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 8
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 7
- 230000008018 melting Effects 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 150000002367 halogens Chemical class 0.000 description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002989 phenols Chemical class 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 241000271566 Aves Species 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- LSACYLWPPQLVSM-UHFFFAOYSA-N isobutyric acid anhydride Chemical compound CC(C)C(=O)OC(=O)C(C)C LSACYLWPPQLVSM-UHFFFAOYSA-N 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000012453 solvate Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- GFHWOKUXKUUKQJ-UHFFFAOYSA-N (2-amino-4-methoxyphenyl)-phenylmethanone Chemical compound NC1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1 GFHWOKUXKUUKQJ-UHFFFAOYSA-N 0.000 description 2
- LXJVUGANBDAASB-UHFFFAOYSA-N (2-amino-5-bromophenyl)-phenylmethanone Chemical compound NC1=CC=C(Br)C=C1C(=O)C1=CC=CC=C1 LXJVUGANBDAASB-UHFFFAOYSA-N 0.000 description 2
- GTGMXPIQRQSORU-UHFFFAOYSA-N (2-amino-5-chlorophenyl)-(2-fluorophenyl)methanone Chemical compound NC1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1F GTGMXPIQRQSORU-UHFFFAOYSA-N 0.000 description 2
- RIRNRSNOOZQYSI-UHFFFAOYSA-N (2-amino-5-chlorophenyl)-(3-fluorophenyl)methanone Chemical compound NC1=CC=C(Cl)C=C1C(=O)C1=CC=CC(F)=C1 RIRNRSNOOZQYSI-UHFFFAOYSA-N 0.000 description 2
- KCZMJDLXOIHHCO-UHFFFAOYSA-N (2-aminophenyl)-(3-chloro-4-methylphenyl)methanone Chemical compound NC1=C(C(=O)C2=CC(=C(C=C2)C)Cl)C=CC=C1 KCZMJDLXOIHHCO-UHFFFAOYSA-N 0.000 description 2
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 2
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 2
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 2
- 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 description 2
- RJWBTWIBUIGANW-UHFFFAOYSA-N 4-chlorobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(Cl)C=C1 RJWBTWIBUIGANW-UHFFFAOYSA-N 0.000 description 2
- BRIXOPDYGQCZFO-UHFFFAOYSA-N 4-ethylphenylsulfonic acid Chemical compound CCC1=CC=C(S(O)(=O)=O)C=C1 BRIXOPDYGQCZFO-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000012965 benzophenone Substances 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000000262 estrogen Substances 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 2
- 239000000575 pesticide Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- BPEUZDVVOMVLJJ-UHFFFAOYSA-N (2-amino-3,4-dichlorophenyl)-phenylmethanone Chemical compound NC1=C(Cl)C(Cl)=CC=C1C(=O)C1=CC=CC=C1 BPEUZDVVOMVLJJ-UHFFFAOYSA-N 0.000 description 1
- WSXPCBBBFNSXNG-UHFFFAOYSA-N (2-amino-3,5-dichlorophenyl)-phenylmethanone Chemical compound NC1=C(Cl)C=C(Cl)C=C1C(=O)C1=CC=CC=C1 WSXPCBBBFNSXNG-UHFFFAOYSA-N 0.000 description 1
- RUSKHLGGXZTJFK-UHFFFAOYSA-N (2-amino-3-bromophenyl)-phenylmethanone Chemical compound NC1=C(Br)C=CC=C1C(=O)C1=CC=CC=C1 RUSKHLGGXZTJFK-UHFFFAOYSA-N 0.000 description 1
- JCPSDGBPFXACKB-UHFFFAOYSA-N (2-amino-3-chlorophenyl)-phenylmethanone Chemical compound NC1=C(Cl)C=CC=C1C(=O)C1=CC=CC=C1 JCPSDGBPFXACKB-UHFFFAOYSA-N 0.000 description 1
- MDGVFPJJGJJBAA-UHFFFAOYSA-N (2-amino-3-fluoro-5-methylphenyl)-phenylmethanone Chemical compound CC1=CC(F)=C(N)C(C(=O)C=2C=CC=CC=2)=C1 MDGVFPJJGJJBAA-UHFFFAOYSA-N 0.000 description 1
- QMWFXOGRAIVYSX-UHFFFAOYSA-N (2-amino-3-propan-2-ylphenyl)-phenylmethanone Chemical compound CC(C)C1=CC=CC(C(=O)C=2C=CC=CC=2)=C1N QMWFXOGRAIVYSX-UHFFFAOYSA-N 0.000 description 1
- TYBSACUDUNDVDG-UHFFFAOYSA-N (2-amino-4,5-dimethylphenyl)-(4-chlorophenyl)methanone Chemical compound NC1=C(C(=O)C2=CC=C(C=C2)Cl)C=C(C(=C1)C)C TYBSACUDUNDVDG-UHFFFAOYSA-N 0.000 description 1
- NPOSTKZYBVQXNJ-UHFFFAOYSA-N (2-amino-4-bromophenyl)-phenylmethanone Chemical compound NC1=CC(Br)=CC=C1C(=O)C1=CC=CC=C1 NPOSTKZYBVQXNJ-UHFFFAOYSA-N 0.000 description 1
- PELAWRHVRDOWQT-UHFFFAOYSA-N (2-amino-4-chlorophenyl)-phenylmethanone Chemical compound NC1=CC(Cl)=CC=C1C(=O)C1=CC=CC=C1 PELAWRHVRDOWQT-UHFFFAOYSA-N 0.000 description 1
- GVTOXFDYFZNJKP-UHFFFAOYSA-N (2-amino-4-methoxyphenyl)-(2-methoxyphenyl)methanone Chemical compound NC1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1OC GVTOXFDYFZNJKP-UHFFFAOYSA-N 0.000 description 1
- DKIHAYDTTRKFDA-UHFFFAOYSA-N (2-amino-5-bromo-4-methoxyphenyl)-phenylmethanone Chemical compound NC1=C(C(=O)C2=CC=CC=C2)C=C(C(=C1)OC)Br DKIHAYDTTRKFDA-UHFFFAOYSA-N 0.000 description 1
- XCOKDXNGCQXFCV-UHFFFAOYSA-N (2-amino-5-bromophenyl)-(2-fluorophenyl)methanone Chemical compound NC1=CC=C(Br)C=C1C(=O)C1=CC=CC=C1F XCOKDXNGCQXFCV-UHFFFAOYSA-N 0.000 description 1
- VKSPFFVNEILJKO-UHFFFAOYSA-N (2-amino-5-bromophenyl)-(4-ethoxyphenyl)methanone Chemical compound C1=CC(OCC)=CC=C1C(=O)C1=CC(Br)=CC=C1N VKSPFFVNEILJKO-UHFFFAOYSA-N 0.000 description 1
- OCHXQKDWNREAJT-UHFFFAOYSA-N (2-amino-5-bromophenyl)-(4-methylphenyl)methanone Chemical compound C1=CC(C)=CC=C1C(=O)C1=CC(Br)=CC=C1N OCHXQKDWNREAJT-UHFFFAOYSA-N 0.000 description 1
- RZDLUBDXEDYULT-UHFFFAOYSA-N (2-amino-5-chlorophenyl)-(2-methoxy-5-methylphenyl)methanone Chemical compound COC1=CC=C(C)C=C1C(=O)C1=CC(Cl)=CC=C1N RZDLUBDXEDYULT-UHFFFAOYSA-N 0.000 description 1
- JBKFVAVNIDDFFD-UHFFFAOYSA-N (2-amino-5-chlorophenyl)-(4-chlorophenyl)methanone Chemical compound NC1=CC=C(Cl)C=C1C(=O)C1=CC=C(Cl)C=C1 JBKFVAVNIDDFFD-UHFFFAOYSA-N 0.000 description 1
- OYBRKOIWKRMOPW-UHFFFAOYSA-N (2-amino-5-chlorophenyl)-(4-fluorophenyl)methanone Chemical compound NC1=CC=C(Cl)C=C1C(=O)C1=CC=C(F)C=C1 OYBRKOIWKRMOPW-UHFFFAOYSA-N 0.000 description 1
- NRIUXRXDBVAPGT-UHFFFAOYSA-N (2-amino-5-chlorophenyl)-(4-methoxyphenyl)methanone Chemical compound C1=CC(OC)=CC=C1C(=O)C1=CC(Cl)=CC=C1N NRIUXRXDBVAPGT-UHFFFAOYSA-N 0.000 description 1
- ZUWXHHBROGLWNH-UHFFFAOYSA-N (2-amino-5-chlorophenyl)-phenylmethanone Chemical compound NC1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1 ZUWXHHBROGLWNH-UHFFFAOYSA-N 0.000 description 1
- UKDOBSYQTBSUQR-UHFFFAOYSA-N (2-amino-5-methoxyphenyl)-phenylmethanone Chemical compound COC1=CC=C(N)C(C(=O)C=2C=CC=CC=2)=C1 UKDOBSYQTBSUQR-UHFFFAOYSA-N 0.000 description 1
- NTGRKUAFVPVIIU-UHFFFAOYSA-N (2-amino-6-bromophenyl)-phenylmethanone Chemical compound NC1=CC=CC(Br)=C1C(=O)C1=CC=CC=C1 NTGRKUAFVPVIIU-UHFFFAOYSA-N 0.000 description 1
- IQHIGDFLXBHMCV-UHFFFAOYSA-N (2-amino-6-chlorophenyl)-phenylmethanone Chemical compound NC1=CC=CC(Cl)=C1C(=O)C1=CC=CC=C1 IQHIGDFLXBHMCV-UHFFFAOYSA-N 0.000 description 1
- NRAJMXHXQHCBHO-UHFFFAOYSA-N (2-aminophenyl)-(2-fluorophenyl)methanone Chemical compound NC1=CC=CC=C1C(=O)C1=CC=CC=C1F NRAJMXHXQHCBHO-UHFFFAOYSA-N 0.000 description 1
- WIISOMGJWLLMDG-UHFFFAOYSA-N (2-aminophenyl)-(4-bromophenyl)methanone Chemical compound NC1=CC=CC=C1C(=O)C1=CC=C(Br)C=C1 WIISOMGJWLLMDG-UHFFFAOYSA-N 0.000 description 1
- FLORUWDSYNSEAH-UHFFFAOYSA-N (2-aminophenyl)-(4-methoxyphenyl)methanone Chemical compound C1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1N FLORUWDSYNSEAH-UHFFFAOYSA-N 0.000 description 1
- CORGGHOJUZMEKZ-UHFFFAOYSA-N (6-amino-6-chlorocyclohexa-2,4-dien-1-yl)-phenylmethanone Chemical compound NC1(C(C(=O)C2=CC=CC=C2)C=CC=C1)Cl CORGGHOJUZMEKZ-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 1
- 125000006304 2-iodophenyl group Chemical group [H]C1=C([H])C(I)=C(*)C([H])=C1[H] 0.000 description 1
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 1
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 1
- PXACTUVBBMDKRW-UHFFFAOYSA-N 4-bromobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(Br)C=C1 PXACTUVBBMDKRW-UHFFFAOYSA-N 0.000 description 1
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 1
- IWYVYUZADLIDEY-UHFFFAOYSA-N 4-methoxybenzenesulfonic acid Chemical compound COC1=CC=C(S(O)(=O)=O)C=C1 IWYVYUZADLIDEY-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- DLCATLRESFSYGW-UHFFFAOYSA-N CC1(C=C(C)C=CC1N)C(C1=CC=CC=C1)=O Chemical compound CC1(C=C(C)C=CC1N)C(C1=CC=CC=C1)=O DLCATLRESFSYGW-UHFFFAOYSA-N 0.000 description 1
- 241000282421 Canidae Species 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241000272201 Columbiformes Species 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical class [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 241000287182 Sturnidae Species 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- IYFHQTVZLAPTIH-UHFFFAOYSA-N [2-amino-3-(trifluoromethyl)phenyl]-phenylmethanone Chemical compound C1=CC=C(C(F)(F)F)C(N)=C1C(=O)C1=CC=CC=C1 IYFHQTVZLAPTIH-UHFFFAOYSA-N 0.000 description 1
- PGWWMPRATGPKGO-UHFFFAOYSA-N [2-amino-4-(trifluoromethyl)phenyl]-phenylmethanone Chemical compound NC1=CC(C(F)(F)F)=CC=C1C(=O)C1=CC=CC=C1 PGWWMPRATGPKGO-UHFFFAOYSA-N 0.000 description 1
- ZMAFLDDFBUFYOF-UHFFFAOYSA-N [2-amino-5-(trifluoromethyl)phenyl]-[2-(trifluoromethyl)phenyl]methanone Chemical compound NC1=C(C(=O)C2=C(C=CC=C2)C(F)(F)F)C=C(C=C1)C(F)(F)F ZMAFLDDFBUFYOF-UHFFFAOYSA-N 0.000 description 1
- NRMOBHGSHDKJLW-UHFFFAOYSA-N [2-amino-5-(trifluoromethyl)phenyl]-phenylmethanone Chemical compound NC1=CC=C(C(F)(F)F)C=C1C(=O)C1=CC=CC=C1 NRMOBHGSHDKJLW-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- XXRGLCKZBCIEKO-DLMDZQPMSA-N azocine Chemical compound C/1=C/C=C\N=C/C=C\1 XXRGLCKZBCIEKO-DLMDZQPMSA-N 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 150000008107 benzenesulfonic acids Chemical class 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000035558 fertility Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000007902 hard capsule Substances 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- HCWCAKKEBCNQJP-UHFFFAOYSA-N magnesium orthosilicate Chemical compound [Mg+2].[Mg+2].[O-][Si]([O-])([O-])[O-] HCWCAKKEBCNQJP-UHFFFAOYSA-N 0.000 description 1
- 239000000391 magnesium silicate Substances 0.000 description 1
- 229910052919 magnesium silicate Inorganic materials 0.000 description 1
- 235000019792 magnesium silicate Nutrition 0.000 description 1
- 235000009973 maize Nutrition 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical class C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 230000004584 weight gain Effects 0.000 description 1
- 235000019786 weight gain Nutrition 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US43758865A | 1965-03-05 | 1965-03-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1620623A1 true DE1620623A1 (de) | 1969-10-23 |
Family
ID=23737060
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19661620623 Pending DE1620623A1 (de) | 1965-03-05 | 1966-02-26 | Verfahren zur Herstellung von Dibenzodiazocinen |
Country Status (5)
| Country | Link |
|---|---|
| CH (1) | CH473132A (enrdf_load_stackoverflow) |
| DE (1) | DE1620623A1 (enrdf_load_stackoverflow) |
| GB (1) | GB1125225A (enrdf_load_stackoverflow) |
| IL (1) | IL25170A (enrdf_load_stackoverflow) |
| NL (1) | NL6602819A (enrdf_load_stackoverflow) |
-
1966
- 1966-02-07 GB GB530466A patent/GB1125225A/en not_active Expired
- 1966-02-14 IL IL2517066A patent/IL25170A/xx unknown
- 1966-02-15 CH CH215566A patent/CH473132A/de not_active IP Right Cessation
- 1966-02-26 DE DE19661620623 patent/DE1620623A1/de active Pending
- 1966-03-04 NL NL6602819A patent/NL6602819A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CH473132A (de) | 1969-05-31 |
| IL25170A (en) | 1969-06-25 |
| NL6602819A (enrdf_load_stackoverflow) | 1966-09-06 |
| GB1125225A (en) | 1968-08-28 |
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