CH642950A5 - Process for the preparation of 10-oxo-10,11-dihydro-5H-dibenz[b,f]azepine-5-carboxamide - Google Patents
Process for the preparation of 10-oxo-10,11-dihydro-5H-dibenz[b,f]azepine-5-carboxamide Download PDFInfo
- Publication number
- CH642950A5 CH642950A5 CH970479A CH970479A CH642950A5 CH 642950 A5 CH642950 A5 CH 642950A5 CH 970479 A CH970479 A CH 970479A CH 970479 A CH970479 A CH 970479A CH 642950 A5 CH642950 A5 CH 642950A5
- Authority
- CH
- Switzerland
- Prior art keywords
- dibenz
- carboxamide
- sulfuric acid
- dihydro
- oxo
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 30
- 238000002360 preparation method Methods 0.000 title claims description 9
- CTRLABGOLIVAIY-UHFFFAOYSA-N oxcarbazepine Chemical compound C1C(=O)C2=CC=CC=C2N(C(=O)N)C2=CC=CC=C21 CTRLABGOLIVAIY-UHFFFAOYSA-N 0.000 title abstract 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 47
- 150000001875 compounds Chemical class 0.000 claims abstract description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 24
- 238000006243 chemical reaction Methods 0.000 claims description 16
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 12
- 239000007858 starting material Substances 0.000 claims description 12
- 230000007062 hydrolysis Effects 0.000 claims description 10
- 238000006460 hydrolysis reaction Methods 0.000 claims description 10
- 239000000243 solution Substances 0.000 claims description 10
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 8
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 8
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 claims description 8
- 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 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 235000019253 formic acid Nutrition 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims description 4
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 4
- 229910021529 ammonia Inorganic materials 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 150000007530 organic bases Chemical group 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 claims description 2
- GWEHVDNNLFDJLR-UHFFFAOYSA-N 1,3-diphenylurea Chemical compound C=1C=CC=CC=1NC(=O)NC1=CC=CC=C1 GWEHVDNNLFDJLR-UHFFFAOYSA-N 0.000 claims description 2
- SGUVLZREKBPKCE-UHFFFAOYSA-N 1,5-diazabicyclo[4.3.0]-non-5-ene Chemical compound C1CCN=C2CCCN21 SGUVLZREKBPKCE-UHFFFAOYSA-N 0.000 claims description 2
- ZFXVFMBOFIEPII-UHFFFAOYSA-N 1h-azepine-4-carboxamide Chemical compound NC(=O)C1=CC=CNC=C1 ZFXVFMBOFIEPII-UHFFFAOYSA-N 0.000 claims description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 2
- JDAZPRYNBAKNQG-UHFFFAOYSA-N CCOC(=O)C(=O)C(CC(=C)Cl)C1=C(C(=CC=C1)Cl)[N+](=O)[O-] Chemical compound CCOC(=O)C(=O)C(CC(=C)Cl)C1=C(C(=CC=C1)Cl)[N+](=O)[O-] JDAZPRYNBAKNQG-UHFFFAOYSA-N 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 239000011260 aqueous acid Substances 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 150000003857 carboxamides Chemical class 0.000 claims description 2
- VHLNQRWKNKQLAR-UHFFFAOYSA-N ethyl 3-(3-chloro-2-nitrophenyl)-2,5-dioxohexanoate Chemical compound CCOC(=O)C(=O)C(CC(C)=O)c1cccc(Cl)c1[N+]([O-])=O VHLNQRWKNKQLAR-UHFFFAOYSA-N 0.000 claims description 2
- 125000000524 functional group Chemical group 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 230000000269 nucleophilic effect Effects 0.000 claims description 2
- 239000012074 organic phase Substances 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 claims description 2
- 239000011780 sodium chloride Substances 0.000 claims description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 claims description 2
- 235000011152 sodium sulphate Nutrition 0.000 claims description 2
- 238000003756 stirring Methods 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- -1 sulfuric acid Ketone Chemical class 0.000 claims description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 2
- 150000003672 ureas Chemical class 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- HQXOFJNTUXHWMC-UHFFFAOYSA-N 5-chlorobenzo[b][1]benzazepine-11-carboxamide Chemical compound C1=C(Cl)C2=CC=CC=C2N(C(=O)N)C2=CC=CC=C21 HQXOFJNTUXHWMC-UHFFFAOYSA-N 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 0.000 abstract 1
- 239000001117 sulphuric acid Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/14—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D223/18—Dibenzazepines; Hydrogenated dibenzazepines
- C07D223/22—Dibenz [b, f] azepines; Hydrogenated dibenz [b, f] azepines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Hydrogenated Pyridines (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH970479A CH642950A5 (en) | 1979-10-30 | 1979-10-30 | Process for the preparation of 10-oxo-10,11-dihydro-5H-dibenz[b,f]azepine-5-carboxamide |
| ES496332A ES8200097A1 (es) | 1979-10-30 | 1980-10-28 | Procedimiento para la obtencion de 10-oxo-10-11,dihidro-5h- dibenz(b,f)azepin-3-carboxamida |
| NO803229A NO153368C (no) | 1979-10-30 | 1980-10-29 | Fremgangsmaate til fremstilling av 10-okso-10,11-dihydro-5h-dibenz(b,f)-asepin-5-karboksamid. |
| SE8007597A SE447106B (sv) | 1979-10-30 | 1980-10-29 | Forfarande for framstellning av 10-oxo-10, 11-dihydro-5h-dibens /b,f/azepin-5-karboxamid |
| AT0531980A AT375926B (de) | 1979-10-30 | 1980-10-29 | Verfahren zur herstellung von 10-oxo-10,11-dihydro-5h-dibenz(b,f)azepin-5carboxamid |
| DK457680A DK457680A (da) | 1979-10-30 | 1980-10-29 | Fremgangsmaade til fremstilling af et urinstofderivat |
| JP15152580A JPS5673066A (en) | 1979-10-30 | 1980-10-30 | Manufacture of urea derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH970479A CH642950A5 (en) | 1979-10-30 | 1979-10-30 | Process for the preparation of 10-oxo-10,11-dihydro-5H-dibenz[b,f]azepine-5-carboxamide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH642950A5 true CH642950A5 (en) | 1984-05-15 |
Family
ID=4354741
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH970479A CH642950A5 (en) | 1979-10-30 | 1979-10-30 | Process for the preparation of 10-oxo-10,11-dihydro-5H-dibenz[b,f]azepine-5-carboxamide |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS5673066A (es) |
| AT (1) | AT375926B (es) |
| CH (1) | CH642950A5 (es) |
| DK (1) | DK457680A (es) |
| ES (1) | ES8200097A1 (es) |
| NO (1) | NO153368C (es) |
| SE (1) | SE447106B (es) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002096881A1 (en) * | 2001-05-25 | 2002-12-05 | Portela & Ca Sa | Method for preparation of 10,11-dihydro-10-hydroxy-5h-dibenz/b,f/azepine-5-carboxamide and 10,11-dihydro-10-0x0-5h-dibenz/b,f/azepine-5-carboxamide |
| WO2007141798A1 (en) * | 2006-06-07 | 2007-12-13 | Jubilant Organosys Limited | Process for producing oxcarbazepine via an 11-alkoxy-10-halo-dihydroiminostilbene intermediate |
| US7834177B2 (en) | 2005-01-14 | 2010-11-16 | Bial - Portela & Ca, S.A. | Method for preparation of 10,11-dihydro-10-hydroxy-5H-dibenz/b,f/azepine-5-carboxamide |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2401605A (en) | 2003-05-12 | 2004-11-17 | Portela & Ca Sa | Method for racemisation of (S)-(+)- and (R)-(-)-10,11-dihydro-10-hydroxy-5H-dibenz[b,f]azepine-5-carboxamide and optically enriched mixtures thereof |
-
1979
- 1979-10-30 CH CH970479A patent/CH642950A5/de not_active IP Right Cessation
-
1980
- 1980-10-28 ES ES496332A patent/ES8200097A1/es not_active Expired
- 1980-10-29 SE SE8007597A patent/SE447106B/sv not_active IP Right Cessation
- 1980-10-29 NO NO803229A patent/NO153368C/no unknown
- 1980-10-29 AT AT0531980A patent/AT375926B/de not_active IP Right Cessation
- 1980-10-29 DK DK457680A patent/DK457680A/da not_active Application Discontinuation
- 1980-10-30 JP JP15152580A patent/JPS5673066A/ja active Pending
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002096881A1 (en) * | 2001-05-25 | 2002-12-05 | Portela & Ca Sa | Method for preparation of 10,11-dihydro-10-hydroxy-5h-dibenz/b,f/azepine-5-carboxamide and 10,11-dihydro-10-0x0-5h-dibenz/b,f/azepine-5-carboxamide |
| US7241886B2 (en) | 2001-05-25 | 2007-07-10 | Portela & C.A., S.A. | Method for preparation of 10,11-dihydro-10-hydroxy-5h-dibenz/b, f/azepine-5-carboxamide and 10,11-dihydro-10-oxo-5h-dibenz/b, f/azepine-5-carboxamide |
| EP1958938A3 (en) * | 2001-05-25 | 2008-09-03 | BIAL - Portela & Ca., S.A. | A process for the preparation of 10,11-dihydro-10-oxo-5H-dibenz[b,f]azepine-5-carboxamide |
| AU2007221834B2 (en) * | 2001-05-25 | 2009-02-05 | Bial - Portela & Ca., S.A. | Method for preparation of 10,11-dihydro-10-hydroxy-5H-dibenz/b,f/azepine-5-carboxamide and 10,11-dihydro-10-oxo-5H-dibenz/b,f/azepine-5-carboxamide |
| US7834177B2 (en) | 2005-01-14 | 2010-11-16 | Bial - Portela & Ca, S.A. | Method for preparation of 10,11-dihydro-10-hydroxy-5H-dibenz/b,f/azepine-5-carboxamide |
| WO2007141798A1 (en) * | 2006-06-07 | 2007-12-13 | Jubilant Organosys Limited | Process for producing oxcarbazepine via an 11-alkoxy-10-halo-dihydroiminostilbene intermediate |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5673066A (en) | 1981-06-17 |
| SE447106B (sv) | 1986-10-27 |
| DK457680A (da) | 1981-05-01 |
| ES496332A0 (es) | 1981-10-16 |
| NO153368B (no) | 1985-11-25 |
| NO153368C (no) | 1986-03-05 |
| ES8200097A1 (es) | 1981-10-16 |
| ATA531980A (de) | 1984-02-15 |
| AT375926B (de) | 1984-09-25 |
| NO803229L (no) | 1981-05-04 |
| SE8007597L (sv) | 1981-05-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |