FI70010C - Foerfarande foer framstaellning av 10-oxo-10,11-dihydro-5h-dibens/b f/azepin-5-karboxamid genom omlagring av 10,11-epoxy-10,11-dihydro-5h-dibens/b f/azepin-5-karboxamid - Google Patents
Foerfarande foer framstaellning av 10-oxo-10,11-dihydro-5h-dibens/b f/azepin-5-karboxamid genom omlagring av 10,11-epoxy-10,11-dihydro-5h-dibens/b f/azepin-5-karboxamid Download PDFInfo
- Publication number
- FI70010C FI70010C FI791233A FI791233A FI70010C FI 70010 C FI70010 C FI 70010C FI 791233 A FI791233 A FI 791233A FI 791233 A FI791233 A FI 791233A FI 70010 C FI70010 C FI 70010C
- Authority
- FI
- Finland
- Prior art keywords
- dihydro
- carboxamide
- dibens
- azepin
- oxo
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 8
- ZFXVFMBOFIEPII-UHFFFAOYSA-N 1h-azepine-4-carboxamide Chemical compound NC(=O)C1=CC=CNC=C1 ZFXVFMBOFIEPII-UHFFFAOYSA-N 0.000 title claims description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 30
- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Inorganic materials [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 claims description 19
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 16
- 229910001868 water Inorganic materials 0.000 claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 9
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 8
- CTRLABGOLIVAIY-UHFFFAOYSA-N oxcarbazepine Chemical compound C1C(=O)C2=CC=CC=C2N(C(=O)N)C2=CC=CC=C21 CTRLABGOLIVAIY-UHFFFAOYSA-N 0.000 claims description 7
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 6
- 229910001622 calcium bromide Inorganic materials 0.000 claims description 6
- WGEFECGEFUFIQW-UHFFFAOYSA-L calcium dibromide Chemical compound [Ca+2].[Br-].[Br-] WGEFECGEFUFIQW-UHFFFAOYSA-L 0.000 claims description 6
- 229910001623 magnesium bromide Inorganic materials 0.000 claims description 6
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 claims description 5
- 150000004677 hydrates Chemical class 0.000 claims description 5
- 238000006462 rearrangement reaction Methods 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- 239000011777 magnesium Substances 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 3
- 229940046413 calcium iodide Drugs 0.000 claims description 3
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 3
- 229910001509 metal bromide Inorganic materials 0.000 claims description 2
- 229910001511 metal iodide Inorganic materials 0.000 claims description 2
- 230000008707 rearrangement Effects 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
- 238000010992 reflux Methods 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- -1 aliphatic epoxides Chemical class 0.000 description 3
- XLYOFNOQVPJJNP-ZSJDYOACSA-N heavy water Substances [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 3
- MHCFAGZWMAWTNR-UHFFFAOYSA-M lithium perchlorate Chemical compound [Li+].[O-]Cl(=O)(=O)=O MHCFAGZWMAWTNR-UHFFFAOYSA-M 0.000 description 3
- 229910001486 lithium perchlorate Inorganic materials 0.000 description 3
- OTCKOJUMXQWKQG-UHFFFAOYSA-L magnesium bromide Chemical compound [Mg+2].[Br-].[Br-] OTCKOJUMXQWKQG-UHFFFAOYSA-L 0.000 description 3
- 229910001641 magnesium iodide Inorganic materials 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- LFSAPCRASZRSKS-UHFFFAOYSA-N 2-methylcyclohexan-1-one Chemical compound CC1CCCCC1=O LFSAPCRASZRSKS-UHFFFAOYSA-N 0.000 description 2
- FIEKVYPYFQSFTP-UHFFFAOYSA-N 6-methyl-7-oxabicyclo[4.1.0]heptane Chemical compound C1CCCC2OC21C FIEKVYPYFQSFTP-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- CGZZMOTZOONQIA-UHFFFAOYSA-N cycloheptanone Chemical compound O=C1CCCCCC1 CGZZMOTZOONQIA-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- ZWAJLVLEBYIOTI-UHFFFAOYSA-N cyclohexene oxide Chemical compound C1CCCC2OC21 ZWAJLVLEBYIOTI-UHFFFAOYSA-N 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- 238000006317 isomerization reaction Methods 0.000 description 2
- HSZCZNFXUDYRKD-UHFFFAOYSA-M lithium iodide Chemical compound [Li+].[I-] HSZCZNFXUDYRKD-UHFFFAOYSA-M 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 235000009518 sodium iodide Nutrition 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 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 2
- WNEUNPWLVWPBGB-UHFFFAOYSA-N 1,6-dimethyl-7-oxabicyclo[4.1.0]heptane Chemical compound C1CCCC2(C)OC21C WNEUNPWLVWPBGB-UHFFFAOYSA-N 0.000 description 1
- MNZAKDODWSQONA-UHFFFAOYSA-N 1-dibutylphosphorylbutane Chemical compound CCCCP(=O)(CCCC)CCCC MNZAKDODWSQONA-UHFFFAOYSA-N 0.000 description 1
- MLOZFLXCWGERSM-UHFFFAOYSA-N 8-oxabicyclo[5.1.0]octane Chemical compound C1CCCCC2OC21 MLOZFLXCWGERSM-UHFFFAOYSA-N 0.000 description 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical class CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- WUSJALRVWRGZMI-UHFFFAOYSA-L calcium;diiodide;tetrahydrate Chemical compound O.O.O.O.[Ca+2].[I-].[I-] WUSJALRVWRGZMI-UHFFFAOYSA-L 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohexene oxide Natural products O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- 150000004694 iodide salts Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- UPZGJLYTRBYTLM-UHFFFAOYSA-M lithium;iodide;dihydrate Chemical compound [Li+].O.O.[I-] UPZGJLYTRBYTLM-UHFFFAOYSA-M 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- NUJGJRNETVAIRJ-UHFFFAOYSA-N octanal Chemical compound CCCCCCCC=O NUJGJRNETVAIRJ-UHFFFAOYSA-N 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/02—Magnesium compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Epoxy Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH413478A CH633271A5 (en) | 1978-04-18 | 1978-04-18 | Process for the rearrangement of 10,11-epoxy-10,11-dihydro-5H-dibenz[b,f]azepines to give 10-oxo-10,11-dihydro-5H-dibenz(b,f)azepines |
| CH413478 | 1978-04-18 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI791233A7 FI791233A7 (fi) | 1979-10-19 |
| FI70010B FI70010B (fi) | 1986-01-31 |
| FI70010C true FI70010C (fi) | 1986-09-12 |
Family
ID=4270467
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI791233A FI70010C (fi) | 1978-04-18 | 1979-04-17 | Foerfarande foer framstaellning av 10-oxo-10,11-dihydro-5h-dibens/b f/azepin-5-karboxamid genom omlagring av 10,11-epoxy-10,11-dihydro-5h-dibens/b f/azepin-5-karboxamid |
Country Status (17)
| Country | Link |
|---|---|
| JP (1) | JPS54138588A (de) |
| AR (1) | AR222329A1 (de) |
| AT (1) | AT373877B (de) |
| BG (1) | BG29282A3 (de) |
| CA (1) | CA1112241A (de) |
| CH (1) | CH633271A5 (de) |
| DK (1) | DK157779A (de) |
| ES (1) | ES479600A1 (de) |
| FI (1) | FI70010C (de) |
| GR (1) | GR72260B (de) |
| HU (1) | HU182477B (de) |
| NL (1) | NL7902811A (de) |
| NO (1) | NO149776C (de) |
| PL (1) | PL214954A1 (de) |
| PT (1) | PT69495A (de) |
| SE (1) | SE7903328L (de) |
| YU (1) | YU91779A (de) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0112812D0 (en) * | 2001-05-25 | 2001-07-18 | Portela & Ca Sa | Mthd for preparation of 10, 11-dihydro-10-hydroxy-5H-dibenz/B,F/azepine-5-c arboxamide and 10,11-dihydro-10-oxo-5H-dibenz/B,F/azepine-5-carb oxamide therefrom |
| CA2471666C (en) | 2004-06-18 | 2009-10-13 | Apotex Pharmachem Inc. | An improved process for the preparation of oxcarbazepine and related intermediates |
| GB2422149A (en) | 2005-01-14 | 2006-07-19 | Portela & Ca Sa | Process for the preparation of 10,11-dihydro-10-hydroxy-5H-dibenz[b,f]azepine-5-carboxamide |
-
1978
- 1978-04-18 CH CH413478A patent/CH633271A5/de not_active IP Right Cessation
-
1979
- 1979-04-07 GR GR58835A patent/GR72260B/el unknown
- 1979-04-10 NL NL7902811A patent/NL7902811A/xx not_active Application Discontinuation
- 1979-04-12 CA CA325,802A patent/CA1112241A/en not_active Expired
- 1979-04-16 BG BG043253A patent/BG29282A3/xx unknown
- 1979-04-16 ES ES479600A patent/ES479600A1/es not_active Expired
- 1979-04-16 AR AR276195A patent/AR222329A1/es active
- 1979-04-17 PT PT69495A patent/PT69495A/pt unknown
- 1979-04-17 DK DK157779A patent/DK157779A/da not_active IP Right Cessation
- 1979-04-17 YU YU00917/79A patent/YU91779A/xx unknown
- 1979-04-17 AT AT0288379A patent/AT373877B/de not_active IP Right Cessation
- 1979-04-17 HU HU79CI1926A patent/HU182477B/hu unknown
- 1979-04-17 SE SE7903328A patent/SE7903328L/xx not_active Application Discontinuation
- 1979-04-17 NO NO791274A patent/NO149776C/no unknown
- 1979-04-17 PL PL21495479A patent/PL214954A1/xx unknown
- 1979-04-17 FI FI791233A patent/FI70010C/fi not_active IP Right Cessation
- 1979-04-18 JP JP4680279A patent/JPS54138588A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| ES479600A1 (es) | 1979-07-16 |
| SE7903328L (sv) | 1979-10-19 |
| PT69495A (en) | 1979-05-01 |
| BG29282A3 (bg) | 1980-10-15 |
| YU91779A (en) | 1983-01-21 |
| HU182477B (en) | 1984-01-30 |
| DK157779A (da) | 1979-10-19 |
| ATA288379A (de) | 1983-07-15 |
| NO149776B (no) | 1984-03-12 |
| JPS54138588A (en) | 1979-10-27 |
| PL214954A1 (de) | 1980-07-01 |
| GR72260B (de) | 1983-10-10 |
| AR222329A1 (es) | 1981-05-15 |
| CH633271A5 (en) | 1982-11-30 |
| NO791274L (no) | 1979-10-19 |
| NL7902811A (nl) | 1979-10-22 |
| FI70010B (fi) | 1986-01-31 |
| FI791233A7 (fi) | 1979-10-19 |
| AT373877B (de) | 1984-02-27 |
| NO149776C (no) | 1984-06-20 |
| CA1112241A (en) | 1981-11-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: CIBA-GEIGY AG |