DD294247A5 - Verbessertes verfahren zur herstellung von 5h-dibenz[b,f]azepin - Google Patents
Verbessertes verfahren zur herstellung von 5h-dibenz[b,f]azepin Download PDFInfo
- Publication number
- DD294247A5 DD294247A5 DD90340402A DD34040290A DD294247A5 DD 294247 A5 DD294247 A5 DD 294247A5 DD 90340402 A DD90340402 A DD 90340402A DD 34040290 A DD34040290 A DD 34040290A DD 294247 A5 DD294247 A5 DD 294247A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- boiling
- solvent
- mol
- polar protic
- reaction
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 20
- LCGTWRLJTMHIQZ-UHFFFAOYSA-N 5H-dibenzo[b,f]azepine Chemical compound C1=CC2=CC=CC=C2NC2=CC=CC=C21 LCGTWRLJTMHIQZ-UHFFFAOYSA-N 0.000 title claims abstract description 14
- 238000002360 preparation method Methods 0.000 title claims abstract description 7
- 238000009835 boiling Methods 0.000 claims abstract description 25
- 239000003054 catalyst Substances 0.000 claims abstract description 22
- 238000006243 chemical reaction Methods 0.000 claims abstract description 19
- 239000002904 solvent Substances 0.000 claims abstract description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 16
- 239000001257 hydrogen Substances 0.000 claims abstract description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 15
- 239000003586 protic polar solvent Substances 0.000 claims abstract description 13
- 238000006356 dehydrogenation reaction Methods 0.000 claims abstract description 8
- 239000000203 mixture Substances 0.000 claims abstract description 8
- 230000003197 catalytic effect Effects 0.000 claims abstract description 6
- 229910000510 noble metal Inorganic materials 0.000 claims abstract description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- MHCVCKDNQYMGEX-UHFFFAOYSA-N 1,1'-biphenyl;phenoxybenzene Chemical group C1=CC=CC=C1C1=CC=CC=C1.C=1C=CC=CC=1OC1=CC=CC=C1 MHCVCKDNQYMGEX-UHFFFAOYSA-N 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 4
- XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 claims description 3
- 150000001555 benzenes Chemical class 0.000 claims description 3
- 150000002828 nitro derivatives Chemical class 0.000 claims description 2
- 229920001223 polyethylene glycol Polymers 0.000 claims description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- 235000013322 soy milk Nutrition 0.000 claims 1
- ZSMRRZONCYIFNB-UHFFFAOYSA-N 6,11-dihydro-5h-benzo[b][1]benzazepine Chemical group C1CC2=CC=CC=C2NC2=CC=CC=C12 ZSMRRZONCYIFNB-UHFFFAOYSA-N 0.000 abstract description 16
- 239000000155 melt Substances 0.000 abstract description 8
- 239000007791 liquid phase Substances 0.000 abstract description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 239000000047 product Substances 0.000 description 16
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 10
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 7
- 229910052763 palladium Inorganic materials 0.000 description 6
- 230000035484 reaction time Effects 0.000 description 6
- 238000000354 decomposition reaction Methods 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 231100000572 poisoning Toxicity 0.000 description 4
- 230000000607 poisoning effect Effects 0.000 description 4
- PLAZTCDQAHEYBI-UHFFFAOYSA-N 2-nitrotoluene Chemical compound CC1=CC=CC=C1[N+]([O-])=O PLAZTCDQAHEYBI-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 239000012454 non-polar solvent Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- WDCYWAQPCXBPJA-UHFFFAOYSA-N 1,3-dinitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC([N+]([O-])=O)=C1 WDCYWAQPCXBPJA-UHFFFAOYSA-N 0.000 description 1
- LWHDQPLUIFIFFT-UHFFFAOYSA-N 2,3,5,6-tetrabromocyclohexa-2,5-diene-1,4-dione Chemical compound BrC1=C(Br)C(=O)C(Br)=C(Br)C1=O LWHDQPLUIFIFFT-UHFFFAOYSA-N 0.000 description 1
- BWHOZHOGCMHOBV-UHFFFAOYSA-N Benzalacetone Natural products CC(=O)C=CC1=CC=CC=C1 BWHOZHOGCMHOBV-UHFFFAOYSA-N 0.000 description 1
- DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 description 1
- IEPRKVQEAMIZSS-UHFFFAOYSA-N Di-Et ester-Fumaric acid Natural products CCOC(=O)C=CC(=O)OCC IEPRKVQEAMIZSS-UHFFFAOYSA-N 0.000 description 1
- IEPRKVQEAMIZSS-WAYWQWQTSA-N Diethyl maleate Chemical compound CCOC(=O)\C=C/C(=O)OCC IEPRKVQEAMIZSS-WAYWQWQTSA-N 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000003795 desorption Methods 0.000 description 1
- 229940093476 ethylene glycol Drugs 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 238000002955 isolation Methods 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
- VLZLOWPYUQHHCG-UHFFFAOYSA-N nitromethylbenzene Chemical class [O-][N+](=O)CC1=CC=CC=C1 VLZLOWPYUQHHCG-UHFFFAOYSA-N 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 238000002336 sorption--desorption measurement Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- BWHOZHOGCMHOBV-BQYQJAHWSA-N trans-benzylideneacetone Chemical compound CC(=O)\C=C\C1=CC=CC=C1 BWHOZHOGCMHOBV-BQYQJAHWSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU892158A HU206682B (en) | 1989-05-04 | 1989-05-04 | Improved process for producing 5h-dibenz/b,f/azepine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD294247A5 true DD294247A5 (de) | 1991-09-26 |
Family
ID=10958059
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD90340402A DD294247A5 (de) | 1989-05-04 | 1990-05-04 | Verbessertes verfahren zur herstellung von 5h-dibenz[b,f]azepin |
Country Status (9)
| Country | Link |
|---|---|
| EP (1) | EP0396134A1 (pl) |
| JP (1) | JPH0356465A (pl) |
| KR (1) | KR930011490B1 (pl) |
| DD (1) | DD294247A5 (pl) |
| HU (1) | HU206682B (pl) |
| IL (1) | IL94271A (pl) |
| PL (1) | PL163638B1 (pl) |
| RU (1) | RU1797609C (pl) |
| YU (1) | YU47006B (pl) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU663580B2 (en) * | 1992-05-13 | 1995-10-12 | Novartis Ag | Preparation of iminostilbene by high-temperature dehydrogenation |
| AT401772B (de) * | 1994-12-27 | 1996-11-25 | Chemie Linz Gmbh | Verfahren zur reinigung von 5h-dibenzo-(b,f)-azepin |
| AT409628B (de) * | 2000-04-10 | 2002-09-25 | Dsm Fine Chem Austria Gmbh | Reinigungsverfahren zur herstellung von hochreinem 5h-dibenzo-(b,f)-azepin |
| CN101307021B (zh) * | 2008-07-04 | 2010-06-23 | 浙江工业大学 | 一种亚氨基芪的化学合成方法 |
| CN105439954A (zh) * | 2014-09-25 | 2016-03-30 | 中国石油化工股份有限公司 | 一种亚氨基芪的单步合成方法 |
| CN105566223A (zh) * | 2014-10-17 | 2016-05-11 | 中国石油化工股份有限公司 | 一种亚氨基芪粗品重结晶方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3074931A (en) * | 1963-01-22 | Dibenzazepines | ||
| FI74276C (fi) * | 1986-03-14 | 1988-01-11 | Orion Yhtymae Oy | Ett nytt foerfarande foer framstaellning av 5h-dibenso-(b, f)-azepin. |
-
1989
- 1989-05-04 HU HU892158A patent/HU206682B/hu not_active IP Right Cessation
-
1990
- 1990-05-02 PL PL90285047A patent/PL163638B1/pl unknown
- 1990-05-03 KR KR1019900006244A patent/KR930011490B1/ko not_active Expired - Lifetime
- 1990-05-03 IL IL9427190A patent/IL94271A/xx unknown
- 1990-05-04 RU SU904830088A patent/RU1797609C/ru active
- 1990-05-04 EP EP90108372A patent/EP0396134A1/de not_active Ceased
- 1990-05-04 YU YU197190A patent/YU47006B/sh unknown
- 1990-05-04 DD DD90340402A patent/DD294247A5/de not_active IP Right Cessation
- 1990-05-07 JP JP2115944A patent/JPH0356465A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| PL285047A1 (en) | 1991-01-14 |
| IL94271A (en) | 1994-04-12 |
| PL163638B1 (pl) | 1994-04-29 |
| HUT54994A (en) | 1991-04-29 |
| KR930011490B1 (ko) | 1993-12-08 |
| JPH0356465A (ja) | 1991-03-12 |
| HU206682B (en) | 1992-12-28 |
| RU1797609C (ru) | 1993-02-23 |
| IL94271A0 (en) | 1991-03-10 |
| EP0396134A1 (de) | 1990-11-07 |
| YU47006B (sh) | 1994-11-15 |
| KR900018038A (ko) | 1990-12-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EP | Request for examination under paragraph 12(1) filed | ||
| ENJ | Ceased due to non-payment of renewal fee |