CA1081240A - Preparation of 6,11-dihydro-11-oxodibenz (b-e)-oxepin-alkanoic acids - Google Patents
Preparation of 6,11-dihydro-11-oxodibenz (b-e)-oxepin-alkanoic acidsInfo
- Publication number
- CA1081240A CA1081240A CA243,400A CA243400A CA1081240A CA 1081240 A CA1081240 A CA 1081240A CA 243400 A CA243400 A CA 243400A CA 1081240 A CA1081240 A CA 1081240A
- Authority
- CA
- Canada
- Prior art keywords
- chloride
- temperature
- diacid
- halide
- acid
- 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.)
- Expired
Links
- 239000002253 acid Substances 0.000 title claims abstract description 28
- 238000002360 preparation method Methods 0.000 title claims abstract description 7
- 150000007513 acids Chemical class 0.000 title abstract description 10
- 238000000034 method Methods 0.000 claims abstract description 38
- 150000004820 halides Chemical class 0.000 claims description 22
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 16
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 14
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 12
- 238000005727 Friedel-Crafts reaction Methods 0.000 claims description 10
- 239000002841 Lewis acid Substances 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 150000007517 lewis acids Chemical class 0.000 claims description 9
- 239000011541 reaction mixture Substances 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052742 iron Inorganic materials 0.000 claims description 6
- 229910021578 Iron(III) chloride Inorganic materials 0.000 claims description 5
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims description 5
- MSABOFMROKLSRD-UHFFFAOYSA-N [Fe].S(=O)(Cl)Cl Chemical compound [Fe].S(=O)(Cl)Cl MSABOFMROKLSRD-UHFFFAOYSA-N 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 239000000460 chlorine Chemical group 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical group ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 3
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
- 229910052731 fluorine Chemical group 0.000 claims description 2
- 239000011737 fluorine Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- 230000000202 analgesic effect Effects 0.000 abstract description 2
- 230000003110 anti-inflammatory effect Effects 0.000 abstract 1
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Substances ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- OKNAWFBIOJJTDV-UHFFFAOYSA-N 2-(oxepin-2-yl)acetic acid Chemical compound OC(=O)CC1=CC=CC=CO1 OKNAWFBIOJJTDV-UHFFFAOYSA-N 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 229940063656 aluminum chloride Drugs 0.000 description 4
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 3
- 239000012455 biphasic mixture Substances 0.000 description 3
- 239000003518 caustics Substances 0.000 description 3
- 239000003610 charcoal Substances 0.000 description 3
- 239000011968 lewis acid catalyst Substances 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 238000007363 ring formation reaction Methods 0.000 description 3
- 238000004809 thin layer chromatography Methods 0.000 description 3
- BCYWXPITXHFIQM-UHFFFAOYSA-N 2-[[4-(carboxymethyl)phenoxy]methyl]benzoic acid Chemical compound C1=CC(CC(=O)O)=CC=C1OCC1=CC=CC=C1C(O)=O BCYWXPITXHFIQM-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000005909 Kieselgur Substances 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 208000036366 Sensation of pressure Diseases 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 230000003466 anti-cipated effect Effects 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 229960003424 phenylacetic acid Drugs 0.000 description 2
- 239000003279 phenylacetic acid Substances 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- MIMZGFBPGISKHQ-UHFFFAOYSA-N 2-(oxepin-3-yl)acetic acid Chemical compound OC(=O)CC1=COC=CC=C1 MIMZGFBPGISKHQ-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical group [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- 238000010917 Friedel-Crafts cyclization Methods 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 101150050280 alsD gene Proteins 0.000 description 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N ferric oxide Chemical compound O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 238000003402 intramolecular cyclocondensation reaction Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- ATYBXHSAIOKLMG-UHFFFAOYSA-N oxepin Chemical compound O1C=CC=CC=C1 ATYBXHSAIOKLMG-UHFFFAOYSA-N 0.000 description 1
- 150000002920 oxepines Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- -1 thionyl halide Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D313/00—Heterocyclic compounds containing rings of more than six members having one oxygen atom as the only ring hetero atom
- C07D313/02—Seven-membered rings
- C07D313/06—Seven-membered rings condensed with carbocyclic rings or ring systems
- C07D313/10—Seven-membered rings condensed with carbocyclic rings or ring systems condensed with two six-membered rings
- C07D313/12—[b,e]-condensed
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyrane Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US54096375A | 1975-01-14 | 1975-01-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1081240A true CA1081240A (en) | 1980-07-08 |
Family
ID=24157637
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA243,400A Expired CA1081240A (en) | 1975-01-14 | 1976-01-13 | Preparation of 6,11-dihydro-11-oxodibenz (b-e)-oxepin-alkanoic acids |
Country Status (20)
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS56156273A (en) * | 1980-03-31 | 1981-12-02 | Dainippon Pharmaceut Co Ltd | Acetic derivative |
| US4515946A (en) * | 1981-12-23 | 1985-05-07 | Hoechst-Roussel Pharmaceuticals Inc. | 6,11-Dihydro-11-oxo-dibenz-[b,e]oxepin derivatives |
| US4576960A (en) * | 1981-12-23 | 1986-03-18 | Hoechst Roussel Pharmaceuticals Incorporated | 6,11-Dihydro-11-oxo-dibenz[b,e]oxepin derivatives |
| US4526891A (en) * | 1983-03-10 | 1985-07-02 | Hoechst Roussel Pharmaceuticals Inc. | Substituted alkyl amine derivatives of 6,11-dihydro-11-oxodibenz[b,e]oxepins |
| WO2003082802A1 (en) * | 2002-03-27 | 2003-10-09 | Smithkline Beecham Corporation | Acid and ester compounds and methods of using the same |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1279682B (de) * | 1961-08-12 | 1968-10-10 | Boehringer & Soehne Gmbh | Verfahren zur Herstellung von 6, 11-Dihydro-dibenzo-[b, e]-oxepin- bzw. -thiepin-11-on |
| DE1294970B (de) * | 1961-09-28 | 1969-05-14 | Boehringer & Soehne Gmbh | Verfahren zur Herstellung von substituierten 6, 11-Dihydrodibenzo[b, e]-oxepin- bzw.-thiepin-11-onen |
| FR1449569A (fr) * | 1961-10-07 | 1966-05-06 | Boehringer & Soehne Gmbh | Procédé pour la préparation de dérivés basiques de la dibenzo-oxépine et de ladibenzo-thiépine, de leurs sels et de leurs composés d'ammonium quaternaire |
| YU204274A (en) * | 1973-07-24 | 1982-06-30 | Hoechst Ag | Process for preparing new dibenzoxepin derivatives |
-
1976
- 1976-01-08 ES ES444144A patent/ES444144A1/es not_active Expired
- 1976-01-09 NL NL7600204A patent/NL7600204A/xx not_active Application Discontinuation
- 1976-01-12 FI FI760052A patent/FI760052A7/fi not_active Application Discontinuation
- 1976-01-12 IT IT19179/76A patent/IT1054782B/it active
- 1976-01-13 CS CS76222A patent/CS190509B2/cs unknown
- 1976-01-13 PT PT64691A patent/PT64691B/pt unknown
- 1976-01-13 DK DK12376*#A patent/DK12376A/da not_active Application Discontinuation
- 1976-01-13 HU HU76HO1871A patent/HU175610B/hu unknown
- 1976-01-13 CA CA243,400A patent/CA1081240A/en not_active Expired
- 1976-01-13 LU LU74174A patent/LU74174A1/xx unknown
- 1976-01-13 IE IE54/76A patent/IE41999B1/en unknown
- 1976-01-13 GB GB1181/76A patent/GB1538775A/en not_active Expired
- 1976-01-13 CS CS777409A patent/CS190550B2/cs unknown
- 1976-01-13 CH CH33876A patent/CH627464A5/de not_active IP Right Cessation
- 1976-01-13 AT AT17476A patent/AT362376B/de not_active IP Right Cessation
- 1976-01-13 NO NO760101A patent/NO149387C/no unknown
- 1976-01-14 SE SE7600321A patent/SE422796B/xx unknown
- 1976-01-14 BE BE163509A patent/BE837561A/xx not_active IP Right Cessation
- 1976-01-14 MX MX762392U patent/MX3745E/es unknown
- 1976-01-14 FR FR7600784A patent/FR2297852A1/fr active Granted
- 1976-01-14 JP JP51003719A patent/JPS5195085A/ja active Pending
-
1981
- 1981-04-24 NO NO811390A patent/NO150157C/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IE41999L (en) | 1976-07-14 |
| NO150157B (no) | 1984-05-21 |
| IT1054782B (it) | 1981-11-30 |
| ATA17476A (de) | 1980-10-15 |
| PT64691B (fr) | 1977-08-09 |
| CH627464A5 (en) | 1982-01-15 |
| JPS5195085A (en) | 1976-08-20 |
| ES444144A1 (es) | 1977-08-16 |
| NO811390L (no) | 1976-07-15 |
| CS190550B2 (en) | 1979-05-31 |
| NO149387C (no) | 1984-04-11 |
| CS190509B2 (en) | 1979-05-31 |
| MX3745E (es) | 1981-06-11 |
| DK12376A (da) | 1976-07-15 |
| AT362376B (de) | 1981-05-11 |
| FI760052A7 (enrdf_load_html_response) | 1976-07-15 |
| NO149387B (no) | 1984-01-02 |
| BE837561A (fr) | 1976-07-14 |
| LU74174A1 (enrdf_load_html_response) | 1976-12-31 |
| PT64691A (fr) | 1976-05-01 |
| NO760101L (enrdf_load_html_response) | 1976-07-15 |
| NL7600204A (nl) | 1976-07-16 |
| FR2297852A1 (fr) | 1976-08-13 |
| NO150157C (no) | 1984-08-29 |
| HU175610B (hu) | 1980-09-28 |
| SE422796B (sv) | 1982-03-29 |
| SE7600321L (sv) | 1976-07-15 |
| FR2297852B1 (enrdf_load_html_response) | 1979-08-31 |
| GB1538775A (en) | 1979-01-24 |
| IE41999B1 (en) | 1980-05-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |