CH627464A5 - Process for the preparation of 6,11-dihydro-11-oxodibenz[b,e]oxepinealkanoic acids - Google Patents
Process for the preparation of 6,11-dihydro-11-oxodibenz[b,e]oxepinealkanoic acids Download PDFInfo
- Publication number
- CH627464A5 CH627464A5 CH33876A CH33876A CH627464A5 CH 627464 A5 CH627464 A5 CH 627464A5 CH 33876 A CH33876 A CH 33876A CH 33876 A CH33876 A CH 33876A CH 627464 A5 CH627464 A5 CH 627464A5
- Authority
- CH
- Switzerland
- Prior art keywords
- formula
- chloride
- halide
- iron
- group
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 43
- 239000002253 acid Substances 0.000 title claims description 24
- 150000007513 acids Chemical class 0.000 title claims description 14
- 238000002360 preparation method Methods 0.000 title claims description 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 24
- -1 dicarboxylic acid halide Chemical class 0.000 claims description 18
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 16
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 11
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 8
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 7
- 239000002841 Lewis acid Substances 0.000 claims description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
- 239000000460 chlorine Substances 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 claims description 7
- 150000007517 lewis acids Chemical class 0.000 claims description 7
- 239000011541 reaction mixture Substances 0.000 claims description 7
- 238000007363 ring formation reaction Methods 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 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
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 229910052731 fluorine Chemical group 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- ATYBXHSAIOKLMG-UHFFFAOYSA-N oxepin Chemical compound O1C=CC=CC=C1 ATYBXHSAIOKLMG-UHFFFAOYSA-N 0.000 claims description 4
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 238000006116 polymerization reaction Methods 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 5
- 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 claims 5
- 229910052799 carbon Inorganic materials 0.000 claims 4
- 150000001721 carbon Chemical group 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 3
- 239000011737 fluorine Chemical group 0.000 claims 3
- MSABOFMROKLSRD-UHFFFAOYSA-N [Fe].S(=O)(Cl)Cl Chemical compound [Fe].S(=O)(Cl)Cl MSABOFMROKLSRD-UHFFFAOYSA-N 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 150000002500 ions Chemical class 0.000 claims 1
- 230000002035 prolonged effect Effects 0.000 claims 1
- 238000007086 side reaction Methods 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 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 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 235000011121 sodium hydroxide Nutrition 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 239000011968 lewis acid catalyst Substances 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 150000001991 dicarboxylic acids Chemical class 0.000 description 3
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 3
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000004809 thin layer chromatography Methods 0.000 description 3
- XINSTAFRTHLGEX-UHFFFAOYSA-N 2-(1-oxo-2H-benzo[c][1]benzoxepin-2-yl)acetic acid Chemical compound O=C1C(C=CC=2OC=C3C(=CC21)C=CC=C3)CC(=O)O XINSTAFRTHLGEX-UHFFFAOYSA-N 0.000 description 2
- WRBIGFABHMMVLJ-UHFFFAOYSA-N 2-(1-oxo-6,11-dihydro-2h-benzo[c][1]benzoxepin-2-yl)acetic acid Chemical compound C1C2=CC=CC=C2COC2=C1C(=O)C(CC(=O)O)C=C2 WRBIGFABHMMVLJ-UHFFFAOYSA-N 0.000 description 2
- MIMZGFBPGISKHQ-UHFFFAOYSA-N 2-(oxepin-3-yl)acetic acid Chemical compound OC(=O)CC1=COC=CC=C1 MIMZGFBPGISKHQ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 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
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- 230000002140 halogenating effect Effects 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- BTEWWBNTAGZPIU-UHFFFAOYSA-N 2-(11-oxo-6h-benzo[c][1]benzoxepin-1-yl)acetic acid Chemical compound O1CC2=CC=CC=C2C(=O)C2=C1C=CC=C2CC(=O)O BTEWWBNTAGZPIU-UHFFFAOYSA-N 0.000 description 1
- NVQMOCHYIMJQIC-UHFFFAOYSA-N 2-[[3-(carboxymethyl)phenoxy]methyl]benzoic acid Chemical compound OC(=O)CC1=CC=CC(OCC=2C(=CC=CC=2)C(O)=O)=C1 NVQMOCHYIMJQIC-UHFFFAOYSA-N 0.000 description 1
- LTEOHQLUJPPHMP-UHFFFAOYSA-N C(C)O.[P] Chemical compound C(C)O.[P] LTEOHQLUJPPHMP-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical group ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- 238000010917 Friedel-Crafts cyclization Methods 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- 230000001760 anti-analgesic effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000003402 intramolecular cyclocondensation reaction Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229960003424 phenylacetic acid Drugs 0.000 description 1
- 239000003279 phenylacetic acid Substances 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000012265 solid product Substances 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 |
|---|---|
| CH627464A5 true CH627464A5 (en) | 1982-01-15 |
Family
ID=24157637
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH33876A CH627464A5 (en) | 1975-01-14 | 1976-01-13 | Process for the preparation of 6,11-dihydro-11-oxodibenz[b,e]oxepinealkanoic acids |
Country Status (20)
| Country | Link |
|---|---|
| JP (1) | JPS5195085A (cs) |
| AT (1) | AT362376B (cs) |
| BE (1) | BE837561A (cs) |
| CA (1) | CA1081240A (cs) |
| CH (1) | CH627464A5 (cs) |
| CS (2) | CS190550B2 (cs) |
| DK (1) | DK12376A (cs) |
| ES (1) | ES444144A1 (cs) |
| FI (1) | FI760052A7 (cs) |
| FR (1) | FR2297852A1 (cs) |
| GB (1) | GB1538775A (cs) |
| HU (1) | HU175610B (cs) |
| IE (1) | IE41999B1 (cs) |
| IT (1) | IT1054782B (cs) |
| LU (1) | LU74174A1 (cs) |
| MX (1) | MX3745E (cs) |
| NL (1) | NL7600204A (cs) |
| NO (2) | NO149387C (cs) |
| PT (1) | PT64691B (cs) |
| SE (1) | SE422796B (cs) |
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 |
| JP2005521721A (ja) | 2002-03-27 | 2005-07-21 | スミスクライン・ビーチャム・コーポレイション | 酸およびエステル化合物ならびにその使用方法 |
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 IT IT19179/76A patent/IT1054782B/it active
- 1976-01-12 FI FI760052A patent/FI760052A7/fi not_active Application Discontinuation
- 1976-01-13 CH CH33876A patent/CH627464A5/de not_active IP Right Cessation
- 1976-01-13 CS CS777409A patent/CS190550B2/cs unknown
- 1976-01-13 LU LU74174A patent/LU74174A1/xx unknown
- 1976-01-13 CS CS76222A patent/CS190509B2/cs unknown
- 1976-01-13 PT PT64691A patent/PT64691B/pt unknown
- 1976-01-13 NO NO760101A patent/NO149387C/no unknown
- 1976-01-13 DK DK12376*#A patent/DK12376A/da not_active Application Discontinuation
- 1976-01-13 GB GB1181/76A patent/GB1538775A/en not_active Expired
- 1976-01-13 IE IE54/76A patent/IE41999B1/en unknown
- 1976-01-13 CA CA243,400A patent/CA1081240A/en not_active Expired
- 1976-01-13 HU HU76HO1871A patent/HU175610B/hu unknown
- 1976-01-13 AT AT17476A patent/AT362376B/de not_active IP Right Cessation
- 1976-01-14 JP JP51003719A patent/JPS5195085A/ja active Pending
- 1976-01-14 FR FR7600784A patent/FR2297852A1/fr active Granted
- 1976-01-14 MX MX762392U patent/MX3745E/es unknown
- 1976-01-14 SE SE7600321A patent/SE422796B/xx unknown
- 1976-01-14 BE BE163509A patent/BE837561A/xx not_active IP Right Cessation
-
1981
- 1981-04-24 NO NO811390A patent/NO150157C/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NO149387C (no) | 1984-04-11 |
| NO150157B (no) | 1984-05-21 |
| JPS5195085A (en) | 1976-08-20 |
| MX3745E (es) | 1981-06-11 |
| PT64691A (fr) | 1976-05-01 |
| DK12376A (da) | 1976-07-15 |
| IT1054782B (it) | 1981-11-30 |
| PT64691B (fr) | 1977-08-09 |
| SE7600321L (sv) | 1976-07-15 |
| NO811390L (no) | 1976-07-15 |
| NO150157C (no) | 1984-08-29 |
| NO149387B (no) | 1984-01-02 |
| NL7600204A (nl) | 1976-07-16 |
| ATA17476A (de) | 1980-10-15 |
| FI760052A7 (cs) | 1976-07-15 |
| CS190509B2 (en) | 1979-05-31 |
| IE41999L (en) | 1976-07-14 |
| SE422796B (sv) | 1982-03-29 |
| GB1538775A (en) | 1979-01-24 |
| LU74174A1 (cs) | 1976-12-31 |
| FR2297852A1 (fr) | 1976-08-13 |
| BE837561A (fr) | 1976-07-14 |
| AT362376B (de) | 1981-05-11 |
| CA1081240A (en) | 1980-07-08 |
| IE41999B1 (en) | 1980-05-07 |
| HU175610B (hu) | 1980-09-28 |
| NO760101L (cs) | 1976-07-15 |
| CS190550B2 (en) | 1979-05-31 |
| FR2297852B1 (cs) | 1979-08-31 |
| ES444144A1 (es) | 1977-08-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |