NO762726L - Fremgangsm}te for fremstilling av 6,11-dihydrodibenzo-(b.e.)-thiepin-11-one-3-eddiksyre og nye mellomprodukter for fremstilling derav - Google Patents
Fremgangsm}te for fremstilling av 6,11-dihydrodibenzo-(b.e.)-thiepin-11-one-3-eddiksyre og nye mellomprodukter for fremstilling deravInfo
- Publication number
- NO762726L NO762726L NO762726A NO762726A NO762726L NO 762726 L NO762726 L NO 762726L NO 762726 A NO762726 A NO 762726A NO 762726 A NO762726 A NO 762726A NO 762726 L NO762726 L NO 762726L
- Authority
- NO
- Norway
- Prior art keywords
- dihydrodibenzo
- thiepin
- acetic acid
- reagent
- sodium salt
- Prior art date
Links
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 title claims description 10
- 238000000034 method Methods 0.000 title claims description 10
- 238000002360 preparation method Methods 0.000 title description 4
- 239000013067 intermediate product Substances 0.000 title 1
- 239000003153 chemical reaction reagent Substances 0.000 claims description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims description 5
- KDAOIQISGNNKRB-UHFFFAOYSA-N [Na].CCOP(=O)(OCC)C(N(C)C)P(=O)(OCC)OCC Chemical compound [Na].CCOP(=O)(OCC)C(N(C)C)P(=O)(OCC)OCC KDAOIQISGNNKRB-UHFFFAOYSA-N 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims 1
- XQRLCLUYWUNEEH-UHFFFAOYSA-L diphosphonate(2-) Chemical compound [O-]P(=O)OP([O-])=O XQRLCLUYWUNEEH-UHFFFAOYSA-L 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 159000000000 sodium salts Chemical class 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- -1 diphosphonate alkali metal salt Chemical class 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 238000004809 thin layer chromatography Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 238000002955 isolation Methods 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- SQDDGOVNJMIFFT-UHFFFAOYSA-N 1,1-bis(diethoxyphosphoryl)-n,n-dimethylmethanamine Chemical compound CCOP(=O)(OCC)C(N(C)C)P(=O)(OCC)OCC SQDDGOVNJMIFFT-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229940093499 ethyl acetate Drugs 0.000 description 2
- 235000019439 ethyl acetate Nutrition 0.000 description 2
- 239000002024 ethyl acetate extract Substances 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- JZUFKLXOESDKRF-UHFFFAOYSA-N Chlorothiazide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NCNS2(=O)=O JZUFKLXOESDKRF-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- FCNFFFJEKHPYJF-UHFFFAOYSA-N [Na].CCCN(CCC)C(P(=O)(OCC)OCC)P(=O)(OCC)OCC Chemical compound [Na].CCCN(CCC)C(P(=O)(OCC)OCC)P(=O)(OCC)OCC FCNFFFJEKHPYJF-UHFFFAOYSA-N 0.000 description 1
- YKRJGQKAPCNBSA-UHFFFAOYSA-N [Na].CCN(CC)C(P(=O)(OC)OC)P(=O)(OC)OC Chemical compound [Na].CCN(CC)C(P(=O)(OC)OC)P(=O)(OC)OC YKRJGQKAPCNBSA-UHFFFAOYSA-N 0.000 description 1
- BLTBFMAJTGQSAQ-UHFFFAOYSA-N [Na].CCOP(=O)(OCC)C(N(CC)CC)P(=O)(OCC)OCC Chemical compound [Na].CCOP(=O)(OCC)C(N(CC)CC)P(=O)(OCC)OCC BLTBFMAJTGQSAQ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000004821 distillation Methods 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
- 238000001914 filtration Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- SIAPCJWMELPYOE-UHFFFAOYSA-N lithium hydride Chemical compound [LiH] SIAPCJWMELPYOE-UHFFFAOYSA-N 0.000 description 1
- 229910000103 lithium hydride Inorganic materials 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having sulfur atoms, with or without selenium or tellurium atoms, as the only ring hetero atoms
- C07F9/655381—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having sulfur atoms, with or without selenium or tellurium atoms, as the only ring hetero atoms the sulfur atom being part of a seven-(or more) membered ring
- C07F9/65539—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having sulfur atoms, with or without selenium or tellurium atoms, as the only ring hetero atoms the sulfur atom being part of a seven-(or more) membered ring condensed with carbocyclic rings or carbocyclic ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D337/00—Heterocyclic compounds containing rings of more than six members having one sulfur atom as the only ring hetero atom
- C07D337/02—Seven-membered rings
- C07D337/06—Seven-membered rings condensed with carbocyclic rings or ring systems
- C07D337/10—Seven-membered rings condensed with carbocyclic rings or ring systems condensed with two six-membered rings
- C07D337/12—[b,e]-condensed
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/697,652 US4051150A (en) | 1976-06-18 | 1976-06-18 | 3-(2-Dialkylamino-2-dialkylphosphonylvinyl)-6,11-dihydrodibenzo-[b.e.]-thiepin-11-one |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO762726L true NO762726L (no) | 1977-12-20 |
Family
ID=24801965
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO762726A NO762726L (no) | 1976-06-18 | 1976-08-05 | Fremgangsm}te for fremstilling av 6,11-dihydrodibenzo-(b.e.)-thiepin-11-one-3-eddiksyre og nye mellomprodukter for fremstilling derav |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4051150A (cs) |
| DK (1) | DK351476A (cs) |
| ES (1) | ES459899A1 (cs) |
| FI (1) | FI762238A7 (cs) |
| NO (1) | NO762726L (cs) |
| SE (1) | SE7608722L (cs) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4130654A (en) * | 1978-01-30 | 1978-12-19 | Syntex (U.S.A.) Inc. | Novel 4-(8X-6,11-dihydrodibenzo-[b.e.]-thiepin-11-one-3-yl)-4-oxobutyric acids, methods of preparation, compositions and uses thereof |
-
1976
- 1976-06-18 US US05/697,652 patent/US4051150A/en not_active Expired - Lifetime
- 1976-08-03 SE SE7608722A patent/SE7608722L/xx unknown
- 1976-08-04 FI FI762238A patent/FI762238A7/fi not_active Application Discontinuation
- 1976-08-04 DK DK351476A patent/DK351476A/da unknown
- 1976-08-05 NO NO762726A patent/NO762726L/no unknown
-
1977
- 1977-06-17 ES ES459899A patent/ES459899A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| US4051150A (en) | 1977-09-27 |
| ES459899A1 (es) | 1978-11-16 |
| DK351476A (da) | 1977-12-19 |
| SE7608722L (sv) | 1977-12-19 |
| FI762238A7 (cs) | 1977-12-19 |
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