CA1140138A - Method of preparation of lower alkyl 4,10- dihydro-10-oxothieno[3,2-c][1]benzoxepin-8- acetate - Google Patents
Method of preparation of lower alkyl 4,10- dihydro-10-oxothieno[3,2-c][1]benzoxepin-8- acetateInfo
- Publication number
- CA1140138A CA1140138A CA000345539A CA345539A CA1140138A CA 1140138 A CA1140138 A CA 1140138A CA 000345539 A CA000345539 A CA 000345539A CA 345539 A CA345539 A CA 345539A CA 1140138 A CA1140138 A CA 1140138A
- Authority
- CA
- Canada
- Prior art keywords
- oxothieno
- benzoxepin
- dihydro
- acetate
- lower alkyl
- 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
- 238000000034 method Methods 0.000 title claims abstract description 21
- -1 alkyl 4,10- dihydro-10-oxothieno[3,2-c][1]benzoxepin-8- acetate Chemical compound 0.000 title claims abstract description 8
- 238000002360 preparation method Methods 0.000 title abstract description 3
- 229910052782 aluminium Inorganic materials 0.000 claims abstract description 11
- ATOWXRKBPWNXOS-UHFFFAOYSA-N 3-[[4-(carboxymethyl)phenoxy]methyl]thiophene-2-carboxylic acid Chemical compound C1=CC(CC(=O)O)=CC=C1OCC1=C(C(O)=O)SC=C1 ATOWXRKBPWNXOS-UHFFFAOYSA-N 0.000 claims abstract description 3
- 150000004820 halides Chemical class 0.000 claims abstract 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 8
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical group Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical group ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 4
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 238000011065 in-situ storage Methods 0.000 claims description 2
- HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical group BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-N 0.000 claims description 2
- 230000002140 halogenating effect Effects 0.000 claims 3
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 238000007363 ring formation reaction Methods 0.000 claims 1
- 230000002194 synthesizing effect Effects 0.000 claims 1
- PUGUQINMNYINPK-UHFFFAOYSA-N tert-butyl 4-(2-chloroacetyl)piperazine-1-carboxylate Chemical group CC(C)(C)OC(=O)N1CCN(C(=O)CCl)CC1 PUGUQINMNYINPK-UHFFFAOYSA-N 0.000 claims 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 abstract description 7
- 238000006243 chemical reaction Methods 0.000 abstract description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 5
- 230000015572 biosynthetic process Effects 0.000 abstract description 5
- 230000032050 esterification Effects 0.000 abstract description 5
- 238000005886 esterification reaction Methods 0.000 abstract description 5
- 238000002955 isolation Methods 0.000 abstract description 3
- 239000013067 intermediate product Substances 0.000 abstract description 2
- 239000002351 wastewater Substances 0.000 abstract description 2
- RWQMNIYXUUOSEB-UHFFFAOYSA-N 2-(10-oxo-4h-thieno[3,2-c][1]benzoxepin-8-yl)acetic acid Chemical compound O=C1C2=CC(CC(=O)O)=CC=C2OCC2=C1SC=C2 RWQMNIYXUUOSEB-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 238000003912 environmental pollution Methods 0.000 abstract 1
- 238000000746 purification Methods 0.000 abstract 1
- 238000006798 ring closing metathesis reaction Methods 0.000 abstract 1
- 235000010210 aluminium Nutrition 0.000 description 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 2
- 150000001266 acyl halides Chemical class 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 229960004592 isopropanol Drugs 0.000 description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 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 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 101100401100 Caenorhabditis elegans mes-1 gene Proteins 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241000861718 Chloris <Aves> Species 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- 229910006121 SOBr2 Inorganic materials 0.000 description 1
- 229910006124 SOCl2 Inorganic materials 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/011,943 US4211877A (en) | 1979-02-13 | 1979-02-13 | Method of preparation of isopropyl 4,10-dihydro-10-oxothieno[3,2-c][1]benzoxepin-8-acetate |
| US011,943 | 1979-02-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1140138A true CA1140138A (en) | 1983-01-25 |
Family
ID=21752631
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000345539A Expired CA1140138A (en) | 1979-02-13 | 1980-02-12 | Method of preparation of lower alkyl 4,10- dihydro-10-oxothieno[3,2-c][1]benzoxepin-8- acetate |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US4211877A (OSRAM) |
| EP (1) | EP0014478A1 (OSRAM) |
| JP (1) | JPS55133383A (OSRAM) |
| AU (1) | AU5545480A (OSRAM) |
| CA (1) | CA1140138A (OSRAM) |
| DK (1) | DK59680A (OSRAM) |
| ES (1) | ES8103091A1 (OSRAM) |
| FI (1) | FI800410A7 (OSRAM) |
| GR (1) | GR73625B (OSRAM) |
| HU (1) | HU178970B (OSRAM) |
| IL (1) | IL59363A0 (OSRAM) |
| NO (1) | NO800372L (OSRAM) |
| PT (1) | PT70820A (OSRAM) |
| ZA (1) | ZA80784B (OSRAM) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS53146799A (en) * | 1977-05-27 | 1978-12-20 | Sumitomo Chem Co Ltd | Novel epoxy resin and its preparation |
| US4496580A (en) * | 1981-07-23 | 1985-01-29 | Hoechst-Roussel Pharmaceuticals Inc. | Oxothienobenzoxepins |
| US4560701A (en) * | 1981-07-23 | 1985-12-24 | Hoechst-Roussel Pharmaceuticals Inc. | Oxothienobenzoxepins, medicinal use, and process for the preparation thereof |
| US4477465A (en) * | 1983-03-10 | 1984-10-16 | Hoechst-Roussel Pharmaceuticals Inc. | Substituted 4,10-dihydro-10-oxothieno benzoxepins |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS51136697A (en) * | 1975-05-23 | 1976-11-26 | Dai Ichi Seiyaku Co Ltd | Process for preparing thienothiepines or oxepines |
| US4025640A (en) * | 1975-08-26 | 1977-05-24 | American Hoechst Corporation | Oxothienobenzoxepin-acetic acids, precursors and derivatives thereof |
-
1979
- 1979-02-13 US US06/011,943 patent/US4211877A/en not_active Expired - Lifetime
-
1980
- 1980-02-07 ES ES488328A patent/ES8103091A1/es not_active Expired
- 1980-02-11 GR GR61184A patent/GR73625B/el unknown
- 1980-02-11 FI FI800410A patent/FI800410A7/fi not_active Application Discontinuation
- 1980-02-11 IL IL59363A patent/IL59363A0/xx unknown
- 1980-02-11 EP EP80100680A patent/EP0014478A1/de not_active Withdrawn
- 1980-02-12 AU AU55454/80A patent/AU5545480A/en not_active Abandoned
- 1980-02-12 DK DK59680A patent/DK59680A/da not_active Application Discontinuation
- 1980-02-12 NO NO800372A patent/NO800372L/no unknown
- 1980-02-12 HU HU8080309A patent/HU178970B/hu unknown
- 1980-02-12 PT PT70820A patent/PT70820A/pt unknown
- 1980-02-12 CA CA000345539A patent/CA1140138A/en not_active Expired
- 1980-02-12 ZA ZA00800784A patent/ZA80784B/xx unknown
- 1980-02-13 JP JP1559580A patent/JPS55133383A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| PT70820A (en) | 1980-03-01 |
| ZA80784B (en) | 1981-02-25 |
| FI800410A7 (fi) | 1981-01-01 |
| IL59363A0 (en) | 1980-05-30 |
| NO800372L (no) | 1980-08-14 |
| JPS55133383A (en) | 1980-10-17 |
| ES488328A0 (es) | 1981-02-16 |
| US4211877A (en) | 1980-07-08 |
| HU178970B (en) | 1982-07-28 |
| DK59680A (da) | 1980-08-14 |
| GR73625B (OSRAM) | 1984-03-26 |
| EP0014478A1 (de) | 1980-08-20 |
| AU5545480A (en) | 1980-08-21 |
| ES8103091A1 (es) | 1981-02-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |