CH623049A5 - Process for the preparation of 2,3-dichloro-4-(2-thenoyl)phenoxyacetic acid - Google Patents
Process for the preparation of 2,3-dichloro-4-(2-thenoyl)phenoxyacetic acid Download PDFInfo
- Publication number
- CH623049A5 CH623049A5 CH1151077A CH1151077A CH623049A5 CH 623049 A5 CH623049 A5 CH 623049A5 CH 1151077 A CH1151077 A CH 1151077A CH 1151077 A CH1151077 A CH 1151077A CH 623049 A5 CH623049 A5 CH 623049A5
- Authority
- CH
- Switzerland
- Prior art keywords
- dichloro
- thenoyl
- thienyl
- ketone
- ch2oh
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 11
- AGHANLSBXUWXTB-UHFFFAOYSA-N tienilic acid Chemical compound ClC1=C(Cl)C(OCC(=O)O)=CC=C1C(=O)C1=CC=CS1 AGHANLSBXUWXTB-UHFFFAOYSA-N 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims description 3
- 239000000203 mixture Substances 0.000 claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 8
- 239000007800 oxidant agent Substances 0.000 claims description 6
- 239000012286 potassium permanganate Substances 0.000 claims description 6
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 5
- 239000011707 mineral Substances 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 4
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 claims 2
- QLOKJRIVRGCVIM-UHFFFAOYSA-N 1-[(4-methylsulfanylphenyl)methyl]piperazine Chemical compound C1=CC(SC)=CC=C1CN1CCNCC1 QLOKJRIVRGCVIM-UHFFFAOYSA-N 0.000 claims 1
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000000155 melt Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- PPDIALCNVFLTST-UHFFFAOYSA-N (2,3-dichloro-4-hydroxyphenyl)-thiophen-2-ylmethanone Chemical compound ClC1=C(Cl)C(O)=CC=C1C(=O)C1=CC=CS1 PPDIALCNVFLTST-UHFFFAOYSA-N 0.000 description 5
- 239000012467 final product Substances 0.000 description 5
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 4
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- ZEDCNXAUVXXFGO-UHFFFAOYSA-N [2,3-dichloro-4-(2,3-dihydroxypropoxy)phenyl]-thiophen-2-ylmethanone Chemical compound ClC1=C(Cl)C(OCC(O)CO)=CC=C1C(=O)C1=CC=CS1 ZEDCNXAUVXXFGO-UHFFFAOYSA-N 0.000 description 3
- SGOYQCSJAAOKIQ-UHFFFAOYSA-N [2,3-dichloro-4-(2-hydroxyethoxy)phenyl]-thiophen-2-ylmethanone Chemical compound ClC1=C(Cl)C(OCCO)=CC=C1C(=O)C1=CC=CS1 SGOYQCSJAAOKIQ-UHFFFAOYSA-N 0.000 description 3
- -1 dichloro-4- (2-thenoyl) phenoxyacetaldehyde Chemical compound 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- SSZWWUDQMAHNAQ-UHFFFAOYSA-N 3-chloropropane-1,2-diol Chemical compound OCC(O)CCl SSZWWUDQMAHNAQ-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000012670 alkaline solution Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 235000010269 sulphur dioxide Nutrition 0.000 description 2
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 2
- 229960000356 tienilic acid Drugs 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 1
- FUSFWUFSEJXMRQ-UHFFFAOYSA-N 2-bromo-1,1-dimethoxyethane Chemical compound COC(CBr)OC FUSFWUFSEJXMRQ-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- 229940116731 Uricosuric agent Drugs 0.000 description 1
- CYDNYMJAQROEGB-UHFFFAOYSA-N [2,3-dichloro-4-(2,2-dimethoxyethoxy)phenyl]-thiophen-2-ylmethanone Chemical compound ClC1=C(Cl)C(OCC(OC)OC)=CC=C1C(=O)C1=CC=CS1 CYDNYMJAQROEGB-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- GUTQMBQKTSGBPQ-UHFFFAOYSA-N dithiophen-2-ylmethanone Chemical compound C=1C=CSC=1C(=O)C1=CC=CS1 GUTQMBQKTSGBPQ-UHFFFAOYSA-N 0.000 description 1
- 239000002934 diuretic Substances 0.000 description 1
- 230000001882 diuretic effect Effects 0.000 description 1
- DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 239000003383 uricosuric agent Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/22—Radicals substituted by doubly bound hetero atoms, or by two hetero atoms other than halogen singly bound to the same carbon atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/10—Antioedematous agents; Diuretics
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Diabetes (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Hematology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Steroid Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7628273A FR2364915A1 (fr) | 1976-09-21 | 1976-09-21 | Nouveau procede de preparation de l'acide dichloro-2,3 (thenoyl-2)-4 phenoxyacetique |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH623049A5 true CH623049A5 (en) | 1981-05-15 |
Family
ID=9177880
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1151077A CH623049A5 (en) | 1976-09-21 | 1977-09-20 | Process for the preparation of 2,3-dichloro-4-(2-thenoyl)phenoxyacetic acid |
Country Status (11)
| Country | Link |
|---|---|
| JP (1) | JPS5340757A (enExample) |
| CA (1) | CA1083161A (enExample) |
| CH (1) | CH623049A5 (enExample) |
| ES (1) | ES462471A1 (enExample) |
| FR (1) | FR2364915A1 (enExample) |
| GR (1) | GR63644B (enExample) |
| HU (1) | HU173515B (enExample) |
| IL (1) | IL52880A (enExample) |
| IT (1) | IT1086082B (enExample) |
| PL (1) | PL200935A1 (enExample) |
| PT (1) | PT67034B (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4166061A (en) * | 1977-11-02 | 1979-08-28 | Smithkline Corporation | Use of cyclic esters to prepare 2,3-dichloro-4-(2-thenoyl)phenoxyacetic acid |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1084135A (enExample) * | 1963-12-03 | |||
| US3379755A (en) * | 1964-06-04 | 1968-04-23 | Merck & Co Inc | Preparation of (4-alkanoylphenoxy) acetic acids by oxidation |
-
1976
- 1976-09-21 FR FR7628273A patent/FR2364915A1/fr active Granted
-
1977
- 1977-09-01 CA CA286,002A patent/CA1083161A/en not_active Expired
- 1977-09-02 IL IL52880A patent/IL52880A/xx unknown
- 1977-09-07 IT IT27348/77A patent/IT1086082B/it active
- 1977-09-15 PT PT67034A patent/PT67034B/pt unknown
- 1977-09-19 PL PL20093577A patent/PL200935A1/xx unknown
- 1977-09-19 GR GR54373A patent/GR63644B/el unknown
- 1977-09-20 JP JP11389977A patent/JPS5340757A/ja active Pending
- 1977-09-20 CH CH1151077A patent/CH623049A5/fr not_active IP Right Cessation
- 1977-09-20 HU HU77RO944A patent/HU173515B/hu unknown
- 1977-09-20 ES ES462471A patent/ES462471A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GR63644B (en) | 1979-11-28 |
| FR2364915B1 (enExample) | 1982-02-12 |
| PT67034B (en) | 1979-02-15 |
| CA1083161A (en) | 1980-08-05 |
| HU173515B (hu) | 1979-05-28 |
| JPS5340757A (en) | 1978-04-13 |
| PL200935A1 (pl) | 1978-05-22 |
| PT67034A (en) | 1977-10-01 |
| IT1086082B (it) | 1985-05-28 |
| ES462471A1 (es) | 1978-07-16 |
| IL52880A (en) | 1981-11-30 |
| IL52880A0 (en) | 1977-11-30 |
| FR2364915A1 (fr) | 1978-04-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |