CA1089475A - 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 acidInfo
- Publication number
- CA1089475A CA1089475A CA286,001A CA286001A CA1089475A CA 1089475 A CA1089475 A CA 1089475A CA 286001 A CA286001 A CA 286001A CA 1089475 A CA1089475 A CA 1089475A
- Authority
- CA
- Canada
- Prior art keywords
- fact
- dichloro
- diacid
- formula
- process according
- 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 14
- 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 abstract description 8
- 238000002360 preparation method Methods 0.000 title claims description 5
- 230000007062 hydrolysis Effects 0.000 claims abstract description 8
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract description 8
- 150000005690 diesters Chemical class 0.000 claims abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- 238000010438 heat treatment Methods 0.000 claims abstract description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 4
- -1 2,3-dichloro-4-hydroxyphenyl Chemical group 0.000 claims description 3
- 239000000725 suspension Substances 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical class OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 1
- 125000005907 alkyl ester group Chemical group 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 150000002576 ketones Chemical class 0.000 claims 1
- 229940116731 Uricosuric agent Drugs 0.000 abstract description 2
- 239000002934 diuretic Substances 0.000 abstract description 2
- 230000001882 diuretic effect Effects 0.000 abstract description 2
- 239000003383 uricosuric agent Substances 0.000 abstract description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000006114 decarboxylation reaction Methods 0.000 description 6
- LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical compound OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
- WEDRHXJXOOIYSD-UHFFFAOYSA-N 2-[2,3-dichloro-4-(thiophene-2-carbonyl)phenoxy]propanedioic acid Chemical compound ClC1=C(Cl)C(OC(C(=O)O)C(O)=O)=CC=C1C(=O)C1=CC=CS1 WEDRHXJXOOIYSD-UHFFFAOYSA-N 0.000 description 2
- HVQAHNBSEFQMPZ-UHFFFAOYSA-N 2-phenoxypropanedioic acid Chemical compound OC(=O)C(C(O)=O)OC1=CC=CC=C1 HVQAHNBSEFQMPZ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 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 1
- FBEHFRAORPEGFH-UHFFFAOYSA-N Allyxycarb Chemical group CNC(=O)OC1=CC(C)=C(N(CC=C)CC=C)C(C)=C1 FBEHFRAORPEGFH-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- IYXGSMUGOJNHAZ-UHFFFAOYSA-N Ethyl malonate Chemical class CCOC(=O)CC(=O)OCC IYXGSMUGOJNHAZ-UHFFFAOYSA-N 0.000 description 1
- 235000019502 Orange oil Nutrition 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- WLWCQKMQYZFTDR-UHFFFAOYSA-N diethyl 2-chloropropanedioate Chemical compound CCOC(=O)C(Cl)C(=O)OCC WLWCQKMQYZFTDR-UHFFFAOYSA-N 0.000 description 1
- 239000012153 distilled water Substances 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
- 150000002148 esters Chemical class 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 159000000011 group IA salts Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229940032007 methylethyl ketone Drugs 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 229960000356 tienilic acid Drugs 0.000 description 1
- 238000011282 treatment 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)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR76/28272 | 1976-09-21 | ||
| FR7628272A FR2364914A1 (fr) | 1976-09-21 | 1976-09-21 | Procede de preparation de l'acide dichloro-2,3 (thenoyl-2)-4 phenoxy-acetique |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1089475A true CA1089475A (en) | 1980-11-11 |
Family
ID=9177879
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA286,001A Expired CA1089475A (en) | 1976-09-21 | 1977-09-01 | Process for the preparation of 2,3-dichloro-4-(2-thenoyl) phenoxyacetic acid |
Country Status (11)
| Country | Link |
|---|---|
| JP (1) | JPS5340756A (pl) |
| CA (1) | CA1089475A (pl) |
| CH (1) | CH623048A5 (pl) |
| ES (1) | ES462470A1 (pl) |
| FR (1) | FR2364914A1 (pl) |
| GR (1) | GR63627B (pl) |
| HU (1) | HU173514B (pl) |
| IL (1) | IL52879A (pl) |
| IT (1) | IT1086081B (pl) |
| PL (1) | PL200936A1 (pl) |
| PT (1) | PT67033B (pl) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FI60005C (fi) * | 1979-11-27 | 1981-11-10 | Farmos Oy | Ett nytt foerfarande foer framstaellning av (2,3-diklor-4-(2-tienylkarbonyl)fenoxi)-aettiksyra med terapeutisk aktivitet samt (2,3-diklor-4-(2-tienylkarbonyl)fenoxi)-aettiksyraanhydrid anvaendbar som mellanprodukt i foerfarandet |
| JPH0632887B2 (ja) * | 1986-08-29 | 1994-05-02 | 株式会社日立製作所 | 面取り加工方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1793212C3 (de) * | 1967-08-31 | 1974-02-21 | Egyt Gyogyszervegyeszeti Gyar, Budapest | Verfahren zur Herstellung von 2,3-Dichlor-4-butyryl-phenoxyessigsäure |
-
1976
- 1976-09-21 FR FR7628272A patent/FR2364914A1/fr active Granted
-
1977
- 1977-09-01 CA CA286,001A patent/CA1089475A/en not_active Expired
- 1977-09-02 IL IL52879A patent/IL52879A/xx unknown
- 1977-09-07 IT IT27347/77A patent/IT1086081B/it active
- 1977-09-15 PT PT67033A patent/PT67033B/pt unknown
- 1977-09-19 PL PL20093677A patent/PL200936A1/pl unknown
- 1977-09-19 GR GR54372A patent/GR63627B/el unknown
- 1977-09-20 CH CH1150977A patent/CH623048A5/fr not_active IP Right Cessation
- 1977-09-20 HU HU77RO943A patent/HU173514B/hu unknown
- 1977-09-20 ES ES462470A patent/ES462470A1/es not_active Expired
- 1977-09-20 JP JP11389877A patent/JPS5340756A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| FR2364914A1 (fr) | 1978-04-14 |
| FR2364914B1 (pl) | 1980-07-25 |
| IL52879A0 (en) | 1977-11-30 |
| ES462470A1 (es) | 1978-07-16 |
| IT1086081B (it) | 1985-05-28 |
| IL52879A (en) | 1981-09-13 |
| PL200936A1 (pl) | 1978-05-22 |
| HU173514B (hu) | 1979-05-28 |
| CH623048A5 (en) | 1981-05-15 |
| PT67033B (en) | 1979-02-15 |
| PT67033A (en) | 1977-10-01 |
| GR63627B (en) | 1979-11-27 |
| JPS5340756A (en) | 1978-04-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |