CH623048A5 - 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 PDF

Info

Publication number: CH623048A5
Authority: CH; Switzerland
Prior art keywords: dichloro; thenoyl; water; ethyl; formula
Prior art date: 1976-09-21

Application number

CH1150977A

Other languages

English (en)

French (fr)

Inventor

Jacqueline Suzanne Laforest

Original Assignee

Rolland Sa A

Priority date (The priority date 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 date listed.)

1976-09-21

Filing date

1977-09-20

Publication date

1981-05-15

1977-09-20 Application filed by Rolland Sa A filed Critical Rolland Sa A

1981-05-15 Publication of CH623048A5 publication Critical patent/CH623048A5/fr

Links

238000000034 method Methods 0.000 title claims 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 7
238000002360 preparation method Methods 0.000 title claims 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 11
238000006114 decarboxylation reaction Methods 0.000 claims 7
LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical compound OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 claims 7
239000000243 solution Substances 0.000 claims 7
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 6
238000010438 heat treatment Methods 0.000 claims 6
150000005690 diesters Chemical class 0.000 claims 5
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims 4
150000002148 esters Chemical class 0.000 claims 4
230000007062 hydrolysis Effects 0.000 claims 4
238000006460 hydrolysis reaction Methods 0.000 claims 4
239000000203 mixture Substances 0.000 claims 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
125000000217 alkyl group Chemical group 0.000 claims 3
235000019441 ethanol Nutrition 0.000 claims 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
150000003839 salts Chemical class 0.000 claims 3
239000002904 solvent Substances 0.000 claims 3
239000000725 suspension Substances 0.000 claims 3
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 claims 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims 2
HVQAHNBSEFQMPZ-UHFFFAOYSA-N 2-phenoxypropanedioic acid Chemical compound OC(=O)C(C(O)=O)OC1=CC=CC=C1 HVQAHNBSEFQMPZ-UHFFFAOYSA-N 0.000 claims 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims 2
229910002092 carbon dioxide Inorganic materials 0.000 claims 2
238000006243 chemical reaction Methods 0.000 claims 2
-1 ethyl 2,3-dichloro-4-(2-thenoyl)phenoxymalonate Chemical compound 0.000 claims 2
239000007789 gas Substances 0.000 claims 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims 2
238000001556 precipitation Methods 0.000 claims 2
239000000047 product Substances 0.000 claims 2
239000011780 sodium chloride Substances 0.000 claims 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 claims 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims 1
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 claims 1
235000019502 Orange oil Nutrition 0.000 claims 1
229940116731 Uricosuric agent Drugs 0.000 claims 1
239000002253 acid Substances 0.000 claims 1
239000007864 aqueous solution Substances 0.000 claims 1
239000001569 carbon dioxide Substances 0.000 claims 1
239000003054 catalyst Substances 0.000 claims 1
150000001875 compounds Chemical class 0.000 claims 1
238000001816 cooling Methods 0.000 claims 1
229910052802 copper Inorganic materials 0.000 claims 1
239000010949 copper Substances 0.000 claims 1
238000000354 decomposition reaction Methods 0.000 claims 1
WLWCQKMQYZFTDR-UHFFFAOYSA-N diethyl 2-chloropropanedioate Chemical compound CCOC(=O)C(Cl)C(=O)OCC WLWCQKMQYZFTDR-UHFFFAOYSA-N 0.000 claims 1
239000012153 distilled water Substances 0.000 claims 1
239000002934 diuretic Substances 0.000 claims 1
230000001882 diuretic effect Effects 0.000 claims 1
238000001035 drying Methods 0.000 claims 1
238000001704 evaporation Methods 0.000 claims 1
238000001914 filtration Methods 0.000 claims 1
229910052739 hydrogen Inorganic materials 0.000 claims 1
239000001257 hydrogen Substances 0.000 claims 1
239000005457 ice water Substances 0.000 claims 1
229910052500 inorganic mineral Inorganic materials 0.000 claims 1
239000000155 melt Substances 0.000 claims 1
239000011707 mineral Substances 0.000 claims 1
230000007935 neutral effect Effects 0.000 claims 1
239000003921 oil Substances 0.000 claims 1
235000019198 oils Nutrition 0.000 claims 1
239000010502 orange oil Substances 0.000 claims 1
239000012074 organic phase Substances 0.000 claims 1
239000002244 precipitate Substances 0.000 claims 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
239000011541 reaction mixture Substances 0.000 claims 1
238000010992 reflux Methods 0.000 claims 1
239000011734 sodium Substances 0.000 claims 1
229910052708 sodium Inorganic materials 0.000 claims 1
159000000000 sodium salts Chemical class 0.000 claims 1
239000007787 solid Substances 0.000 claims 1
239000007858 starting material Substances 0.000 claims 1
238000003756 stirring Methods 0.000 claims 1
239000000126 substance Substances 0.000 claims 1
238000002560 therapeutic procedure Methods 0.000 claims 1
229960000356 tienilic acid Drugs 0.000 claims 1
238000011282 treatment Methods 0.000 claims 1
239000003383 uricosuric agent Substances 0.000 claims 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)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Heterocyclic Compounds Containing Sulfur Atoms (AREA)

CH1150977A 1976-09-21 1977-09-20 Process for the preparation of 2,3-dichloro-4-(2-thenoyl)phenoxyacetic acid CH623048A5 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
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
CH623048A5 true CH623048A5 (en)	1981-05-15

Family

ID=9177879

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1150977A CH623048A5 (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)	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)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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 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
- 1977-09-20 CH CH1150977A patent/CH623048A5/fr not_active IP Right Cessation

Also Published As

Publication number	Publication date
JPS5340756A (en)	1978-04-13
ES462470A1 (es)	1978-07-16
PL200936A1 (pl)	1978-05-22
FR2364914A1 (fr)	1978-04-14
IT1086081B (it)	1985-05-28
IL52879A (en)	1981-09-13
FR2364914B1 (pl)	1980-07-25
IL52879A0 (en)	1977-11-30
PT67033A (en)	1977-10-01
GR63627B (en)	1979-11-27
HU173514B (hu)	1979-05-28
CA1089475A (en)	1980-11-11
PT67033B (en)	1979-02-15

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Legal Events

Date	Code	Title	Description
1991-05-31	PL	Patent ceased
2024-10-31	PL	Patent ceased