CH653681A5 - Procede de preparation de derives de l'acide 2-thiophene acetique. - Google Patents

Procede de preparation de derives de l'acide 2-thiophene acetique. Download PDF

Info

Publication number: CH653681A5
Authority: CH; Switzerland
Prior art keywords: formula; product; acid; thiophene; solvent
Prior art date: 1982-12-03

Application number

CH1966/83A

Other languages

English (en)

French (fr)

Inventor

Roger Nabet

Jean-Luc Grardel

Maurice Gallois

Original Assignee

Roussel Uclaf

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.)

1982-12-03

Filing date

1983-04-12

Publication date

1986-01-15

1983-04-12 Application filed by Roussel Uclaf filed Critical Roussel Uclaf

1986-01-15 Publication of CH653681A5 publication Critical patent/CH653681A5/fr

Links

238000000034 method Methods 0.000 title claims description 29
238000002360 preparation method Methods 0.000 title claims description 10
150000005395 2-thiopheneacetic acid derivatives Chemical class 0.000 title claims 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 39
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 37
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 30
229930192474 thiophene Natural products 0.000 claims description 16
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 12
239000002904 solvent Substances 0.000 claims description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 11
239000002253 acid Substances 0.000 claims description 11
238000006243 chemical reaction Methods 0.000 claims description 9
239000012071 phase Substances 0.000 claims description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
239000008346 aqueous phase Substances 0.000 claims description 8
HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 claims description 8
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 7
SQYNKIJPMDEDEG-UHFFFAOYSA-N paraldehyde Chemical compound CC1OC(C)OC(C)O1 SQYNKIJPMDEDEG-UHFFFAOYSA-N 0.000 claims description 7
229960003868 paraldehyde Drugs 0.000 claims description 7
VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 claims description 7
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 claims description 6
238000010992 reflux Methods 0.000 claims description 6
239000000243 solution Substances 0.000 claims description 6
KTKWUKAYWFMQSO-UHFFFAOYSA-N 2-thiophen-2-ylpropanoic acid Chemical compound OC(=O)C(C)C1=CC=CS1 KTKWUKAYWFMQSO-UHFFFAOYSA-N 0.000 claims description 5
239000003054 catalyst Substances 0.000 claims description 5
238000006276 transfer reaction Methods 0.000 claims description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
239000003444 phase transfer catalyst Substances 0.000 claims description 4
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 3
GEDJSTBRFXDCAM-UHFFFAOYSA-N 2-(1-chloroethyl)thiophene Chemical compound CC(Cl)C1=CC=CS1 GEDJSTBRFXDCAM-UHFFFAOYSA-N 0.000 claims description 3
239000003153 chemical reaction reagent Substances 0.000 claims description 3
238000000605 extraction Methods 0.000 claims description 3
JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 claims description 3
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 2
239000007864 aqueous solution Substances 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
ZXUCBXRTRRIBSO-UHFFFAOYSA-L tetrabutylazanium;sulfate Chemical compound [O-]S([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC.CCCC[N+](CCCC)(CCCC)CCCC ZXUCBXRTRRIBSO-UHFFFAOYSA-L 0.000 claims description 2
BGQMOFGZRJUORO-UHFFFAOYSA-M tetrapropylammonium bromide Chemical compound [Br-].CCC[N+](CCC)(CCC)CCC BGQMOFGZRJUORO-UHFFFAOYSA-M 0.000 claims description 2
239000000047 product Substances 0.000 claims 45
150000001299 aldehydes Chemical class 0.000 claims 10
-1 alkyl radical Chemical class 0.000 claims 9
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 6
125000005843 halogen group Chemical group 0.000 claims 6
125000004432 carbon atom Chemical group C* 0.000 claims 5
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 4
230000007062 hydrolysis Effects 0.000 claims 4
238000006460 hydrolysis reaction Methods 0.000 claims 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-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
229910052783 alkali metal Inorganic materials 0.000 claims 3
150000001340 alkali metals Chemical group 0.000 claims 3
229910052784 alkaline earth metal Inorganic materials 0.000 claims 3
239000002585 base Substances 0.000 claims 3
239000003795 chemical substances by application Substances 0.000 claims 3
239000003960 organic solvent Substances 0.000 claims 3
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 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 claims 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 2
125000000217 alkyl group Chemical group 0.000 claims 2
229910000147 aluminium phosphate Inorganic materials 0.000 claims 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
239000007810 chemical reaction solvent Substances 0.000 claims 2
239000000460 chlorine Substances 0.000 claims 2
229910052736 halogen Inorganic materials 0.000 claims 2
LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims 2
229910052700 potassium Inorganic materials 0.000 claims 2
239000011591 potassium Substances 0.000 claims 2
150000003839 salts Chemical class 0.000 claims 2
229910052708 sodium Inorganic materials 0.000 claims 2
239000011734 sodium Substances 0.000 claims 2
125000001424 substituent group Chemical group 0.000 claims 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims 2
150000003577 thiophenes Chemical class 0.000 claims 2
NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims 1
XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 claims 1
OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 claims 1
QTOABKRIUPTTPQ-UHFFFAOYSA-N 2-thiophen-2-ylpropanenitrile Chemical compound N#CC(C)C1=CC=CS1 QTOABKRIUPTTPQ-UHFFFAOYSA-N 0.000 claims 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 claims 1
239000004215 Carbon black (E152) Substances 0.000 claims 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims 1
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims 1
241001331845 Equus asinus x caballus Species 0.000 claims 1
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
239000002841 Lewis acid Substances 0.000 claims 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims 1
239000004721 Polyphenylene oxide Substances 0.000 claims 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims 1
230000001476 alcoholic effect Effects 0.000 claims 1
239000003513 alkali Substances 0.000 claims 1
150000008044 alkali metal hydroxides Chemical class 0.000 claims 1
150000001342 alkaline earth metals Chemical class 0.000 claims 1
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical class Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims 1
BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 claims 1
229910052921 ammonium sulfate Inorganic materials 0.000 claims 1
235000011130 ammonium sulphate Nutrition 0.000 claims 1
229940121363 anti-inflammatory agent Drugs 0.000 claims 1
239000002260 anti-inflammatory agent Substances 0.000 claims 1
125000004429 atom Chemical group 0.000 claims 1
230000015572 biosynthetic process Effects 0.000 claims 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
229910052794 bromium Inorganic materials 0.000 claims 1
244000309464 bull Species 0.000 claims 1
ZQULWKDLLXZZSP-UHFFFAOYSA-N calcium cyanide Chemical class [Ca+2].N#[C-].N#[C-] ZQULWKDLLXZZSP-UHFFFAOYSA-N 0.000 claims 1
229910052801 chlorine Inorganic materials 0.000 claims 1
238000003459 chloroalkylation reaction Methods 0.000 claims 1
150000003983 crown ethers Chemical class 0.000 claims 1
235000014113 dietary fatty acids Nutrition 0.000 claims 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
239000000194 fatty acid Substances 0.000 claims 1
229930195729 fatty acid Natural products 0.000 claims 1
150000004665 fatty acids Chemical class 0.000 claims 1
229910052731 fluorine Inorganic materials 0.000 claims 1
239000011737 fluorine Substances 0.000 claims 1
150000002367 halogens Chemical class 0.000 claims 1
229930195733 hydrocarbon Natural products 0.000 claims 1
150000002430 hydrocarbons Chemical class 0.000 claims 1
239000001257 hydrogen Substances 0.000 claims 1
229910052500 inorganic mineral Inorganic materials 0.000 claims 1
239000013067 intermediate product Substances 0.000 claims 1
239000011630 iodine Substances 0.000 claims 1
229910052740 iodine Inorganic materials 0.000 claims 1
239000003456 ion exchange resin Substances 0.000 claims 1
229920003303 ion-exchange polymer Polymers 0.000 claims 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
150000007517 lewis acids Chemical class 0.000 claims 1
229910052744 lithium Inorganic materials 0.000 claims 1
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical group [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
239000011707 mineral Substances 0.000 claims 1
150000002825 nitriles Chemical class 0.000 claims 1
230000020477 pH reduction Effects 0.000 claims 1
239000000825 pharmaceutical preparation Substances 0.000 claims 1
229940127557 pharmaceutical product Drugs 0.000 claims 1
239000002798 polar solvent Substances 0.000 claims 1
229920000570 polyether Polymers 0.000 claims 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
230000035484 reaction time Effects 0.000 claims 1
239000012266 salt solution Substances 0.000 claims 1
MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 claims 1
239000011877 solvent mixture Substances 0.000 claims 1
239000004094 surface-active agent Substances 0.000 claims 1
238000003786 synthesis reaction Methods 0.000 claims 1
125000005207 tetraalkylammonium group Chemical group 0.000 claims 1
NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 claims 1
TVVPMLFGPYQGTG-UHFFFAOYSA-M tetramethylphosphanium;iodide Chemical compound [I-].C[P+](C)(C)C TVVPMLFGPYQGTG-UHFFFAOYSA-M 0.000 claims 1
OSBSFAARYOCBHB-UHFFFAOYSA-N tetrapropylammonium Chemical group CCC[N+](CCC)(CCC)CCC OSBSFAARYOCBHB-UHFFFAOYSA-N 0.000 claims 1
230000007704 transition Effects 0.000 claims 1
239000013638 trimer Substances 0.000 claims 1
229910052725 zinc Inorganic materials 0.000 claims 1
239000011701 zinc Substances 0.000 claims 1
239000000203 mixture Substances 0.000 description 10
239000012074 organic phase Substances 0.000 description 8
229940015849 thiophene Drugs 0.000 description 8
238000003756 stirring Methods 0.000 description 4
239000005457 ice water Substances 0.000 description 3
239000007789 gas Substances 0.000 description 1
229920006395 saturated elastomer Polymers 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
- C07D333/12—Radicals substituted by halogen atoms or nitro or nitroso radicals
- 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
- C07D333/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Plural Heterocyclic Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Catalysts (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CH1966/83A 1982-12-03 1983-04-12 Procede de preparation de derives de l'acide 2-thiophene acetique. CH653681A5 (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FR8220272A FR2537138A1 (fr)	1982-12-03	1982-12-03	Procede de preparation de derives de l'acide 2-thiophene acetique

Publications (1)

Publication Number	Publication Date
CH653681A5 true CH653681A5 (fr)	1986-01-15

Family

ID=9279758

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1966/83A CH653681A5 (fr)	1982-12-03	1983-04-12	Procede de preparation de derives de l'acide 2-thiophene acetique.

Country Status (22)

Country	Link
JP (1)	JPS59106483A (de)
KR (1)	KR900003281B1 (de)
AT (1)	AT392785B (de)
AU (1)	AU557065B2 (de)
BE (1)	BE896440A (de)
CA (1)	CA1201442A (de)
CH (1)	CH653681A5 (de)
DE (1)	DE3314028C2 (de)
DK (1)	DK157492C (de)
ES (1)	ES521231A0 (de)
FI (1)	FI80882C (de)
FR (1)	FR2537138A1 (de)
GB (1)	GB2132608B (de)
HU (1)	HU191831B (de)
IE (1)	IE55097B1 (de)
IT (1)	IT1174758B (de)
LU (1)	LU84749A1 (de)
NL (1)	NL8301693A (de)
NZ (1)	NZ204510A (de)
PT (1)	PT76535B (de)
SE (1)	SE453918B (de)
ZA (1)	ZA832697B (de)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IT1276738B1 (it) *	1995-06-16	1997-11-03	Erregierre Spa	Processo per la preparazione di derivati dell'acido -metil-2- tiofeneacetico

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IE33054B1 (en) *	1968-04-16	1974-03-06	Ici Ltd	Heterocyclic compounds
GB2003570B (en) *	1977-06-08	1982-01-20	Imi Opella Ltd	Stop valve

1982
- 1982-12-03 FR FR8220272A patent/FR2537138A1/fr active Granted
1983
- 1983-03-28 DK DK140083A patent/DK157492C/da not_active IP Right Cessation
- 1983-03-30 SE SE8301786A patent/SE453918B/sv not_active IP Right Cessation
- 1983-03-31 FI FI831116A patent/FI80882C/fi not_active IP Right Cessation
- 1983-04-05 ES ES521231A patent/ES521231A0/es active Granted
- 1983-04-11 PT PT76535A patent/PT76535B/pt not_active IP Right Cessation
- 1983-04-12 CH CH1966/83A patent/CH653681A5/fr not_active IP Right Cessation
- 1983-04-12 BE BE0/210537A patent/BE896440A/fr unknown
- 1983-04-14 HU HU831307A patent/HU191831B/hu unknown
- 1983-04-14 LU LU84749A patent/LU84749A1/fr unknown
- 1983-04-15 AU AU13573/83A patent/AU557065B2/en not_active Ceased
- 1983-04-18 ZA ZA832697A patent/ZA832697B/xx unknown
- 1983-04-18 DE DE3314028A patent/DE3314028C2/de not_active Expired - Lifetime
- 1983-04-23 KR KR1019830001730A patent/KR900003281B1/ko not_active Expired
- 1983-05-04 IT IT48216/83A patent/IT1174758B/it active Protection Beyond IP Right Term
- 1983-05-09 GB GB08312702A patent/GB2132608B/en not_active Expired
- 1983-05-10 IE IE1074/83A patent/IE55097B1/en not_active IP Right Cessation
- 1983-05-11 NL NL8301693A patent/NL8301693A/nl active Search and Examination
- 1983-05-20 JP JP58087836A patent/JPS59106483A/ja active Granted
- 1983-06-09 NZ NZ204510A patent/NZ204510A/en unknown
- 1983-07-28 CA CA000433422A patent/CA1201442A/fr not_active Expired
- 1983-08-08 AT AT2867/83A patent/AT392785B/de not_active IP Right Cessation

Also Published As

Publication number	Publication date
CA1201442A (fr)	1986-03-04
IE831074L (en)	1984-06-03
KR840006987A (ko)	1984-12-04
SE8301786L (sv)	1984-06-04
GB8312702D0 (en)	1983-06-15
LU84749A1 (fr)	1983-12-05
AT392785B (de)	1991-06-10
DE3314028A1 (de)	1984-06-07
PT76535B (fr)	1986-03-12
ES8401958A1 (es)	1984-01-01
ES521231A0 (es)	1984-01-01
HU191831B (en)	1987-04-28
AU557065B2 (en)	1986-12-04
PT76535A (fr)	1983-05-01
FI80882B (fi)	1990-04-30
NZ204510A (en)	1986-02-21
KR900003281B1 (ko)	1990-05-12
FR2537138A1 (fr)	1984-06-08
DK140083D0 (da)	1983-03-28
FI80882C (fi)	1990-08-10
FI831116L (fi)	1984-06-04
SE453918B (sv)	1988-03-14
NL8301693A (nl)	1984-07-02
FR2537138B1 (de)	1985-05-24
BE896440A (fr)	1983-10-12
IE55097B1 (en)	1990-05-23
DE3314028C2 (de)	1995-05-24
ATA286783A (de)	1990-11-15
DK157492C (da)	1990-06-11
AU1357383A (en)	1984-06-07
IT8348216A0 (it)	1983-05-04
DK157492B (da)	1990-01-15
DK140083A (da)	1984-06-04
FI831116A0 (fi)	1983-03-31
GB2132608A (en)	1984-07-11
IT1174758B (it)	1987-07-01
JPS59106483A (ja)	1984-06-20
JPH0439468B2 (de)	1992-06-29
GB2132608B (en)	1986-06-04
SE8301786D0 (sv)	1983-03-30
ZA832697B (en)	1983-12-28

Legal Events

Date	Code	Title	Description
1998-08-14	PFA	Name/firm changed	Owner name: ROUSSEL-UCLAF TRANSFER- ROUSSEL UCLAF * ROUSSEL UC
2002-11-29	PFA	Name/firm changed	Owner name: HOECHST MARION ROUSSEL TRANSFER- AVENTIS PHARMA S.
2003-05-15	PL	Patent ceased

Publication	Publication Date	Title
FR2692890A1 (fr)	1993-12-31	Procédé de préparation de la N-méthyl-3-phényl-3-[4-(trifluorométhyl)-phénoxy]-propylamine et de ses sels d'addition d'acide.
EP0331556A2 (de)	1989-09-06	Verfahren zur Herstellung von Ethylendiamin-N,N'-bis(ortho-hydroxyphenylessigsäure) und deren Derivate
EP0877726A1 (de)	1998-11-18	Verfahren zur acylierung einer aromatischen verbindung
FR2733980A1 (fr)	1996-11-15	Procede d'acylation d'ethers aromatiques non substitues
FR2821352A1 (fr)	2002-08-30	Procede de synthese de mono-ethers d'aryle et d'alkyle
EP0091385B1 (de)	1985-06-12	Verfahren zur Herstellung von p-Hydroxybenzylnitrilen oder p-Hydroxybenzylaminen
EP0102283A1 (de)	1984-03-07	Verfahren zur Herstellung von Quinuclidinderivaten substituiert in Stellung drei
CH653681A5 (fr)	1986-01-15	Procede de preparation de derives de l'acide 2-thiophene acetique.
CA1250313A (fr)	1989-02-21	PROCEDE DE PREPARATION DE COMPOSES INSATURES CHLORES EN .alpha. DE DEUX GROUPEMENTS ELECTROATTRACTEURS EN POSITION .beta.
EP0277894A2 (de)	1988-08-10	Verfahren zur Herstellung von Trialkoxybenzaldehyd
EP0013995B1 (de)	1982-12-29	Verfahren zur Herstellung acetylenischer macrocyclischer Ketone
FR2557098A1 (fr)	1985-06-28	Procede de preparation de bromobenzaldehydes hydroxy et/ou alkoxy substitues
EP0127536B1 (de)	1987-01-21	Verfahren zur Herstellung von alpha-delta-diethylenischen Carbonylverbindungen
EP0461972B1 (de)	1994-03-30	Verfahren zur Amwandlung von N-tertiären Aminoxiden in Aldehyden
EP0069001A1 (de)	1983-01-05	Verfahren zur Herstellung von 5,6,7,7a-Tetrahydro-4H-tieno (3,2-c) pyridin-2-onderivaten
CH655722A5 (fr)	1986-05-15	Procede de preparation de derives de l'acide 2-thiophene acetique.
EP0249556B1 (de)	1990-08-29	Herstellungsverfahren von alpha-halogenierten organischen Carbonatestern
EP0005654A1 (de)	1979-11-28	Isomerisierungsverfahren von 3-Vinyl-piperidinderivaten
EP0084743A1 (de)	1983-08-03	Verfahren zur Herstellung von alpha, alpha-difluoroalkoxy oder alpha, alphadifluoroalkylthiophenylsulfonen
FR2853901A1 (fr)	2004-10-22	Procede de preparation de derives de l'acide hexahydropyridazine-3-carboxylique
WO2025061989A1 (fr)	2025-03-27	Procédé de synthèse d'une benzophénone ou d'un dérivé d'une benzophénone
FR2725201A1 (fr)	1996-04-05	Procede de preparation de derives du nitrobenzene
FR2599030A1 (fr)	1987-11-27	Procede pour produire des anthraquinones.
CH420107A (fr)	1966-09-15	Procédé de préparation de nouveaux dérivés d'aralcoylaminoalcoylcyclohexanes substitués
BE896093A (fr)	1983-09-07	Procede d'obtention d'alpha-chloronitroso-alcanes dimeres et alpha-chloronitroso-alcanes dimeres obtenus par ledit procede