LU84749A1 - Procede de preparation de derives del'acide 2-thiophene acetique - Google Patents

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

Info

Publication number: LU84749A1
Authority: LU; Luxembourg
Prior art keywords: formula; product; thiophene; iii; preparation
Prior art date: 1982-12-03

Application number

LU84749A

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

1983-04-14

Publication date

1983-12-05

1983-04-14 Application filed by Roussel Uclaf filed Critical Roussel Uclaf

1983-12-05 Publication of LU84749A1 publication Critical patent/LU84749A1/fr

Links

238000000034 method Methods 0.000 title claims description 30
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 title claims description 29
239000002253 acid Substances 0.000 title claims description 12
238000002360 preparation method Methods 0.000 title claims description 12
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 39
229930192474 thiophene Natural products 0.000 claims description 15
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 12
150000001299 aldehydes Chemical class 0.000 claims description 10
238000006243 chemical reaction Methods 0.000 claims description 9
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
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
239000003054 catalyst Substances 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
239000000243 solution Substances 0.000 claims description 6
VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 claims description 6
GEDJSTBRFXDCAM-UHFFFAOYSA-N 2-(1-chloroethyl)thiophene Chemical compound CC(Cl)C1=CC=CS1 GEDJSTBRFXDCAM-UHFFFAOYSA-N 0.000 claims description 5
125000004432 carbon atom Chemical group C* 0.000 claims description 5
125000005843 halogen group Chemical group 0.000 claims description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
238000006276 transfer reaction Methods 0.000 claims description 5
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 4
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 4
230000007062 hydrolysis Effects 0.000 claims description 4
238000006460 hydrolysis reaction Methods 0.000 claims description 4
239000003444 phase transfer catalyst Substances 0.000 claims description 4
239000003795 chemical substances by application Substances 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
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 3
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
229910052783 alkali metal Inorganic materials 0.000 claims description 2
150000001342 alkaline earth metals Chemical class 0.000 claims description 2
239000007864 aqueous solution Substances 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
150000005395 2-thiopheneacetic acid derivatives Chemical class 0.000 claims 1
150000001340 alkali metals Chemical group 0.000 claims 1
VBQDSLGFSUGBBE-UHFFFAOYSA-N benzyl(triethyl)azanium Chemical compound CC[N+](CC)(CC)CC1=CC=CC=C1 VBQDSLGFSUGBBE-UHFFFAOYSA-N 0.000 claims 1
239000000047 product Substances 0.000 description 42
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 39
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
239000002904 solvent Substances 0.000 description 12
239000000203 mixture Substances 0.000 description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
-1 alkyl radical Chemical class 0.000 description 9
239000008346 aqueous phase Substances 0.000 description 8
239000012074 organic phase Substances 0.000 description 8
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
238000010992 reflux Methods 0.000 description 6
239000012071 phase Substances 0.000 description 5
238000003756 stirring Methods 0.000 description 5
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-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
239000002585 base Substances 0.000 description 3
239000003153 chemical reaction reagent Substances 0.000 description 3
238000000605 extraction Methods 0.000 description 3
229910052736 halogen Inorganic materials 0.000 description 3
239000005457 ice water Substances 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
150000005394 2-thiopheneacetic acids Chemical class 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-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
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
229910000147 aluminium phosphate Inorganic materials 0.000 description 2
125000004429 atom Chemical group 0.000 description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
239000007810 chemical reaction solvent Substances 0.000 description 2
150000002367 halogens Chemical class 0.000 description 2
LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
239000011591 potassium Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
150000003577 thiophenes Chemical class 0.000 description 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 description 1
SMJRBWINMFUUDS-UHFFFAOYSA-N 2-thienylacetic acid Chemical compound OC(=O)CC1=CC=CS1 SMJRBWINMFUUDS-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
239000002841 Lewis acid Substances 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
239000004721 Polyphenylene oxide Substances 0.000 description 1
241001620634 Roger Species 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
239000003513 alkali Substances 0.000 description 1
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical class Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 1
230000003110 anti-inflammatory effect Effects 0.000 description 1
VUEDNLCYHKSELL-UHFFFAOYSA-N arsonium Chemical class [AsH4+] VUEDNLCYHKSELL-UHFFFAOYSA-N 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
244000309464 bull Species 0.000 description 1
ZQULWKDLLXZZSP-UHFFFAOYSA-N calcium cyanide Chemical class [Ca+2].N#[C-].N#[C-] ZQULWKDLLXZZSP-UHFFFAOYSA-N 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
238000003459 chloroalkylation reaction Methods 0.000 description 1
150000003983 crown ethers Chemical class 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
230000026030 halogenation Effects 0.000 description 1
238000005658 halogenation reaction Methods 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
239000003456 ion exchange resin Substances 0.000 description 1
229920003303 ion-exchange polymer Polymers 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
150000007517 lewis acids Chemical class 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical group [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
229940127557 pharmaceutical product Drugs 0.000 description 1
XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
229920000570 polyether Polymers 0.000 description 1
229940072033 potash Drugs 0.000 description 1
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
235000015320 potassium carbonate Nutrition 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
239000012266 salt solution Substances 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000003760 tallow Substances 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000005207 tetraalkylammonium group Chemical group 0.000 description 1
DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 1
RKHXQBLJXBGEKF-UHFFFAOYSA-M tetrabutylphosphanium;bromide Chemical compound [Br-].CCCC[P+](CCCC)(CCCC)CCCC RKHXQBLJXBGEKF-UHFFFAOYSA-M 0.000 description 1
TVVPMLFGPYQGTG-UHFFFAOYSA-M tetramethylphosphanium;iodide Chemical compound [I-].C[P+](C)(C)C TVVPMLFGPYQGTG-UHFFFAOYSA-M 0.000 description 1
OSBSFAARYOCBHB-UHFFFAOYSA-N tetrapropylammonium Chemical group CCC[N+](CCC)(CCC)CCC OSBSFAARYOCBHB-UHFFFAOYSA-N 0.000 description 1
230000007704 transition Effects 0.000 description 1
239000013638 trimer Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 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)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Catalysts (AREA)

LU84749A 1982-12-03 1983-04-14 Procede de preparation de derives del'acide 2-thiophene acetique LU84749A1 (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR8220272		1982-12-03
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
LU84749A1 true LU84749A1 (fr)	1983-12-05

Family

ID=9279758

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
LU84749A LU84749A1 (fr)	1982-12-03	1983-04-14	Procede de preparation de derives del'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 BE BE0/210537A patent/BE896440A/fr unknown
- 1983-04-12 CH CH1966/83A patent/CH653681A5/fr not_active IP Right Cessation
- 1983-04-14 LU LU84749A patent/LU84749A1/fr unknown
- 1983-04-14 HU HU831307A patent/HU191831B/hu unknown
- 1983-04-15 AU AU13573/83A patent/AU557065B2/en not_active Ceased
- 1983-04-18 DE DE3314028A patent/DE3314028C2/de not_active Expired - Lifetime
- 1983-04-18 ZA ZA832697A patent/ZA832697B/xx unknown
- 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
ATA286783A (de)	1990-11-15
IT1174758B (it)	1987-07-01
HU191831B (en)	1987-04-28
NL8301693A (nl)	1984-07-02
GB2132608A (en)	1984-07-11
JPH0439468B2 (de)	1992-06-29
PT76535B (fr)	1986-03-12
IT8348216A0 (it)	1983-05-04
KR900003281B1 (ko)	1990-05-12
SE8301786L (sv)	1984-06-04
FI831116L (fi)	1984-06-04
GB8312702D0 (en)	1983-06-15
PT76535A (fr)	1983-05-01
BE896440A (fr)	1983-10-12
ES8401958A1 (es)	1984-01-01
NZ204510A (en)	1986-02-21
DK157492C (da)	1990-06-11
FI80882B (fi)	1990-04-30
ES521231A0 (es)	1984-01-01
CH653681A5 (fr)	1986-01-15
GB2132608B (en)	1986-06-04
ZA832697B (en)	1983-12-28
IE831074L (en)	1984-06-03
JPS59106483A (ja)	1984-06-20
IE55097B1 (en)	1990-05-23
DK140083D0 (da)	1983-03-28
AU557065B2 (en)	1986-12-04
FI831116A0 (fi)	1983-03-31
AT392785B (de)	1991-06-10
DK157492B (da)	1990-01-15
SE8301786D0 (sv)	1983-03-30
DK140083A (da)	1984-06-04
FI80882C (fi)	1990-08-10
FR2537138A1 (fr)	1984-06-08
AU1357383A (en)	1984-06-07
FR2537138B1 (de)	1985-05-24
DE3314028A1 (de)	1984-06-07
SE453918B (sv)	1988-03-14
DE3314028C2 (de)	1995-05-24
KR840006987A (ko)	1984-12-04

Publication	Publication Date	Title
CA2196586C (fr)	2008-06-03	Preparation du 1,1,1,3,3-pentachlorobutane et du 1,1,1,3,3-pentafluorobutane
BE1006426A6 (fr)	1994-08-23	Procede de preparation de la n-methyl-3-phenyl-3-[4-(trifluoromethyl)-phenoxy]-propylamine et de ses sels d'addition d'acide.
EP0283359B1 (de)	1990-09-12	Verfahren zur Herstellung von Ketonen
EP0030528B1 (de)	1983-06-22	Verfahren zur Einführung von Alkyl-Aralkyl-Cycloalkylgruppen in eine Funktionsgruppe enthaltende Kohlenstoffkette
EP0965588B1 (de)	2004-03-10	Verfahren zur Herstellung von 4-phenyl-1,2,3,6-tetrahydropyridin-derivaten und die dafür verwendeten Zwischenprodukte
LU84749A1 (fr)	1983-12-05	Procede de preparation de derives del'acide 2-thiophene acetique
JPH06340567A (ja)	1994-12-13	ジフルオルメトキシアレン及びジフルオルメチルチオアレンの製造法
EP0013995B1 (de)	1982-12-29	Verfahren zur Herstellung acetylenischer macrocyclischer Ketone
EP0200840B1 (de)	1989-04-05	Verfahren zur Herstellung von gegebenenfalls in 5-Stellung halogenisierten 6-(Nieder)-alkoxy-1-naphthoesäuren und den entsprechenden Estern
EP0149952B1 (de)	1987-07-08	Verfahren zur Herstellung von Brombenzaldehyden-Hydroxy und/oder Alkoxy substituiert
EP1140785B1 (de)	2004-12-29	Verfahren zur herstellung von polyhalogenierten para-trifluoroanilinen
EP0171320A1 (de)	1986-02-12	Herstellungsverfahren von ungesättigten, in alpha-chlorierten Verbindungen von zwei in beta-Stellung elektronenanziehenden Gruppen
JPH06340571A (ja)	1994-12-13	シクロペンテノンの製造方法
CH659817A5 (fr)	1987-02-27	Derives de l'acide 2-thiophene acetique et leur preparation.
FR2655039A1 (fr)	1991-05-31	Synthese des bromures de perfluoroalkyle.
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
EP0249556B1 (de)	1990-08-29	Herstellungsverfahren von alpha-halogenierten organischen Carbonatestern
EP0888318A1 (de)	1999-01-07	Verbessertes verfahren zur herstellung von 3-(10-phenothiazin)- oder 3-(10-phenoxazin)-propansäure-derivate
EP0260472B1 (de)	1991-03-13	Verfahren zur Herstellung von cycloaliphatischen Ketonen
CH621784A5 (de)	1981-02-27
EP0950052B1 (de)	2004-09-08	Verfahren zur herstellung eines tetrahydropyridinderivates
LU84129A1 (fr)	1984-03-07	Procede d'halogenation en meta de n-(o,o'-dialkyl phenyl)alaninates et homologues
CH666257A5 (fr)	1988-07-15	Procede de preparation de 2-halogeno-resorcinols.
FR2787787A1 (fr)	2000-06-30	Procede de preparation de thioethers aromatiques de type diphenyle