AT392784B - Verfahren zur herstellung von derivaten der 2-thiophenessigsaeure - Google Patents
Verfahren zur herstellung von derivaten der 2-thiophenessigsaeure Download PDFInfo
- Publication number
- AT392784B AT392784B AT2866/83A AT286683A AT392784B AT 392784 B AT392784 B AT 392784B AT 2866/83 A AT2866/83 A AT 2866/83A AT 286683 A AT286683 A AT 286683A AT 392784 B AT392784 B AT 392784B
- Authority
- AT
- Austria
- Prior art keywords
- mixture
- compound
- formula
- toluene
- thienyl
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 title 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 90
- 150000001875 compounds Chemical class 0.000 claims description 56
- 238000000034 method Methods 0.000 claims description 39
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 34
- 239000000203 mixture Substances 0.000 claims description 29
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 238000002360 preparation method Methods 0.000 claims description 13
- 238000010992 reflux Methods 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- 239000012071 phase Substances 0.000 claims description 9
- 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 description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 229910052708 sodium Inorganic materials 0.000 claims description 8
- 239000011734 sodium Substances 0.000 claims description 8
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims description 8
- 150000002148 esters Chemical class 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- CQDGTJPVBWZJAZ-UHFFFAOYSA-N monoethyl carbonate Chemical compound CCOC(O)=O CQDGTJPVBWZJAZ-UHFFFAOYSA-N 0.000 claims description 6
- 150000001350 alkyl halides Chemical class 0.000 claims description 5
- 150000008051 alkyl sulfates Chemical class 0.000 claims description 5
- SMJRBWINMFUUDS-UHFFFAOYSA-N 2-thienylacetic acid Chemical compound OC(=O)CC1=CC=CS1 SMJRBWINMFUUDS-UHFFFAOYSA-N 0.000 claims description 4
- NJSUFZNXBBXAAC-UHFFFAOYSA-N ethanol;toluene Chemical compound CCO.CC1=CC=CC=C1 NJSUFZNXBBXAAC-UHFFFAOYSA-N 0.000 claims description 4
- 125000005910 alkyl carbonate group Chemical group 0.000 claims description 3
- 239000012141 concentrate Substances 0.000 claims description 3
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 238000006460 hydrolysis reaction Methods 0.000 claims description 3
- 239000008346 aqueous phase Substances 0.000 claims description 2
- 229940100198 alkylating agent Drugs 0.000 claims 3
- 239000002168 alkylating agent Substances 0.000 claims 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims 2
- 229910052938 sodium sulfate Inorganic materials 0.000 claims 2
- 235000011152 sodium sulphate Nutrition 0.000 claims 2
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 claims 1
- KTKWUKAYWFMQSO-UHFFFAOYSA-N 2-thiophen-2-ylpropanoic acid Chemical compound OC(=O)C(C)C1=CC=CS1 KTKWUKAYWFMQSO-UHFFFAOYSA-N 0.000 claims 1
- 150000008050 dialkyl sulfates Chemical class 0.000 claims 1
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 claims 1
- 229940008406 diethyl sulfate Drugs 0.000 claims 1
- 238000004821 distillation Methods 0.000 claims 1
- 238000001035 drying Methods 0.000 claims 1
- CEFSVYOPCJUCQP-UHFFFAOYSA-N methyl sulfo sulfate Chemical compound COS(=O)(=O)OS(O)(=O)=O CEFSVYOPCJUCQP-UHFFFAOYSA-N 0.000 claims 1
- GPTFURBXHJWNHR-UHFFFAOYSA-N protopine Chemical compound C1=C2C(=O)CC3=CC=C4OCOC4=C3CN(C)CCC2=CC2=C1OCO2 GPTFURBXHJWNHR-UHFFFAOYSA-N 0.000 claims 1
- 239000002585 base Substances 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000002904 solvent Substances 0.000 description 6
- 230000035484 reaction time Effects 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 229910000104 sodium hydride Inorganic materials 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 101100490437 Mus musculus Acvrl1 gene Proteins 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical group 0.000 description 2
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 229930192474 thiophene Natural products 0.000 description 2
- 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
- FIPWRIJSWJWJAI-UHFFFAOYSA-N Butyl carbitol 6-propylpiperonyl ether Chemical compound C1=C(CCC)C(COCCOCCOCCCC)=CC2=C1OCO2 FIPWRIJSWJWJAI-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 229930186147 Cephalosporin Natural products 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241000251730 Chondrichthyes Species 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 206010027626 Milia Diseases 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 1
- 150000008046 alkali metal hydrides Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 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
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229940124587 cephalosporin Drugs 0.000 description 1
- 150000001780 cephalosporins Chemical class 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 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
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 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
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229960005235 piperonyl butoxide Drugs 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- -1 thienyl 2-acetic acid Chemical compound 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 150000003577 thiophenes Chemical class 0.000 description 1
- 239000008096 xylene 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
- C07D333/24—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)
- 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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8220271A FR2537137B1 (fr) | 1982-12-03 | 1982-12-03 | Procede de preparation de derives de l'acide 2-thiophene acetique et produits intermediaires necessaires pour leur preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| ATA286683A ATA286683A (de) | 1990-11-15 |
| AT392784B true AT392784B (de) | 1991-06-10 |
Family
ID=9279757
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT2866/83A AT392784B (de) | 1982-12-03 | 1983-08-08 | Verfahren zur herstellung von derivaten der 2-thiophenessigsaeure |
Country Status (22)
| Country | Link |
|---|---|
| JP (1) | JPS59106482A (en]) |
| KR (1) | KR900005681B1 (en]) |
| AT (1) | AT392784B (en]) |
| AU (1) | AU556803B2 (en]) |
| BE (1) | BE896439A (en]) |
| CA (1) | CA1201441A (en]) |
| CH (2) | CH659817A5 (en]) |
| DE (1) | DE3314029A1 (en]) |
| DK (2) | DK160427C (en]) |
| ES (1) | ES521230A0 (en]) |
| FI (1) | FI83646C (en]) |
| FR (1) | FR2537137B1 (en]) |
| GB (1) | GB2132607B (en]) |
| HU (1) | HU192136B (en]) |
| IE (1) | IE55075B1 (en]) |
| IT (1) | IT1174757B (en]) |
| LU (1) | LU84748A1 (en]) |
| NL (1) | NL8301692A (en]) |
| NZ (1) | NZ204509A (en]) |
| PT (1) | PT76534B (en]) |
| SE (2) | SE453992B (en]) |
| ZA (1) | ZA832698B (en]) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2083961T3 (es) * | 1988-04-22 | 1996-05-01 | Byk Gulden Lomberg Chem Fab | Acidos 3-anilino-2-hidroxicarbonil-4-tiofenoaceticos. |
| IT1276738B1 (it) * | 1995-06-16 | 1997-11-03 | Erregierre Spa | Processo per la preparazione di derivati dell'acido -metil-2- tiofeneacetico |
| DE102004008807A1 (de) | 2004-02-20 | 2005-09-08 | Bayer Cropscience Ag | Pyrazolopyrimidine |
| CN113896709B (zh) * | 2021-11-22 | 2023-02-28 | 南京一苇医药科技有限公司 | 一种苯并噻吩-3-乙酸的合成方法 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1919381A1 (de) * | 1968-04-16 | 1969-10-23 | Ici Ltd | Heterocyclische Verbindungen und Verfahren zu deren Herstellung |
| GB2003570A (en) * | 1977-06-08 | 1979-03-14 | Imi Opella Ltd | Branch pipe connections |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB683337A (en) * | 1949-10-01 | 1952-11-26 | Warner Hudnut Inc | Improvements in or relating to the preparation of antispasmodic compounds |
| FR2260575A1 (en) * | 1974-02-11 | 1975-09-05 | Innothera Lab Sa | Cyclohexyl 3-thienyl acetic acid prodn - from methyl 3-thienylacetate through diethyl cyclohexyl 3-thienyl malonate as starting material for basic esters as drugs |
| FR2421897A1 (fr) * | 1978-04-04 | 1979-11-02 | Labaz | Nouveaux derives du thiophene, leur procede de preparation ainsi que les compositions therapeutiques les contenant |
-
1982
- 1982-12-03 FR FR8220271A patent/FR2537137B1/fr not_active Expired
-
1983
- 1983-03-28 DK DK139983A patent/DK160427C/da not_active IP Right Cessation
- 1983-03-30 SE SE8301785A patent/SE453992B/sv not_active IP Right Cessation
- 1983-03-31 FI FI831115A patent/FI83646C/fi not_active IP Right Cessation
- 1983-04-05 ES ES521230A patent/ES521230A0/es active Granted
- 1983-04-11 PT PT76534A patent/PT76534B/pt not_active IP Right Cessation
- 1983-04-12 CH CH4155/85A patent/CH659817A5/fr not_active IP Right Cessation
- 1983-04-12 CH CH1967/83A patent/CH655722A5/fr not_active IP Right Cessation
- 1983-04-12 BE BE0/210536A patent/BE896439A/fr unknown
- 1983-04-14 LU LU84748A patent/LU84748A1/fr unknown
- 1983-04-14 HU HU831308A patent/HU192136B/hu not_active IP Right Cessation
- 1983-04-15 AU AU13574/83A patent/AU556803B2/en not_active Ceased
- 1983-04-18 DE DE19833314029 patent/DE3314029A1/de active Granted
- 1983-04-18 ZA ZA832698A patent/ZA832698B/xx unknown
- 1983-04-23 KR KR1019830001729A patent/KR900005681B1/ko not_active Expired
- 1983-05-04 IT IT48215/83A patent/IT1174757B/it active
- 1983-05-09 GB GB08312701A patent/GB2132607B/en not_active Expired
- 1983-05-10 IE IE1075/83A patent/IE55075B1/en not_active IP Right Cessation
- 1983-05-11 NL NL8301692A patent/NL8301692A/nl active Search and Examination
- 1983-05-20 JP JP58087835A patent/JPS59106482A/ja active Granted
- 1983-06-09 NZ NZ204509A patent/NZ204509A/en unknown
- 1983-07-28 CA CA000433421A patent/CA1201441A/fr not_active Expired
- 1983-08-08 AT AT2866/83A patent/AT392784B/de not_active IP Right Cessation
-
1987
- 1987-09-09 SE SE8703494A patent/SE457724B/sv not_active IP Right Cessation
-
1990
- 1990-06-06 DK DK138490A patent/DK164550C/da not_active IP Right Cessation
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1919381A1 (de) * | 1968-04-16 | 1969-10-23 | Ici Ltd | Heterocyclische Verbindungen und Verfahren zu deren Herstellung |
| GB2003570A (en) * | 1977-06-08 | 1979-03-14 | Imi Opella Ltd | Branch pipe connections |
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| Date | Code | Title | Description |
|---|---|---|---|
| ELJ | Ceased due to non-payment of the annual fee |