FR2470127A1 - Thienyl-2-glycolate de sodium racemique cristallise, son procede de preparation et son application a la fabrication de l'acide thienyl-2 acetique - Google Patents
Thienyl-2-glycolate de sodium racemique cristallise, son procede de preparation et son application a la fabrication de l'acide thienyl-2 acetique Download PDFInfo
- Publication number
- FR2470127A1 FR2470127A1 FR7928446A FR7928446A FR2470127A1 FR 2470127 A1 FR2470127 A1 FR 2470127A1 FR 7928446 A FR7928446 A FR 7928446A FR 7928446 A FR7928446 A FR 7928446A FR 2470127 A1 FR2470127 A1 FR 2470127A1
- Authority
- FR
- France
- Prior art keywords
- thienyl
- acid
- sodium
- glycolate
- racemic
- 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.)
- Granted
Links
- SMJRBWINMFUUDS-UHFFFAOYSA-N 2-thienylacetic acid Chemical compound OC(=O)CC1=CC=CS1 SMJRBWINMFUUDS-UHFFFAOYSA-N 0.000 title claims abstract description 13
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Divinylene sulfide Natural products C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 title claims description 9
- 229930192474 thiophene Natural products 0.000 title claims description 5
- 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 title description 10
- 239000011734 sodium Substances 0.000 title description 10
- 229910052708 sodium Inorganic materials 0.000 title description 10
- -1 thienyl glycolate Chemical compound 0.000 title description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims abstract description 39
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 21
- RTTVWPMGKSXOPD-UHFFFAOYSA-N C(CO)(=O)OC=1SC=CC1.[Na] Chemical compound C(CO)(=O)OC=1SC=CC1.[Na] RTTVWPMGKSXOPD-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000000706 filtrate Substances 0.000 claims abstract description 12
- 239000002253 acid Substances 0.000 claims abstract description 10
- 238000006243 chemical reaction Methods 0.000 claims description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 12
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 11
- 239000000243 solution Substances 0.000 claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 10
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 8
- 239000000725 suspension Substances 0.000 claims description 7
- WPWZFAUHXAPBFF-UHFFFAOYSA-N 2-hydroxy-2-thiophen-2-ylacetic acid Chemical compound OC(=O)C(O)C1=CC=CS1 WPWZFAUHXAPBFF-UHFFFAOYSA-N 0.000 claims description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 6
- 229940071870 hydroiodic acid Drugs 0.000 claims description 6
- 239000000047 product Substances 0.000 claims description 5
- AEMRFAOFKBGASW-UHFFFAOYSA-M Glycolate Chemical compound OCC([O-])=O AEMRFAOFKBGASW-UHFFFAOYSA-M 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 4
- YWQRBUWWNDNQBI-UHFFFAOYSA-N 2,2-dichloro-1-thiophen-2-ylethanone Chemical compound ClC(Cl)C(=O)C1=CC=CS1 YWQRBUWWNDNQBI-UHFFFAOYSA-N 0.000 claims description 3
- 235000019260 propionic acid Nutrition 0.000 claims description 3
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 159000000000 sodium salts Chemical class 0.000 claims description 2
- 238000005406 washing Methods 0.000 claims 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims 1
- 239000012670 alkaline solution Substances 0.000 claims 1
- 230000002641 glycemic effect Effects 0.000 claims 1
- 238000011065 in-situ storage Methods 0.000 claims 1
- FLXFOOZNPFNHSN-UHFFFAOYSA-N sodium 2H-thiophen-2-ide Chemical compound [Na+].C=1C=[C-]SC=1 FLXFOOZNPFNHSN-UHFFFAOYSA-N 0.000 claims 1
- 238000001291 vacuum drying Methods 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 3
- 239000003242 anti bacterial agent Substances 0.000 abstract description 2
- 229940088710 antibiotic agent Drugs 0.000 abstract description 2
- 238000003860 storage Methods 0.000 abstract description 2
- 239000007858 starting material Substances 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 229910052500 inorganic mineral Inorganic materials 0.000 description 5
- 239000011707 mineral Substances 0.000 description 5
- 238000001816 cooling Methods 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 239000011574 phosphorus Substances 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 125000001544 thienyl group Chemical group 0.000 description 3
- 229940015849 thiophene Drugs 0.000 description 3
- DBVGLIZLQMRBMY-UHFFFAOYSA-N 2-oxo-2-thiophen-2-ylacetaldehyde Chemical compound O=CC(=O)C1=CC=CS1 DBVGLIZLQMRBMY-UHFFFAOYSA-N 0.000 description 2
- 229930186147 Cephalosporin Chemical class 0.000 description 2
- 229930182555 Penicillin Natural products 0.000 description 2
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical class N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 229940124587 cephalosporin Drugs 0.000 description 2
- 150000001780 cephalosporins Chemical class 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 description 2
- 229910000043 hydrogen iodide Inorganic materials 0.000 description 2
- 229940049954 penicillin Drugs 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- XTUSEBKMEQERQV-UHFFFAOYSA-N propan-2-ol;hydrate Chemical compound O.CC(C)O XTUSEBKMEQERQV-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- CSZLZMBUJPLQQA-UHFFFAOYSA-N thiophen-2-yl 2-hydroxyacetate Chemical compound OCC(=O)OC1=CC=CS1 CSZLZMBUJPLQQA-UHFFFAOYSA-N 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- GIWRVUADKUVEGU-UHFFFAOYSA-N 2-oxo-2-thiophen-2-ylacetic acid Chemical compound OC(=O)C(=O)C1=CC=CS1 GIWRVUADKUVEGU-UHFFFAOYSA-N 0.000 description 1
- WSGYTJNNHPZFKR-UHFFFAOYSA-N 3-hydroxypropanenitrile Chemical compound OCCC#N WSGYTJNNHPZFKR-UHFFFAOYSA-N 0.000 description 1
- 206010022998 Irritability Diseases 0.000 description 1
- QTBSBXVTEAMEQO-GUEYOVJQSA-N acetic acid-d4 Chemical compound [2H]OC(=O)C([2H])([2H])[2H] QTBSBXVTEAMEQO-GUEYOVJQSA-N 0.000 description 1
- CSCPPACGZOOCGX-WFGJKAKNSA-N acetone d6 Chemical compound [2H]C([2H])([2H])C(=O)C([2H])([2H])[2H] CSCPPACGZOOCGX-WFGJKAKNSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000007942 carboxylates Chemical group 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000002089 crippling effect Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000007323 disproportionation reaction Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000007327 hydrogenolysis reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- MJGFBOZCAJSGQW-UHFFFAOYSA-N mercury sodium Chemical compound [Na].[Hg] MJGFBOZCAJSGQW-UHFFFAOYSA-N 0.000 description 1
- 238000004452 microanalysis Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- ZMRUPTIKESYGQW-UHFFFAOYSA-N propranolol hydrochloride Chemical compound [H+].[Cl-].C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 ZMRUPTIKESYGQW-UHFFFAOYSA-N 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- RUJQWQMCBPWFDO-UHFFFAOYSA-M silver;2-hydroxyacetate Chemical compound [Ag+].OCC([O-])=O RUJQWQMCBPWFDO-UHFFFAOYSA-M 0.000 description 1
- IFYZNXXDEGDTFO-UHFFFAOYSA-M sodium 2-hydroxy-2-thiophen-2-ylacetate Chemical compound S1C=CC=C1C(C(=O)[O-])O.[Na+] IFYZNXXDEGDTFO-UHFFFAOYSA-M 0.000 description 1
- 229910001023 sodium amalgam Inorganic materials 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 229940001584 sodium metabisulfite Drugs 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7928446A FR2470127A1 (fr) | 1979-11-19 | 1979-11-19 | Thienyl-2-glycolate de sodium racemique cristallise, son procede de preparation et son application a la fabrication de l'acide thienyl-2 acetique |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7928446A FR2470127A1 (fr) | 1979-11-19 | 1979-11-19 | Thienyl-2-glycolate de sodium racemique cristallise, son procede de preparation et son application a la fabrication de l'acide thienyl-2 acetique |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2470127A1 true FR2470127A1 (fr) | 1981-05-29 |
| FR2470127B1 FR2470127B1 (cg-RX-API-DMAC10.html) | 1983-04-15 |
Family
ID=9231830
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR7928446A Granted FR2470127A1 (fr) | 1979-11-19 | 1979-11-19 | Thienyl-2-glycolate de sodium racemique cristallise, son procede de preparation et son application a la fabrication de l'acide thienyl-2 acetique |
Country Status (1)
| Country | Link |
|---|---|
| FR (1) | FR2470127A1 (cg-RX-API-DMAC10.html) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2545086A1 (fr) * | 1983-04-29 | 1984-11-02 | Hoechst France | Procede de preparation d'acides alkanoiques |
| FR2588870A1 (fr) * | 1985-10-21 | 1987-04-24 | Hoechst France | Procede d'obtention d'acides alkanoiques |
| FR2588869A1 (fr) * | 1985-10-21 | 1987-04-24 | Hoechst France | Procede pour la fabrication d'acides alkanoiques |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2415109A1 (fr) * | 1977-03-11 | 1979-08-17 | Sagami Chem Res | Procedes de preparation de derives du thiophene et derives du thiophene obtenus au cours de ces procedes |
-
1979
- 1979-11-19 FR FR7928446A patent/FR2470127A1/fr active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2415109A1 (fr) * | 1977-03-11 | 1979-08-17 | Sagami Chem Res | Procedes de preparation de derives du thiophene et derives du thiophene obtenus au cours de ces procedes |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2545086A1 (fr) * | 1983-04-29 | 1984-11-02 | Hoechst France | Procede de preparation d'acides alkanoiques |
| EP0124407A1 (fr) * | 1983-04-29 | 1984-11-07 | SOCIETE FRANCAISE HOECHST Société anonyme dite: | Procédé de préparation d'acides alkanoiques |
| EP0265793A1 (fr) * | 1983-04-29 | 1988-05-04 | SOCIETE FRANCAISE HOECHST Société anonyme dite: | Procédé de préparation d'acides alkanoiques |
| FR2588870A1 (fr) * | 1985-10-21 | 1987-04-24 | Hoechst France | Procede d'obtention d'acides alkanoiques |
| FR2588869A1 (fr) * | 1985-10-21 | 1987-04-24 | Hoechst France | Procede pour la fabrication d'acides alkanoiques |
| EP0221815A1 (fr) * | 1985-10-21 | 1987-05-13 | SOCIETE FRANCAISE HOECHST Société anonyme dite: | Procédé pour la fabrication d'acides alkanoiques |
| EP0224401A1 (fr) * | 1985-10-21 | 1987-06-03 | SOCIETE FRANCAISE HOECHST Société anonyme dite: | Procédé d'obtention d'acides alkanoiques |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2470127B1 (cg-RX-API-DMAC10.html) | 1983-04-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |