FI62684B - FREQUENCY REFRIGERATION OF 2- (2-AMINO-EECL) -THIOPHENE - Google Patents
FREQUENCY REFRIGERATION OF 2- (2-AMINO-EECL) -THIOPHENE Download PDFInfo
- Publication number
- FI62684B FI62684B FI790121A FI790121A FI62684B FI 62684 B FI62684 B FI 62684B FI 790121 A FI790121 A FI 790121A FI 790121 A FI790121 A FI 790121A FI 62684 B FI62684 B FI 62684B
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- Prior art keywords
- thiophene
- process according
- electrolyte
- organic
- aminoethyl
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- 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
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
- C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
- C25B3/00—Electrolytic production of organic compounds
- C25B3/20—Processes
- C25B3/25—Reduction
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Electrochemistry (AREA)
- Materials Engineering (AREA)
- Metallurgy (AREA)
- Electrolytic Production Of Non-Metals, Compounds, Apparatuses Therefor (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
rrm. L -.’I fa, .... KU ULUTUSJULKAISURRM. L -. ’I fa, .... KU RELEASE PUBLICATION
jffl[φ ^ ^ UTLÄGGNI NGSSKRIFT 62 684 5¾¾ C Patentti, cylnnetly 10 02 1983 • (45) Patent codde-lit (Si) Kv.ik.3/I«.a3 C 25 B 3/04 SUOMI —FINLAND (il) ΝΜΜΜίΜΐι-ΜιιΜηιβΜιιι T90121 (22) Hak»ml*pUvt—Aiw&knlnpdkf 15.01.79 ^^ (23) Alkupaivt—GHtlfhmdaf 15.01.79 (41) Tulkit |MlklMkil — MMt offamHg 26.07.79jffl [φ ^ ^ UTLÄGGNI NGSSKRIFT 62 684 5¾¾ C Patent, cylnnetly 10 02 1983 • (45) Patent codde-lit (Si) Kv.ik.3 / I «.a3 C 25 B 3/04 FINLAND —FINLAND (il) ΝΜΜΜίΜΐι-ΜιιΜηιβΜιιι T90121 (22) Hak »ml * pUvt — Aiw & knlnpdkf 15.01.79 ^^ (23) Alkupaivt — GHtlfhmdaf 15.01.79 (41) Translators | MlklMkil - MMt offamHg 26.07.79
Mntti- ja r«ki*t«rihalittu· NihUviMpwon |. kmAjultatam pvm.- 2Q 10 82Mntti- ja r «ki * t« rihalittu · NihUviMpwon |. kmAjultatam pvm.- 2Q 10 82
Patant- och rf l«tfityral—n ' ' AmMcm utJtfd odi wlakrUkM puMleararf y' (32)(33)(31) Pyr4«*ty «nothin >uW pftartw 25.01.7Ö Ranska-Frankrike(FR) 7801992 (71) Parcor, U0, avenue Georges V, 75008 Paris, Ranska-Frankrike(FR) (72) Urbain Henri Emile Braye, Lagardelle/Leze, Ranska-Frankrike(FR) (7*0 Oy Kolster Ab (5**) Menetelmä 2-(2-amino-etyyli)-tiofeenin sähkökemialliseksi valmistamiseksi - Förfarande för elektrokemisk framställning av 2-(2-amino-etyl)--tiofen Tämä keksintö kohdistuu menetelmään 2-(2-amino-etyyli)-tio-feenin sähkökemialliseksi valmistamiseksi, jonka kaava on [f"SV|— CH2-CH2-NIi2 2-(2-amino-etyyli)-tiofeeni on välituote, jota käytetään tienopyridiinijohdannaisten synteesissä, jotka vaikuttavat erikoisesti verihiutaleiden kasaantumista estävästi, tulehduksia vastustavina aineina ja verisuonia laajentavasti ja joita on esitelty FR-patentissa 2 215 948 ja sen ensimmäisessä lisäpatentissa 2 345 150.Patant- och rf l «tfityral — n '' AmMcm utJtfd odi wlakrUkM puMleararf y '(32) (33) (31) Pyr4« * ty «nothin> uW pftartw 25.01.7Ö France-France (FR) 7801992 (71) Parcor , U0, avenue Georges V, 75008 Paris, France-France (FR) (72) Urbain Henri Emile Braye, Lagardelle / Leze, France-France (FR) (7 * 0 Oy Kolster Ab (5 **) Method 2- ( The present invention relates to a process for the electrochemical preparation of 2- (2-aminoethyl) thiophene of the formula: (2-Aminoethyl) thiophene for the electrochemical preparation of 2- (2-aminoethyl) thiophene is [f "SV | - CH 2 -CH 2 -Ni 2 2- (2-aminoethyl) -thiophene is an intermediate used in the synthesis of thienopyridine derivatives which have a special anti-platelet, anti-inflammatory and vasodilatory effect and which have been shown in FR- in U.S. Patent 2,215,948 and its first additional patent 2,345,150.
Keksinnölle on tunnusomaista, että 2-(2-nitro-vinyyli)-tiofeeni, jonka kaava on |ΓΥ~2 pelkistetään sähkökemiallisesti orgaanisessa tai vesipitoisessa orgaanisessa väliaineessa elektrolyytin läsnäollessa happamessa pH-arvossa ja 5-40°C:n lämpötilassa ja että haluttu tuote otetaan talteen reaktio HC'Oa SC S tA .The invention is characterized in that 2- (2-nitro-vinyl) -thiophene of the formula | ΓΥ ~ 2 is electrochemically reduced in an organic or aqueous organic medium in the presence of an electrolyte at an acidic pH and a temperature of 5-40 ° C and that the desired product recover the reaction HC'Oa SC S tA.
o 62 68 4o 62 68 4
Tuotteen talteenotto suoritetaan edullisesti orgaanisen liuottimen avulla elektrolyytin neutraloinnin jälkeen.The recovery of the product is preferably carried out with the aid of an organic solvent after neutralization of the electrolyte.
Orgaanisen väliaineen täytyy pystyä liuottamaan lähtömateriaali, so. 2-(2-nitro-vinyyli)-tiofeeni ja voi se olla esimerkiksi etikkahappo, dioksaani tai metanoli.The organic medium must be able to dissolve the starting material, i. 2- (2-nitro-vinyl) -thiophene and may be, for example, acetic acid, dioxane or methanol.
Tämän keksinnön suositeltavassa toteutuksessa käytetään vesialkoholi-väliainetta, joka sisältää 20-70 paino-% orgaanista liuotinta ja edullisesti 50% orgaanista liuotinta sisältävää seosta, kuten vesi-etikkahapposeosta suhteessa 50:50.In a preferred embodiment of the present invention, an aqueous alcohol medium containing 20 to 70% by weight of an organic solvent and preferably a mixture containing 50% by weight of an organic solvent, such as a 50:50 mixture of water and acetic acid, is used.
Sähkökemiallinen pelkistys suoritetaan potentiaalissa 1,1 ΟΙ ,30 V mitattuna kyllästetyn kalomeli-vertailuelektrodin suhteen ja edullisesti potentaalissa noin 1,15 V.The electrochemical reduction is performed at a potential of 1.1 ΟΙ.30 V measured with respect to a saturated calomel reference electrode and preferably at a potential of about 1.15 V.
Reaktioseoksen pH-arvon täytyy olla hapan ja edullisesti on se noin 2. Mainittu pH-arvo voidaan saada lisäämällä voimakasta mineraalihappoa, kuten suolahappoa ja sopivan puskurin (sitraatti-HC1, esimerkiksi) avulla.The pH of the reaction mixture should be acidic and preferably about 2. Said pH can be obtained by adding a strong mineral acid such as hydrochloric acid and a suitable buffer (citrate HCl, for example).
Elektrolyytti lisätään orgaaniseen tai vesi-orgaaniseen väliaineeseen sähkökemiallisen reaktion suorittamiseksi ja on se tyypillisesti alkalimetalUkloridi, kuten natrium- tai litiumkloridi sopivana pitoisuutena, tavallisesti 0,2-0,7 moolia/litra ja edullisesti 0,5 moolia/litra.The electrolyte is added to an organic or aqueous-organic medium to carry out the electrochemical reaction and is typically an alkali metal chloride such as sodium or lithium chloride in a suitable concentration, usually 0.2 to 0.7 mol / liter and preferably 0.5 mol / liter.
Sopiva reaktioseoksen lämpötila on 5-40°C ja edullisesti käytetään huoneenlämpötilaa.A suitable temperature of the reaction mixture is 5-40 ° C and room temperature is preferably used.
2-(2-nitro-vinyyli)-tiofeenin pitoisuus reaktioväliaineessa on edullisesti välillä 1 g/1 ja 10 g/1 ja edullisesti välillä 1 g/i ja 3 2/1.The concentration of 2- (2-nitrovinyl) thiophene in the reaction medium is preferably between 1 g / l and 10 g / l and preferably between 1 g / l and 3 2/1.
Työelektrodiksi sähkökemialliseen kennoon suositellaan materiaalia, jonka vedyn ylijännite on suuri, kuten elohopeaa, sinkkiä tai lyijyä, jolloin elohopeakerros on suositeltava.As the working electrode for the electrochemical cell, a material with a high hydrogen overvoltage, such as mercury, zinc or lead, is recommended, in which case a mercury layer is recommended.
Tämän keksinnön muut piirteet ilmenevät seuraavasta esityksestä, jossa viitataan mukaaniiitetyn piirroksen ainoaan kuvioon, jonka tarkoitus on pelkästään kuvaava.Other features of the present invention will become apparent from the following description, in which reference is made to the sole drawing of the accompanying drawing, which is for illustrative purposes only.
2-(2-nitro-vinyyli)-tiofeenin sähkökemiallinen pelkistys voidaan suorittaa esimerkiksi kuviossa esitetyssä kennossa.The electrochemical reduction of 2- (2-nitro-vinyl) -thiophene can be performed, for example, in the cell shown in the figure.
Mainittu kenno 1 on jaettu elektrolyysiosastoon 2 ja anodi-osastoon 3, jotka on erotettu toisistaan huokoisen, esimerkiksi sintrattua lasia olevan seinän 4 avulla sähkön kulun takaamiseksi. Platina- tai grafiittielektrodi 5 toimii anodina ja elektrodi 6Said cell 1 is divided into an electrolysis compartment 2 and an anode compartment 3, which are separated from each other by a porous wall 4, for example sintered glass, to ensure the flow of electricity. The platinum or graphite electrode 5 acts as the anode and the electrode 6
3 f, ? ^ 8 A3 f,? ^ 8 A
(tai työelektrodi) on sijoitettu pohjalle tai lähelle elektrolyy-siosaston pohjaa. Kennon 1 osastoon 2 on sijoitettu sekoituslaite reaktioväliainetta varten, joka laite kuvan toteutuksessa on mag-neettitanko 7 sijoitettuna lähelle kennon pohjaa.(or working electrode) is located at or near the bottom of the electrolysis compartment. A mixing device for the reaction medium is placed in the compartment 2 of the cell 1, which device in the implementation of the image is a magnetic rod 7 placed close to the bottom of the cell.
Kenno on varustettu myös inertin kaasun syöttöputkella 8 elektrolyyttiliuoksen pinnan alapuolelle ja poistoputkella 9 mainittua kaasua varten kennon kannessa 10.The cell is also provided with an inert gas supply pipe 8 below the surface of the electrolyte solution and an outlet pipe 9 for said gas in the cell cover 10.
Vertailuelektrodi 11 on sijoitettu kennon ulkopuolelle niin, että reaktiotuotteet eivät likaa sitä sähköisen yhteyden ollessa sillan 12 kautta, joka muodostuu kolmitieventtiilistä 13 ja putkesta 14, joka on suljettu katodiosastoon 2 ulottuvalla sintratul-la lasilla. Seuraavan esimerkin tarkoitus on esitellä keksintöä.The reference electrode 11 is located outside the cell so that the reaction products do not contaminate it when the electrical connection is through a bridge 12 consisting of a three-way valve 13 and a tube 14 closed by a sintered glass extending into the cathode compartment 2. The following example is intended to illustrate the invention.
Esimerkki 2-(2-nitro-vinyyli)-tiofeenin sähkökemiallinen pelkistys suoritetaan platina-anodin sisältävässä kennossa, joka sisältää myös elohopeakerroksen muodostaman työelektrodin tai katodin.Example The electrochemical reduction of 2- (2-nitro-vinyl) -thiophene is carried out in a cell containing a platinum anode, which also contains a working electrode or cathode formed by a mercury layer.
Reaktioseos on etikkahappo-vesi-seos suhteessa 50:50 ja elektrolyyttinä käytetään 0,5 molaarista litiumkloridiliuosta.The reaction mixture is a 50:50 acetic acid-water mixture and a 0.5 molar lithium chloride solution is used as the electrolyte.
Pelkistyspotentiaali pidetään 1,150 voltissa kyllästetyn kalomelielektrodin suhteen ja reaktio suoritetaan huoneenlämpö-tilassa. 2-(2-nitro-vinyyli)-tiofeeniä lisätään vesi-orgaaniseen väliaineeseen niin, että alkuväkevyys on 2,5 g/1.The reduction potential is maintained at 1,150 volts with respect to the saturated calomel electrode and the reaction is carried out at room temperature. 2- (2-Nitrovinyl) -thiophene is added to the aqueous-organic medium to an initial concentration of 2.5 g / l.
Kennossa ylläpidetään typpiatmosfääriä ja pelkistys suoritetaan sitten sekoittaen johtamalla sähkövirta sen lävitse etukäteen määrätyllä jännitteellä.A nitrogen atmosphere is maintained in the cell and the reduction is then performed with stirring by conducting an electric current therethrough at a predetermined voltage.
Elektrolyysin päätyttyä (2500 coulombin jälkeen) neutraloidaan katodiosaston elektrolyytti, uutetaan kloroformilla ja pestään sitten vedellä ja kuivataan vedettömän K2CO.j:n yläpuolella. Haluttu amiini otetaan talteen hydrokloridina tai oksalaattina etanolissa.At the end of the electrolysis (after 2500 Coulombs), the electrode of the cathode compartment is neutralized, extracted with chloroform and then washed with water and dried over anhydrous K2CO.j. The desired amine is recovered as the hydrochloride or oxalate in ethanol.
2-(2-amino-etyyli)-tiofeeni saanto on 47% lähtömateriaalista laskettuna. Tämä saanto vastaa myös faradista saantoa, koska läpi-kulkenut sähkömäärä vastaa 100% transformaatiota.The yield of 2- (2-aminoethyl) thiophene is 47% based on the starting material. This yield also corresponds to a faradic yield because the amount of electricity passed corresponds to 100% transformation.
Claims (10)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7801992A FR2415671A1 (en) | 1978-01-25 | 1978-01-25 | PROCESS FOR PREPARING 2-AMINO 2-ETHYL-2-THIOPHENE BY ELECTROCHEMICAL METHOD |
| FR7801992 | 1978-01-25 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI790121A FI790121A (en) | 1979-07-26 |
| FI62684B true FI62684B (en) | 1982-10-29 |
| FI62684C FI62684C (en) | 1983-02-10 |
Family
ID=9203795
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI790121A FI62684C (en) | 1978-01-25 | 1979-01-15 | FREQUENCY REFRIGERATION OF 2- (2-AMINO-EECL) -THIOPHENE |
Country Status (19)
| Country | Link |
|---|---|
| EP (1) | EP0003446B1 (en) |
| JP (1) | JPS6046190B2 (en) |
| AR (1) | AR220736A1 (en) |
| AT (1) | AT364839B (en) |
| BE (1) | BE873677A (en) |
| CH (1) | CH635618A5 (en) |
| DE (1) | DE2960070D1 (en) |
| DK (1) | DK151904C (en) |
| ES (1) | ES476659A1 (en) |
| FI (1) | FI62684C (en) |
| FR (1) | FR2415671A1 (en) |
| GB (1) | GB2013196B (en) |
| GR (1) | GR65325B (en) |
| IE (1) | IE47783B1 (en) |
| IT (1) | IT1115135B (en) |
| LU (1) | LU80772A1 (en) |
| MX (1) | MX5460E (en) |
| NO (1) | NO151715C (en) |
| PT (1) | PT69105A (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5191090A (en) * | 1990-01-25 | 1993-03-02 | Syntex (U.S.A.) Inc. | Preparation of 2-(2'-thienyl)ethylamine derivatives and synthesis of thieno[3,2-c]pyridine derivatives therefrom |
| JP7229710B2 (en) | 2018-09-26 | 2023-02-28 | 本田技研工業株式会社 | VEHICLE CONTROL DEVICE, VEHICLE CONTROL METHOD, AND PROGRAM |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2299332A1 (en) * | 1975-01-31 | 1976-08-27 | Parcor | PROCESS FOR PREPARING (THIENYL-2) -2-ETHYLAMINE AND ITS DERIVATIVES |
-
1978
- 1978-01-25 FR FR7801992A patent/FR2415671A1/en active Granted
- 1978-12-22 GR GR57970A patent/GR65325B/en unknown
-
1979
- 1979-01-04 DE DE7979400005T patent/DE2960070D1/en not_active Expired
- 1979-01-04 EP EP79400005A patent/EP0003446B1/en not_active Expired
- 1979-01-08 CH CH12079A patent/CH635618A5/en not_active IP Right Cessation
- 1979-01-09 ES ES476659A patent/ES476659A1/en not_active Expired
- 1979-01-10 LU LU80772A patent/LU80772A1/en unknown
- 1979-01-12 DK DK013879A patent/DK151904C/en not_active IP Right Cessation
- 1979-01-15 FI FI790121A patent/FI62684C/en not_active IP Right Cessation
- 1979-01-17 AR AR275192A patent/AR220736A1/en active
- 1979-01-18 AT AT0038379A patent/AT364839B/en not_active IP Right Cessation
- 1979-01-19 PT PT7969105A patent/PT69105A/en unknown
- 1979-01-23 IT IT47735/79A patent/IT1115135B/en active
- 1979-01-24 BE BE0/193053A patent/BE873677A/en unknown
- 1979-01-24 NO NO790231A patent/NO151715C/en unknown
- 1979-01-24 GB GB7902545A patent/GB2013196B/en not_active Expired
- 1979-01-24 MX MX797680U patent/MX5460E/en unknown
- 1979-01-25 JP JP54008103A patent/JPS6046190B2/en not_active Expired
- 1979-01-30 IE IE112/79A patent/IE47783B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ATA38379A (en) | 1981-04-15 |
| CH635618A5 (en) | 1983-04-15 |
| AR220736A1 (en) | 1980-11-28 |
| FR2415671A1 (en) | 1979-08-24 |
| JPS54117462A (en) | 1979-09-12 |
| IE790112L (en) | 1979-07-25 |
| GB2013196B (en) | 1982-06-23 |
| ES476659A1 (en) | 1979-05-16 |
| JPS6046190B2 (en) | 1985-10-15 |
| AT364839B (en) | 1981-11-25 |
| DK151904B (en) | 1988-01-11 |
| LU80772A1 (en) | 1979-05-16 |
| PT69105A (en) | 1979-02-01 |
| IE47783B1 (en) | 1984-06-13 |
| FI62684C (en) | 1983-02-10 |
| EP0003446A1 (en) | 1979-08-08 |
| EP0003446B1 (en) | 1980-11-26 |
| GB2013196A (en) | 1979-08-08 |
| FI790121A (en) | 1979-07-26 |
| FR2415671B1 (en) | 1981-11-20 |
| GR65325B (en) | 1980-08-11 |
| NO151715C (en) | 1985-05-22 |
| DK151904C (en) | 1988-06-06 |
| DK13879A (en) | 1979-07-26 |
| BE873677A (en) | 1979-07-24 |
| IT7947735A0 (en) | 1979-01-23 |
| NO151715B (en) | 1985-02-11 |
| DE2960070D1 (en) | 1981-02-12 |
| IT1115135B (en) | 1986-02-03 |
| NO790231L (en) | 1979-07-26 |
| MX5460E (en) | 1983-08-11 |
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| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: PARCOR |