NO151715B - PROCEDURE FOR ELECTRO-CHEMICAL PREPARATION OF 2- (2-AMINOETHYL) THIOPHEN - Google Patents
PROCEDURE FOR ELECTRO-CHEMICAL PREPARATION OF 2- (2-AMINOETHYL) THIOPHEN Download PDFInfo
- Publication number
- NO151715B NO151715B NO790231A NO790231A NO151715B NO 151715 B NO151715 B NO 151715B NO 790231 A NO790231 A NO 790231A NO 790231 A NO790231 A NO 790231A NO 151715 B NO151715 B NO 151715B
- Authority
- NO
- Norway
- Prior art keywords
- thiophene
- organic
- aminoethyl
- medium
- nitrovinyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 13
- HVLUYXIJZLDNIS-UHFFFAOYSA-N 2-thiophen-2-ylethanamine Chemical compound NCCC1=CC=CS1 HVLUYXIJZLDNIS-UHFFFAOYSA-N 0.000 title claims description 7
- UTPOWFFIBWOQRK-ONEGZZNKSA-N 2-[(e)-2-nitroethenyl]thiophene Chemical compound [O-][N+](=O)\C=C\C1=CC=CS1 UTPOWFFIBWOQRK-ONEGZZNKSA-N 0.000 claims description 8
- 239000012429 reaction media Substances 0.000 claims description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- 239000003792 electrolyte Substances 0.000 claims description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- ZOMNIUBKTOKEHS-UHFFFAOYSA-L dimercury dichloride Chemical class Cl[Hg][Hg]Cl ZOMNIUBKTOKEHS-UHFFFAOYSA-L 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 claims description 4
- 229910052753 mercury Inorganic materials 0.000 claims description 4
- PQLVXDKIJBQVDF-UHFFFAOYSA-N acetic acid;hydrate Chemical compound O.CC(O)=O PQLVXDKIJBQVDF-UHFFFAOYSA-N 0.000 claims description 3
- 229910001514 alkali metal chloride Inorganic materials 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 229910052697 platinum Inorganic materials 0.000 claims description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 2
- 229910002804 graphite Inorganic materials 0.000 claims description 2
- 239000010439 graphite Substances 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- 229910052725 zinc Inorganic materials 0.000 claims description 2
- 239000011701 zinc Substances 0.000 claims description 2
- 238000000605 extraction Methods 0.000 claims 1
- 238000006386 neutralization reaction Methods 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- -1 2-AMINOETHYL Chemical class 0.000 abstract 1
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 abstract 1
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 238000005868 electrolysis reaction Methods 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- IKRZCYCTPYDXML-UHFFFAOYSA-N 2-hydroxypropane-1,2,3-tricarboxylic acid;hydrochloride Chemical compound Cl.OC(=O)CC(O)(C(O)=O)CC(O)=O IKRZCYCTPYDXML-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 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 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 238000003487 electrochemical reaction Methods 0.000 description 1
- 239000008151 electrolyte solution Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Inorganic materials [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
- DBDCNCCRPKTRSD-UHFFFAOYSA-N thieno[3,2-b]pyridine Chemical class C1=CC=C2SC=CC2=N1 DBDCNCCRPKTRSD-UHFFFAOYSA-N 0.000 description 1
- 229940124549 vasodilator Drugs 0.000 description 1
- 239000003071 vasodilator agent 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
- C07D333/14—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
Landscapes
- 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)
Abstract
FREMGANGSMÅTE FOR ELEKTROKJEMISK FREMSTILLING AV 2-(2-AMINOETHYL)-THIOFEN.PROCEDURE FOR ELECTROCHEMICAL PREPARATION OF 2- (2-AMINOETHYL) THIOFEN.
Description
Foreliggende oppfinnelse angår en fremgangsmåte for elektrokjemisk fremstilling av 2-(2-aminoethyl)-thiofen. The present invention relates to a method for the electrochemical production of 2-(2-aminoethyl)-thiophene.
2-(2-aminoethyl)-thiofen er et mellomprodukt som anvendes ved fremstilling av thienopyridinderivater som i sær-deleshet utviser en inhiberende virkning på blodplateaggregering, anti-inflammatorisk aktivitet og vasodilatoraktivitet og som er beskrevet i fransk patentskrift 2 215 948 og tilleggspatent 2 345 150. 2-(2-aminoethyl)-thiophene is an intermediate used in the production of thienopyridine derivatives which, in particular, exhibit an inhibitory effect on platelet aggregation, anti-inflammatory activity and vasodilator activity and which is described in French patent document 2 215 948 and supplementary patent 2 345 150.
Oppfinnelsen angår således en fremgangsmåte ved fremstilling av 2-(2-aminoethyl)-thiofen av formel: hvilken fremgangsmåte er kjennetegnet ved at 2-(2-nitrovinyl)-thiofen av formel: The invention thus relates to a process for the production of 2-(2-aminoethyl)-thiophene of formula: which process is characterized in that 2-(2-nitrovinyl)-thiophene of formula:
i et organisk eller vandig-organisk medium reduseres elektrokjemisk ved et potensial på 1,10-1,30 V, fortrinnsvis ved 1,15 V, målt i forhold til en mettet calomel referanseelektrode, i nærvær av et alkalimetallklorid i en konsentrasjon på in an organic or aqueous-organic medium is reduced electrochemically at a potential of 1.10-1.30 V, preferably at 1.15 V, measured relative to a saturated calomel reference electrode, in the presence of an alkali metal chloride in a concentration of
0,2-0,7 mol/l, fortrinnsvis 0,5 mol/l, som elektrolytt, og til-stedeværende ved en pH på 2 og en temperatur mellom 5 og 40°C, hvoretter det ønskede produkt utvinnes fra reaksjonsmediet. 0.2-0.7 mol/l, preferably 0.5 mol/l, as electrolyte, and present at a pH of 2 and a temperature between 5 and 40°C, after which the desired product is recovered from the reaction medium.
Det organiske medium skal være slik at det tillater oppløsning av utgangsmaterialet, dvs. 2-(2-nitrovinyl)-thiofen, og kan f.eks. være eddiksyre, dioxan eller methanol. The organic medium must be such that it allows dissolution of the starting material, i.e. 2-(2-nitrovinyl)-thiophene, and can e.g. be acetic acid, dioxane or methanol.
Ifølge en foretrukken utførelsesform av oppfinnelsen anvendes det et vandig-alkoholisk medium omfattende 20 - 70 vekt% organisk løsningsmiddel og fortrinnsvis en blanding omfattende 50% organisk løsningsmiddel, slik som en vann-eddiksyreblanding (50:50). According to a preferred embodiment of the invention, an aqueous-alcoholic medium is used comprising 20-70% by weight organic solvent and preferably a mixture comprising 50% organic solvent, such as a water-acetic acid mixture (50:50).
Den elektrokjemiske reduksjon utføres ved et potensial på 1,10 - 1,30 V i forhold til en mettet calomel referanseelektrode, og fortrinnsvis ved et potensial på ca. 1,15 V. The electrochemical reduction is carried out at a potential of 1.10 - 1.30 V in relation to a saturated calomel reference electrode, and preferably at a potential of approx. 1.15V.
pH på reaksjonsmediet skal være ved en verdi på 2. The pH of the reaction medium must be at a value of 2.
Denne pH kan oppnås ved tilsetning av en sterk uorganisk syre This pH can be achieved by adding a strong inorganic acid
slik som saltsyre eller ved hjelp av en egnet buffer (eksempelvis citrat-HCl). such as hydrochloric acid or by means of a suitable buffer (for example citrate-HCl).
Elektrolytten tilsettes til det organiske eller vandig-organiske medium for å bevirke den elektrokjemiske reaksjon og er typisk et alkalimetallklorid slik som natrium eller lithiumklorid, ved en egnet konsentrasjon på 0,2 - 0,7 mol/liter, og fortrinnsvis 0,5 mol/liter. The electrolyte is added to the organic or aqueous-organic medium to effect the electrochemical reaction and is typically an alkali metal chloride such as sodium or lithium chloride, at a suitable concentration of 0.2 - 0.7 mol/litre, and preferably 0.5 mol/ litres.
En egnet reaksjonstemperatur på reaksjonsmediet er mellom 5 og 40°C, fortrinnsvis 15 - 25°C. A suitable reaction temperature of the reaction medium is between 5 and 40°C, preferably 15 - 25°C.
Konsentrasjonen av 2-(2-nitrovinyl)-thiofen i reaksjonsmediet er mellom 1 g/l og 10 g/l, og fortrinnsvis mellom 1 g/l og 3 g/l. The concentration of 2-(2-nitrovinyl)-thiophene in the reaction medium is between 1 g/l and 10 g/l, and preferably between 1 g/l and 3 g/l.
Som arbeidselektrode for den elektrokjemiske celle anvendes et materiale med en høy hydrogenoverspenning, slik som kvikksølv, sink eller bly, og et kvikksølvlag foretrekkes. A material with a high hydrogen overvoltage, such as mercury, zinc or lead, is used as the working electrode for the electrochemical cell, and a mercury layer is preferred.
Andre trekk ved oppfinnelsen fremgår fra den etterføl-gende beskrivelse under henvisning til den medfølgende tegning. Other features of the invention appear from the following description with reference to the accompanying drawing.
Den elektrokjemiske reduksjon av 2-(2-nitrovinyl)-thiofen kan utføres i en celle slik som den som er vist på tegningen. The electrochemical reduction of 2-(2-nitrovinyl)-thiophene can be carried out in a cell such as that shown in the drawing.
Cellen 1 er oppdelt i et elektrolysekammer 2 og et ano-dekammer 3 som er adskilt av en porøs vegg 4, eksempelvis av sintret glass, for å sikre elektrisk ledning. En platina-eller grafittelektrode 5 tjener som en anode, mens elektroden 6 (eller arbeidselektroden) er anordnet ved bunnen eller nær bunnen i elektrolysekammeret. Cellen 1 er i dets kammer 2 utstyrt med en omrøringsanordning for reaksjonsmediet, som i den viste utførel-sesform er en magnetstav 7 anordnet i umiddelbar nærhet av bunnen av cellen. The cell 1 is divided into an electrolysis chamber 2 and an anode chamber 3 which are separated by a porous wall 4, for example of sintered glass, to ensure electrical conduction. A platinum or graphite electrode 5 serves as an anode, while the electrode 6 (or working electrode) is arranged at or near the bottom of the electrolysis chamber. The cell 1 is equipped in its chamber 2 with a stirring device for the reaction medium, which in the embodiment shown is a magnetic rod 7 arranged in the immediate vicinity of the bottom of the cell.
Cellen er også utstyrt med et inertgassinnløp 8 neden-for nivået av elektrolyttløsningen, og med et utløp 9 for gassen i lokket 10 av cellen. The cell is also equipped with an inert gas inlet 8 below the level of the electrolyte solution, and with an outlet 9 for the gas in the lid 10 of the cell.
En referanseelektrode 11 er plassert på utsiden av cellen for å forhindre forurensning med reduksjonsproduktene, idet den elektriske forbindelse skjer gjennom en bro 12 omfattende en treveisventil 13 og et rør 14 lukket med sintret glass som er dyppet ned i katodekammeret 2. A reference electrode 11 is placed on the outside of the cell to prevent contamination with the reduction products, the electrical connection being through a bridge 12 comprising a three-way valve 13 and a tube 14 closed with sintered glass which is immersed in the cathode chamber 2.
Det etterfølgende eksempel illustrerer oppfinnelsen. The following example illustrates the invention.
Eksempel Example
Den elektrokjemiske reduksjon av 2-(2-nitrovinyl)-thio-fen utføres i en celle inneholdende en platinaanode og arbeidselektroden eller katoden er et kvikksølvlag. The electrochemical reduction of 2-(2-nitrovinyl)-thiophene is carried out in a cell containing a platinum anode and the working electrode or cathode is a layer of mercury.
Reaksjonsmediet er en eddiksyre-vann (50:50) blanding og 0,5 molar lithiumklorid anvendes som elektrolytt. The reaction medium is an acetic acid-water (50:50) mixture and 0.5 molar lithium chloride is used as electrolyte.
Reduksjonspotensialet holdes ved 1,150 V i forhold til en mettet calomel elektrode, og reaksjonen utføres ved romtempe-ratur . The reduction potential is kept at 1.150 V in relation to a saturated calomel electrode, and the reaction is carried out at room temperature.
2-(2-nitrovinyl)-thiofenet tilsettes til det vandig-organiske medium ved en begynnelseskonsentrasjon på 2,5 g/l. The 2-(2-nitrovinyl)-thiophene is added to the aqueous-organic medium at an initial concentration of 2.5 g/l.
Cellen holdes under nitrogenatmosfære og reduksjonen utføres under omrøring ved å føre strømmen ved den på forhånd bestemte spenning. The cell is kept under a nitrogen atmosphere and the reduction is carried out with stirring by passing the current at the predetermined voltage.
Ved endt elektrolyse (etter passasje av 2500 coulomb) nøytraliseres elektrolytten i katodekammeret, ekstraheres med kloroform og vaskes deretter med vann og tørkes over vannfritt I^CO^. Det ønskede amin gjenvinnes som hydrokloridet eller oxa-latet i ethanol. At the end of electrolysis (after passage of 2500 coulombs), the electrolyte in the cathode chamber is neutralized, extracted with chloroform and then washed with water and dried over anhydrous I^CO^. The desired amine is recovered as the hydrochloride or oxalate in ethanol.
Utbyttet av 2-(2-aminoethyl)-thiofen er 47% på basis The yield of 2-(2-aminoethyl)-thiophene is 47% on a basis
av utgangsmaterialet. Dette utbytte svarer til Faradays utbytte, of the starting material. This yield corresponds to Faraday's yield,
da mengden av passert elektrisitet er den som svarer til en 100% overføring. as the amount of electricity passed is the one that corresponds to a 100% transfer.
Claims (8)
Applications Claiming Priority (1)
| 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 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO790231L NO790231L (en) | 1979-07-26 |
| NO151715B true NO151715B (en) | 1985-02-11 |
| NO151715C NO151715C (en) | 1985-05-22 |
Family
ID=9203795
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO790231A NO151715C (en) | 1978-01-25 | 1979-01-24 | PROCEDURE FOR ELECTRO-CHEMICAL PREPARATION OF 2- (2-AMINOETHYL) THIOPHEN. |
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 |
| FI62684B (en) | 1982-10-29 |
| 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 |
| DE2960070D1 (en) | 1981-02-12 |
| IT1115135B (en) | 1986-02-03 |
| NO790231L (en) | 1979-07-26 |
| MX5460E (en) | 1983-08-11 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Gramstad et al. | 33. Perfluoroalkyl derivatives of sulphur. Part IV. Perfluoroalkanesulphonic acids | |
| Nematollahi et al. | Electro-oxidation of catechols in the presence of benzenesulfinic acid. Application to electro-organic synthesis of new sulfone derivatives | |
| US4714530A (en) | Method for producing high purity quaternary ammonium hydroxides | |
| Pickett et al. | A study of the production of glyoxylic acid by the electrochemical reduction of oxalic acid solutions | |
| O'Connor et al. | Voltammetry and Controlled Potential Oxidation of 3, 4‐Dimethoxypropenylbenzene at a Rotating Platinum Electrode in Unbuffered Acetonitrile and in Acetonitrile‐Pyridine Solution | |
| US4588484A (en) | Electrochemical reduction of 3-chlorobenzo[b]thiophenes | |
| NO151715B (en) | PROCEDURE FOR ELECTRO-CHEMICAL PREPARATION OF 2- (2-AMINOETHYL) THIOPHEN | |
| Coetzee et al. | Voltammetry in methanol, ethanol, and sulfolane as solvents | |
| Berkenkotter et al. | Anodic Oxidation of N, N, N'‐Triphenyl‐o‐Phenylenediamine | |
| Tabaković et al. | Electrochemical synthesis of heterocyclic compounds. Part 6. The redox behaviour of the formazan–tetrazolium salt system in acetonitrile | |
| Jeroschewski et al. | Investigation on the mechanism of the electrochemical reduction of CS2 in aprotic solvents | |
| Ruettinger et al. | Electrochemical carboxylation of ketene S, S-acetals | |
| Tallec et al. | Electrochemical reduction of 1-aryl-4-nitroazoles | |
| Davarani et al. | An improved electrochemical method for the synthesis of some benzofuran derivatives | |
| Marrosu et al. | Electroreduction of N-benzyl-N-nitrosoanthranilic acid to 1-benzyl-1, 2-dihydro-3H-indazol-3-one | |
| US3687826A (en) | Electrolytic reduction of polyhaloquinoline and polyhaloisoquinoline | |
| Winslow | Porous Carbon Electrodes: III. Reduction of p‐Nitraniline | |
| JPH02185989A (en) | Electric syntesis of aldehyde | |
| Fotouhi et al. | Electro‐Oxidation of 3, 4‐Dihydroxybenzoic Acid in the Presence of 6‐Methyl‐1, 2, 4‐Triazine‐3‐Thione‐5‐One: Unique Synthesis of 7H‐Thiazolo [3, 2‐b]‐1, 2, 4‐Triazin‐7‐One Derivative in Aqueous Media | |
| ES2204310B2 (en) | PROCEDURE FOR OBTAINING 4-ISOQUINOLINOL FROM 1-ISOQUINOLINIC ACID OR ITS CARBOXYLATE BY ELECTROCHEMICAL METHODS. | |
| Hlavatý et al. | Electrolytically initiated intramolecular cyclization of 2-nitrobiphenyl-2'-carboxylic acid | |
| SU1162797A1 (en) | Method of obtaining 2,2,6,6-tetramethyl-4-aminopiperidine-1-oxyl | |
| Andruzzi et al. | On the electrochemical reduction mechanism of indolinone nitroxide radicals in DMF | |
| Griggio | Electrochemical reduction mechanism of sulfilimines: S, S-diphenyl-Np-nitrobenzenesulfonylsulfilimine | |
| Griggio et al. | Electrochemical reduction of some sulfilimines |