DK151904B - METHOD OF ELECTROCHEMICAL PREPARATION OF 2- (2-AMINOETHYL) THIOPHEN - Google Patents
METHOD OF ELECTROCHEMICAL PREPARATION OF 2- (2-AMINOETHYL) THIOPHEN Download PDFInfo
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- DK151904B DK151904B DK013879AA DK13879A DK151904B DK 151904 B DK151904 B DK 151904B DK 013879A A DK013879A A DK 013879AA DK 13879 A DK13879 A DK 13879A DK 151904 B DK151904 B DK 151904B
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- organic
- thiophene
- aminoethyl
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- 238000000034 method Methods 0.000 title claims description 16
- HVLUYXIJZLDNIS-UHFFFAOYSA-N 2-thiophen-2-ylethanamine Chemical compound NCCC1=CC=CS1 HVLUYXIJZLDNIS-UHFFFAOYSA-N 0.000 title claims description 10
- 238000002360 preparation method Methods 0.000 title claims description 4
- 230000008569 process Effects 0.000 claims description 12
- 239000012429 reaction media Substances 0.000 claims description 8
- 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 7
- 239000003792 electrolyte Substances 0.000 claims description 7
- 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
- 239000002609 medium 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 group ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 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
- 239000003960 organic solvent Substances 0.000 claims description 4
- -1 2- (2-aminoethyl) -thiophenyl Chemical group 0.000 claims description 3
- PQLVXDKIJBQVDF-UHFFFAOYSA-N acetic acid;hydrate Chemical compound O.CC(O)=O PQLVXDKIJBQVDF-UHFFFAOYSA-N 0.000 claims description 3
- 230000002378 acidificating effect Effects 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
- ZOMNIUBKTOKEHS-UHFFFAOYSA-L dimercury dichloride Chemical class Cl[Hg][Hg]Cl ZOMNIUBKTOKEHS-UHFFFAOYSA-L 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
- 239000012736 aqueous medium Substances 0.000 claims description 2
- 238000000605 extraction Methods 0.000 claims description 2
- 229910002804 graphite Inorganic materials 0.000 claims description 2
- 239000010439 graphite Substances 0.000 claims description 2
- 238000006386 neutralization reaction Methods 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
- 239000002904 solvent Substances 0.000 claims 1
- 230000009467 reduction Effects 0.000 description 7
- 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
- 239000007858 starting material Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 238000005868 electrolysis reaction Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- SXJFHUAMIQJDNX-UHFFFAOYSA-N 2-ethenyl-2-nitro-3h-thiophene Chemical compound [O-][N+](=O)C1(C=C)CC=CS1 SXJFHUAMIQJDNX-UHFFFAOYSA-N 0.000 description 1
- 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
- HLPRKWVEMYDPAU-UHFFFAOYSA-N 2-thiophen-2-ylethyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCCC1=CC=CS1 HLPRKWVEMYDPAU-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
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000011109 contamination 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
- 231100001261 hazardous Toxicity 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 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
- 238000011946 reduction process Methods 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
- 230000007928 solubilization Effects 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
- 230000000153 supplemental effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 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
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 230000000304 vasodilatating 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
- C07D333/14—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)
Description
iin
DK 151904 BDK 151904 B
Den foreliggende opfindelse angår en fremgangsmåde til elektrokemisk fremstilling af 2-(2-aminoethyl)-thiophen.The present invention relates to a process for the electrochemical preparation of 2- (2-aminoethyl) thiophene.
2-(2-aminoethyl)-thiophen er et mellemprodukt, der benyttes 5 til syntese af thienopyridinderivater, som især har inhibe-rende virkning på blodpladeaggregationen samt antiinflamma-toriske og vasodilatoriske virkninger, og som er omhandlet i fransk patentskrift nr. 2.215.948 og beskrivelsen til det dertil hørende tillægspatent nr. 2.345.150.2- (2-Aminoethyl) -thiophene is an intermediate used for the synthesis of thienopyridine derivatives, which have especially inhibitory action on platelet aggregation as well as anti-inflammatory and vasodilatory effects, and are disclosed in French Patent No. 2,215,948. and the description of the accompanying supplemental patent No. 2,345,150.
1010
Pra S. Gronovitz og F. Sandberg: "Arkiv, for Kemi, 1970, 32, 217" er det kendt at fremstille 2-(2-aminoethyl)-thiophen ved reduktion af 3-nitrovinyl-2-thiophen med lithiumaluminium-hydrid, men dette reagens er dyrt og vanskeligt at håndtere 15 i industriel skala, så at mange forholdsregler må træffes ved dets anvendelse. Fremgangsmåden ifølge fransk patentskrift nr. 2.299.332, ved hvilken 2-(2-aminoethyl)-thiophen eller 2-(2-thienyl)-ethylamin blev fremstillet i to trin ud fra 2-(2-thienyl)-ethyl-p-toluensulfonat med'et udbytte på 34%, 20 repræsenterer en forbedring i forhold til den nævnte kendte reduktionsproces, men p-toluensulfonatderivatet skal være fremstillet i forvejen, f.eks. ved fremgangsmåden ifølge fransk patentskrift nr. 2.300.090, der resulterer i et udbytte på 72%. Det samlede udbytte ved den forbedrede fremgangsmåde 25 er derfor under 30%.Pra S. Gronovitz and F. Sandberg: "Archives, for Chemistry, 1970, 32, 217" it is known to prepare 2- (2-aminoethyl) thiophene by reduction of 3-nitrovinyl-2-thiophene with lithium aluminum hydride, but this reagent is expensive and difficult to handle on an industrial scale, so that many precautions must be taken in its use. The process of French Patent No. 2,299,332 in which 2- (2-aminoethyl) thiophene or 2- (2-thienyl) ethylamine was prepared in two steps from 2- (2-thienyl) ethyl-p toluene sulfonate with the yield of 34%, 20 represents an improvement over the known reduction process, but the p-toluenesulfonate derivative must be prepared in advance, e.g. by the method of French Patent No. 2,300,090 resulting in a yield of 72%. Therefore, the overall yield of the improved process 25 is below 30%.
Det har nu vist sig, at man ved fremgangsmåden ifølge opfindelsen kan fremstille 2-(2-aminoethyl)-thiophen ud fra 2-(2-nitro-vinyl)-thiophen i et udbytte på 47% i et trin ved anvendelse 30 af elektrokemisk reduktion af udgangsmaterialet.It has now been found that in the process of the invention, 2- (2-aminoethyl) thiophene can be prepared from 2- (2-nitro-vinyl) thiophene in 47% yield in one step using electrochemical 30 reduction of the starting material.
Den foreliggende opfindelse angår således en fremgangsmåde til fremstilling af 2-(2-aminoethyl)-thiophen med formlen I ch2-ch2-nh2 35 2Thus, the present invention relates to a process for the preparation of 2- (2-aminoethyl) thiophene of formula I ch2-ch2-nh2
DK 151904 BDK 151904 B
hvilken fremgangsmåde er ejendommelig ved, at man elektrokemisk reducerer 2-(2-nitrovinyl)-thiophen med formlen ^ S\ - [ ]τ- ch=ch-no9 i_I! ved et potentiale på 1,10-1,30 volt, målt i forhold til en mættet kalomel-referenceelektrode, fortrinsvis ved 1,15 volt, i et organisk eller organisk-vandigt medium i nærværelse af j^Q et alkalimetalchlorid i en koncentration på 0,2-0,7 mol/1, fortrinsvis 0,5 mol/1, som elektrolyt ved en sur pH-værdi og ved en temperatur mellem 5°C og 40°C, og at man udvinder det ønskede produkt fra reaktionsmediet. Udvinding af produktet foretages fordelagtigt ved hjælp af et organisk opløsnings-15 middel efter neutralisation af elektrolytten.which method is characterized by electrochemically reducing 2- (2-nitrovinyl) -thiophene of the formula ^ S \ - [] τ- ch = ch-no9 i_I! at a potential of 1.10-1.30 volts, measured relative to a saturated calomel reference electrode, preferably at 1.15 volts, in an organic or organic aqueous medium in the presence of 1 M a alkali metal chloride at a concentration of 0.2-0.7 mol / l, preferably 0.5 mol / l, as electrolyte at an acidic pH and at a temperature between 5 ° C and 40 ° C and recovering the desired product from the reaction medium. Advantageous extraction of the product is carried out by means of an organic solvent after neutralization of the electrolyte.
Det organiske medium bør være et sådant, som muliggør solubili-sering af udgangsmaterialet, dvs. 2-(2-nitrovinyl)-thiophen, og det kan eksempelvis være eddikesyre, dioxan eller methanol.The organic medium should be one which allows solubilization of the starting material, i.e. 2- (2-nitrovinyl) -thiophene, and it may be, for example, acetic acid, dioxane or methanol.
2020
Ifølge en foretrukken udførelsesform for opfindelsen gøres der brug af et vandigt-alkoholisk medium omfattende 20-70 vægt% organisk opløsningsmiddel, fortrinsvis en blanding omfattende 50% organisk opløsningsmiddel, såsom en vand-eddike-25 syreblanding (50:50). jAccording to a preferred embodiment of the invention, an aqueous-alcoholic medium comprising 20-70% by weight of organic solvent is used, preferably a mixture comprising 50% organic solvent, such as a water-acetic acid mixture (50:50). j
Reaktionsmediets pH-værdi skal ligge i det sure område og fortrinsvis ved pH ca. 2. Denne pH-værdi kan opnås ved tilsætning af en stærk uorganisk syre, såsom saltsyre, eller ved 3Q hjælp af en pasende puffer (citrat-HCl, f.eks.).The pH of the reaction medium should be in the acidic range and preferably at pH ca. 2. This pH can be obtained by the addition of a strong inorganic acid such as hydrochloric acid or by a suitable buffer (citrate-HCl, for example).
Elektrolytten sættes til det organiske eller vandigt-organiske medium til gennemførelse af den elektrokemiske reak- 35 3The electrolyte is added to the organic or aqueous-organic medium to carry out the electrochemical reaction.
DK 151904BDK 151904B
tion og er et alkalimetalchlorid, såsom natrium- eller lithium-chlorid, til en passende koncentration, som en 0,2-0,7 mol/1, og fortrinsvis 0,5 mol/1.is an alkali metal chloride, such as sodium or lithium chloride, to an appropriate concentration, such as 0.2-0.7 mol / l, and preferably 0.5 mol / l.
g En passende temperatur i reaktionsmediet ligger mellem 5°C og 40°C, og det foretrækkes at anvende stuetemperatur.g An appropriate temperature in the reaction medium is between 5 ° C and 40 ° C, and room temperature is preferred.
Koncentrationen af 2-nitro-2-vinyl-thiophen i reaktionsmediet ligger fordelagtigt mellem 1 g/1 og 10 g/1, fortrinsvis mellem 1Q 1 g/1 og 3 g/1.The concentration of 2-nitro-2-vinyl-thiophene in the reaction medium is advantageously between 1 g / l and 10 g / l, preferably between 1 and 1 g / l and 3 g / l.
Som arbejdselektrode for den elektrokemiske celle benyttes et materiale med en høj hydrogenoverspænding, såsom kviksølv, zink eller bly, idet et kviksølvlag foretrækkes.As the working electrode of the electrochemical cell, a material with a high hydrogen overvoltage such as mercury, zinc or lead is used, with a mercury layer being preferred.
1515
Opfindelsen forklares nærmere i den efterfølgende beskrivelse i forbindelse med figuren på tegningen.The invention is explained in more detail in the following description in connection with the figure in the drawing.
Den elektrokemiske reduktion af 2-(2-nitrovinyl)-thiophen 20 kan udføres i en celle, som den på tegningen viste.The electrochemical reduction of 2- (2-nitrovinyl) -thiophene 20 can be carried out in a cell as shown in the drawing.
Denne celle 1 er delt i et elektrolysekammer 2 og et anodekammer 3, hvilke kamre er adskilt ved hjælp af en porøs væg 4 af eksempelvis sintret glas til sikring af elektrisk led-25 ning. En platin- eller grafitelektrode 5 fungerer som anode, medens en elektrode 6 (eller arbejdselektrode) er placeret ved bunden eller nær ved bunden af elektrolysekammeret. Cellen 1 er i kammeret 2 udstyret med et omrørerorgan for reaktionsmediet, og i den viste udførelsesform er en magnetstang 30 7 placeret i nærheden af cellebunden.This cell 1 is divided into an electrolysis chamber 2 and anode chamber 3, which chambers are separated by a porous wall 4 of, for example, sintered glass to secure electrical conduction. A platinum or graphite electrode 5 acts as an anode while an electrode 6 (or working electrode) is located at the bottom or near the bottom of the electrolytic chamber. The cell 1 is provided in the chamber 2 with a stirring means for the reaction medium, and in the embodiment shown, a magnetic rod 30 7 is located near the cell bottom.
Cellen er også indrettet med et indløb 8 for indifferent gas under elektrolytopløsningens overflade og har et udløb 9 for denne gas i cellelåget 10.The cell is also provided with an inert gas inlet 8 below the surface of the electrolyte solution and has an outlet 9 for this gas in the cell lid 10.
En referenceelektrode 11 er placeret uden for cellen med henblik på hindring af forurening med reduktionsprodukterne, i- 35A reference electrode 11 is located outside the cell to prevent contamination with the reduction products, e.g.
DK 151904BDK 151904B
4 det den elektriske ledning foregår via en bro 12 omfattende en trevejsventil 13 og et rør 14, som er lukket med sintret glas, og som rager ned i katodefcammeret 2.4, the electrical conduit is conducted via a bridge 12 comprising a three-way valve 13 and a tube 14, which is closed with sintered glass, which projects into the cathode chamber 2.
Det efterfølgende eksempel tjener til illustration af 5 opfindelsen.The following example serves to illustrate the invention.
Eksempel.Example.
^ Den elektrokemiske reduktion af 2-(2-nitrovinyl)-thiophen foretages i en celle indeholdende en platinanode, og cellens ar-bejdselektrode eller katode er et kviksølvlag.The electrochemical reduction of 2- (2-nitrovinyl) thiophene is made in a cell containing a platinum anode and the working electrode or cathode of the cell is a mercury layer.
Reaktionsmediet er en eddikesyre-vand-blanding (50:50), og ^ 0,5 molær lithiumchlorid anvendes som elektrolyt.The reaction medium is an acetic acid-water mixture (50:50) and 0.5 molar lithium chloride is used as the electrolyte.
Reduktionspotentialet holdes ved 1,150 volt i forhold til en mættet kalomelelektrode, og reaktionen udføres ved stuetemperatur .The reduction potential is maintained at 1,150 volts relative to a saturated calomel electrode and the reaction is carried out at room temperature.
20 2-(2-nitrovinyl)-thiophensættes til det vandigt-organiske medium til en begyndelseskoncentration på 2,5 g/1.2- (2-Nitrovinyl) thiophenate is added to the aqueous-organic medium to an initial concentration of 2.5 g / L.
Cellen holdes under en nitrogenatmosfære, og reduktionen udføres under omrøring ved hjælp af strømgennemgang ved den forudbestemte spænding.The cell is kept under a nitrogen atmosphere and the reduction is carried out with stirring by means of current flow at the predetermined voltage.
Efter afslutning af elektrolysen (efter gennemgang af 2500 coulomb), neutraliseres katodekammerets elektrolyt, ekstra-heres med chloroform og vaskes derpå med vand samt tørres over vandfrit I^CO^. Den ønskede amin udvindes som hydrochlo= ridet eller oxalatet i ethanol.After completion of the electrolysis (after reviewing 2500 coulomb), the cathode chamber electrolyte is neutralized, extracted with chloroform and then washed with water and dried over anhydrous 1 CO 2. The desired amine is recovered as the hydrochloride or the oxalate in ethanol.
Udbyttet af 2-(2-aminoethyl)-thiophen er 47%, regnet i forhold 35 til udgangsmaterialet Dette udbytte svarer også til det fara-diske udbytte, eftersom den elektricitetsmængde, som er passeret gennem cellen, svarer til en 100% omdannelse.The yield of 2- (2-aminoethyl) thiophene is 47%, calculated in relation to the starting material. This yield also corresponds to the hazardous yield since the amount of electricity passed through the cell corresponds to a 100% conversion.
Claims (6)
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 |
|---|---|
| DK13879A DK13879A (en) | 1979-07-26 |
| DK151904B true DK151904B (en) | 1988-01-11 |
| DK151904C DK151904C (en) | 1988-06-06 |
Family
ID=9203795
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK013879A DK151904C (en) | 1978-01-25 | 1979-01-12 | METHOD OF ELECTROCHEMICAL 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 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
- 1979-01-24 BE BE0/193053A patent/BE873677A/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 |
|---|---|
| DE2960070D1 (en) | 1981-02-12 |
| IE790112L (en) | 1979-07-25 |
| ES476659A1 (en) | 1979-05-16 |
| JPS6046190B2 (en) | 1985-10-15 |
| FI62684C (en) | 1983-02-10 |
| GR65325B (en) | 1980-08-11 |
| DK13879A (en) | 1979-07-26 |
| NO790231L (en) | 1979-07-26 |
| FR2415671A1 (en) | 1979-08-24 |
| GB2013196B (en) | 1982-06-23 |
| DK151904C (en) | 1988-06-06 |
| ATA38379A (en) | 1981-04-15 |
| AT364839B (en) | 1981-11-25 |
| LU80772A1 (en) | 1979-05-16 |
| JPS54117462A (en) | 1979-09-12 |
| AR220736A1 (en) | 1980-11-28 |
| CH635618A5 (en) | 1983-04-15 |
| PT69105A (en) | 1979-02-01 |
| NO151715C (en) | 1985-05-22 |
| EP0003446B1 (en) | 1980-11-26 |
| GB2013196A (en) | 1979-08-08 |
| FR2415671B1 (en) | 1981-11-20 |
| FI790121A7 (en) | 1979-07-26 |
| BE873677A (en) | 1979-07-24 |
| IE47783B1 (en) | 1984-06-13 |
| FI62684B (en) | 1982-10-29 |
| MX5460E (en) | 1983-08-11 |
| EP0003446A1 (en) | 1979-08-08 |
| IT7947735A0 (en) | 1979-01-23 |
| IT1115135B (en) | 1986-02-03 |
| NO151715B (en) | 1985-02-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PBP | Patent lapsed |