CH235939A - Process for the preparation of a furancarboxamide. - Google Patents

Process for the preparation of a furancarboxamide.

Info

Publication number
CH235939A
CH235939A CH235939DA CH235939A CH 235939 A CH235939 A CH 235939A CH 235939D A CH235939D A CH 235939DA CH 235939 A CH235939 A CH 235939A
Authority
CH
Switzerland
Prior art keywords
sep
furan
dimethyl
preparation
furancarboxamide
Prior art date
Application number
Other languages
German (de)
Inventor
Ag J R Geigy
Original Assignee
Ag J R Geigy
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Ag J R Geigy filed Critical Ag J R Geigy
Publication of CH235939A publication Critical patent/CH235939A/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Furan Compounds (AREA)

Description

  

  Verfahren zur Herstellung eines     Furanearbonsäureamides.       Gegenstand vorliegenden     Zusatzpatentes     ist ein Verfahren zur Herstellung eines       Furancarbonsäuream2des.    Das Verfahren ist       daduroli        gekennzeichnet,    dass man     Diäthyl-          amin    auf eine     Verbindung    der Formel  
EMI0001.0009     
  
EMI0001.0010     
  
    worin <SEP> R <SEP> .reaktionsfähige, <SEP> sich <SEP> bei <SEP> der <SEP> Reak  tion, <SEP> abspaltende <SEP> Reste <SEP> bedeutet, <SEP> einwirken
<tb>  lässt. <SEP> Das <SEP> entstandene <SEP> 2,5-Dimethyl-furan  3,4-@dicarboinsäure-bis-,diäthyl:

  amid <SEP> siedet <SEP> bei
<tb>  0,4 <SEP> mm <SEP> bei <SEP> 154-156 . <SEP> Aus <SEP> Petroläther <SEP> bildet
<tb>  .es <SEP> grosse <SEP> ,dure@chsicbitige <SEP> Kristalle <SEP> vom <SEP> -Schmelz  punkt <SEP> 62 . <SEP> Es <SEP> ist <SEP> klar <SEP> wass <SEP> @erlö-slch.
<tb>  



  Vorteilhaft <SEP> kann <SEP> die <SEP> Reaktion <SEP> in <SEP> Gegen  wart <SEP> eines <SEP> Lösungsmittels <SEP> ausgeführt <SEP> werden.
<tb>  Die <SEP> neue <SEP> Verbindung <SEP> soll <SEP> als <SEP> Arznei  mittel <SEP> Verwendung <SEP> finden.
<tb>  



  <I>Beispiel:</I>
<tb>  18 <SEP> Teile <SEP> 2,5-I)imethyl:-furan-3,4-dicarbon  säurechlorid <SEP> (Kp." <SEP> 135-137 ), <SEP> dargestellt     
EMI0001.0011     
  
    aus <SEP> 2,5 <SEP> - <SEP> Dimethyl <SEP> - <SEP> furau <SEP> - <SEP> 3,4 <SEP> - <SEP> @d2carbonsäuxe
<tb>  und <SEP> Thionylchlorid, <SEP> werden <SEP> in <SEP> absolutem
<tb>  Äther <SEP> gelöst <SEP> unü <SEP> mit <SEP> 24 <SEP> Teilen <SEP> Diäthylami.n
<tb>  versetzt. <SEP> Sogleich:

   <SEP> sich <SEP> - <SEP> Diäthylamineblor  hydxyat <SEP> aus. <SEP> Nach <SEP> zweistündigem <SEP> Stehen <SEP> wird
<tb>  dieses <SEP> abgesaug <SEP> b, <SEP> der <SEP> Äther <SEP> mit
<tb>  Pottaschelösung <SEP> gewaschen, <SEP> dann <SEP> mit <SEP> Kalium  hydTogyd <SEP> get@,ocknet <SEP> und <SEP> verdampft. <SEP> Der
<tb>  Rücksitand,t <SEP> das <SEP> 2,5-Dimethyl-iurän-3,4-,di  carbousäuTe-bis,-@diäthylamd, <SEP> siedet <SEP> bei <SEP> 154
<tb>  bis <SEP> 156  <SEP> bei <SEP> 0,4 <SEP> mm. <SEP> Aus <SEP> Petroläther <SEP> bildet <SEP> es
<tb>  grosse <SEP> :durchsichtge <SEP> Kristalle <SEP> vom <SEP> Schmelz  punkt <SEP> 62 . <SEP> Es <SEP> ist <SEP> klar <SEP> und <SEP> wasserlöss#lich.



  Process for the preparation of a furanic acid amide. The subject of the present additional patent is a process for the production of a furancarboxylic acid amide. The method is characterized by daduroli that you diethylamine to a compound of the formula
EMI0001.0009
  
EMI0001.0010
  
    where <SEP> R <SEP> .reactive, <SEP> means <SEP> with <SEP> the <SEP> reaction, <SEP> means separating <SEP> residues <SEP>, <SEP> act
<tb> lets. <SEP> The <SEP> resulting <SEP> 2,5-dimethyl-furan 3,4- @ dicarboic acid-bis-, diethyl:

  amid <SEP> boils with <SEP>
<tb> 0.4 <SEP> mm <SEP> with <SEP> 154-156. <SEP> Forms <SEP> from <SEP> petroleum ether <SEP>
<tb> .es <SEP> large <SEP>, dure @ chsicbitige <SEP> crystals <SEP> from the <SEP> melting point <SEP> 62. <SEP> It <SEP> is <SEP> clear <SEP> what <SEP> @ extinguishes.
<tb>



  Advantageously, <SEP> <SEP> the <SEP> reaction <SEP> can be carried out <SEP> in <SEP> presence <SEP> of a <SEP> solvent <SEP>.
<tb> The <SEP> new <SEP> connection <SEP> should be used <SEP> as a <SEP> medicinal product <SEP> <SEP>.
<tb>



  <I> Example: </I>
<tb> 18 <SEP> parts <SEP> 2,5-I) imethyl: -furan-3,4-dicarboxylic acid chloride <SEP> (cp. "<SEP> 135-137), <SEP> shown
EMI0001.0011
  
    made of <SEP> 2,5 <SEP> - <SEP> Dimethyl <SEP> - <SEP> furau <SEP> - <SEP> 3,4 <SEP> - <SEP> @ d2carbonsäuxe
<tb> and <SEP> thionyl chloride, <SEP> become <SEP> in <SEP> absolute
<tb> ether <SEP> dissolved <SEP> unü <SEP> with <SEP> 24 <SEP> parts <SEP> diethylami.n
<tb> offset. <SEP> Immediately:

   <SEP> <SEP> - <SEP> diethylamine blorohydxyate <SEP>. <SEP> After standing <SEP> for two hours, <SEP> will be
<tb> this <SEP> sucked <SEP> b, <SEP> the <SEP> ether <SEP> with
<tb> Potash solution <SEP> washed, <SEP> then <SEP> with <SEP> potassium hydTogyd <SEP> get @, ocknet <SEP> and <SEP> evaporated. <SEP> The
<tb> Returns, t <SEP> the <SEP> 2,5-dimethyl-iurän-3,4-, di carbousäuTe-bis, - @ diethylamd, <SEP> boils <SEP> at <SEP> 154
<tb> to <SEP> 156 <SEP> at <SEP> 0.4 <SEP> mm. <SEP> <SEP> forms it from <SEP> petroleum ether <SEP>
<tb> large <SEP>: transparent <SEP> crystals <SEP> from the <SEP> melting point <SEP> 62. <SEP> It <SEP> is <SEP> clear <SEP> and <SEP> water-soluble.

Claims (1)

PATENTANSPRUCH: EMI0001.0012 Verfahren <SEP> zur <SEP> Herstellung <SEP> eines <SEP> Furan carbonsäurreamides@, <SEP> dadurch <SEP> gekennzeichnet, <tb> dass <SEP> ,man: <SEP> Diäthyl:amin <SEP> auf <SEP> eine <SEP> Verbindung <tb> der <SEP> Formel EMI0001.0013 EMI0002.0001 worin <SEP> P. <SEP> .reaktionsfällige, <SEP> sich <SEP> bei <SEP> der <SEP> Reak tion <SEP> abspaltende <SEP> Reste <SEP> bedeutet, <SEP> einwirken <tb> lässt. <SEP> Das <SEP> entstandene <SEP> 2,5-Dimethyl-furan 3,,4-diearb@onsäuT,e@bis-,diäthylamid <SEP> siedet <SEP> bei <tb> 0,4 <SEP> mm <SEP> bei <SEP> 154--156 .- <SEP> Aus <SEP> Petroläthe.r <SEP> bildlet es grosse :durchsichtige Kristalle vom Schmelz punkt 62 . PATENT CLAIM: EMI0001.0012 Process <SEP> for <SEP> production <SEP> of a <SEP> furan carboxylic acid reamide @, <SEP> marked with <SEP>, <tb> that <SEP>, man: <SEP> diethyl: amine <SEP> on <SEP> a <SEP> connection <tb> of the <SEP> formula EMI0001.0013 EMI0002.0001 where <SEP> P. <SEP> .reactive, <SEP> means <SEP> with <SEP> the <SEP> reaction <SEP> separating <SEP> residues <SEP>, <SEP> act <tb> lets. <SEP> The <SEP> resulting <SEP> 2,5-dimethyl-furan 3,, 4-diearb @ onsäuT, e @ bis-, diethylamide <SEP> boils with <SEP> <tb> 0.4 <SEP> mm <SEP> at <SEP> 154--156 .- <SEP> From <SEP> petroleum ether.r <SEP> it forms large: transparent crystals with a melting point of 62. Es ist klar wasserlöslich. Die neue Verbindung soll als Arznei mittel Verwendung finden. It is clearly soluble in water. The new compound is to be used as a medicinal product.
CH235939D 1939-12-02 1939-12-02 Process for the preparation of a furancarboxamide. CH235939A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH235939T 1939-12-02
CH226786T 1939-12-02

Publications (1)

Publication Number Publication Date
CH235939A true CH235939A (en) 1944-12-31

Family

ID=25727031

Family Applications (1)

Application Number Title Priority Date Filing Date
CH235939D CH235939A (en) 1939-12-02 1939-12-02 Process for the preparation of a furancarboxamide.

Country Status (1)

Country Link
CH (1) CH235939A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2745845A (en) * 1950-06-30 1956-05-15 Lilly Co Eli 1-formyl-2-dialkoxymethyl-succinic acid esters and their cyclization to heterocyclic compounds

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2745845A (en) * 1950-06-30 1956-05-15 Lilly Co Eli 1-formyl-2-dialkoxymethyl-succinic acid esters and their cyclization to heterocyclic compounds

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