CH94569A - Process for the production of a urethane derivative of benzoic acid. - Google Patents

Process for the production of a urethane derivative of benzoic acid.

Info

Publication number
CH94569A
CH94569A CH94569DA CH94569A CH 94569 A CH94569 A CH 94569A CH 94569D A CH94569D A CH 94569DA CH 94569 A CH94569 A CH 94569A
Authority
CH
Switzerland
Prior art keywords
benzoic acid
production
urethane derivative
benzene
ethyl
Prior art date
Application number
Other languages
German (de)
Inventor
Gesellschaft Fuer Chemis Basel
Original Assignee
Chem Ind Basel
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 Chem Ind Basel filed Critical Chem Ind Basel
Publication of CH94569A publication Critical patent/CH94569A/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

  

  Verfahren zur Herstellung eines     Urethanderivates    der     Benzoesäure.       Es wurde gefunden, dass man zu dem  im Hauptpatent Nr. 93436 beschriebenen       co    -     Diäthylaminourethan    - p -     benzoesäureäthyl-          ester    auch gelangen kann, wenn man     p-          Anrinoberrzoesäureäthylester    mit     Phosgen    be  handelt und an die entstehende     Isoeyanatver-          bindung        Diäthylaminoäthanol    anlagert.  



       Beispiel:   <I>.</I>  



  Eine Lösung von<B>150</B>     gr        p-Arninoberrzoe-          säureäthylester    in 300 ccm trockenem Benzol  wird langsam unter Rühren und Abkühlen  zu einer Lösung von 50     gr        Phosgen    in 700 ccm  trockenem Benzol gegeben. Die Temperatur  soll bis zum Ende der Reaktion 40   nicht  überschreiten. Das Gemisch wird noch warm       abgenutscht    und der Rückstand von     p-Amino-          benzoesäureäthylester-chlorhydrat    mit Benzol  gewaschen. Die     Benzollösung    wird auf dem  Wasserbade zur Trockne eingedampft.

   Der  Rückstand besteht aus     Phenylisoeyanat-p-          carbonsäureäthylester.    Derselbe stellt geruch-    lose, in Benzol und Äther lösliche; bei ca. 60    schmelzende Kristalle dar.  



  Zu 1     Mol.    obiger     Isocyanat-Verbindung,     in wenig Benzol gelöst; wird 1     Mol.        Diäthyl-          aminoäthanol    gefügt.     DieReaktion        setztaugen-          blicklich    energisch ein.  



  Der so erhaltene     m-Diäthylaminourethan-p-          benzoesäureäthylester    wird durch Auflösen in  verdünnter Salzsäure und Fällen mit Soda  gereinigt.  



  Das Chlorhydrat wird erhalten durch Auf  lösen der Base in absolutem Alkohol und  Versetzen mit alkoholischer Salzsäure.



  Process for the production of a urethane derivative of benzoic acid. It has been found that the co-diethylaminourethane-p-benzoic acid ethyl ester described in the main patent no. 93436 can also be obtained if ethyl p-anrinoberzoate is treated with phosgene and diethylaminoethanol is added to the isoeyanate compound.



       Example: <I>. </I>



  A solution of 150 g of ethyl p-aminoberzoic acid in 300 cc of dry benzene is slowly added to a solution of 50 g of phosgene in 700 cc of dry benzene while stirring and cooling. The temperature should not exceed 40 until the end of the reaction. The mixture is suction filtered while it is still warm and the residue of ethyl p-aminobenzoate chlorohydrate is washed with benzene. The benzene solution is evaporated to dryness on the water bath.

   The residue consists of phenyl isoeyanate-p-carboxylic acid ethyl ester. It is odorless, soluble in benzene and ether; at approx. 60 melting crystals.



  To 1 mole of the above isocyanate compound, dissolved in a little benzene; 1 mol. Diethylaminoethanol is added. The reaction immediately sets in vigorously.



  The m-diethylaminourethane-p-benzoic acid ethyl ester thus obtained is purified by dissolving it in dilute hydrochloric acid and precipitating it with soda.



  The chlorine hydrate is obtained by dissolving the base in absolute alcohol and adding alcoholic hydrochloric acid.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines Urethan- derivates der Benzoesäure, dadurch gekenn zeichnet, däss man p -Aminobenzoe - säure- äthylester mit Phosgen behandelt und an die entstehende Isocyanatverbindung Diäthyl- aminoäthanol anlagert. PATENT CLAIM: Process for the production of a urethane derivative of benzoic acid, characterized in that ethyl p-aminobenzoate is treated with phosgene and diethylaminoethanol is added to the isocyanate compound formed.
CH94569D 1921-10-14 1921-10-14 Process for the production of a urethane derivative of benzoic acid. CH94569A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH94569T 1921-10-14

Publications (1)

Publication Number Publication Date
CH94569A true CH94569A (en) 1922-05-01

Family

ID=4352193

Family Applications (1)

Application Number Title Priority Date Filing Date
CH94569D CH94569A (en) 1921-10-14 1921-10-14 Process for the production of a urethane derivative of benzoic acid.

Country Status (1)

Country Link
CH (1) CH94569A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE895899C (en) * 1944-07-26 1953-11-09 Hoechst Ag Process for the production of dichlorocarbonic acid esters

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE895899C (en) * 1944-07-26 1953-11-09 Hoechst Ag Process for the production of dichlorocarbonic acid esters

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