CH94983A - 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
CH94983A
CH94983A CH94983DA CH94983A CH 94983 A CH94983 A CH 94983A CH 94983D A CH94983D A CH 94983DA CH 94983 A CH94983 A CH 94983A
Authority
CH
Switzerland
Prior art keywords
benzoic acid
production
ester
urethane derivative
urethane
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 CH94983A publication Critical patent/CH94983A/en

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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 einem       Ur-etharrderivatderBenzoesäur-e    gelangen kann,  wenn man     p-Aminobenzoesäureamylester    mit       Chlorkohlensäureglycolchlorhydrinester    um  setzt und den entstehenden     p-Chloruretharr-          benzoesäureamylester    mit     Diaethylamin    um  setzt.  



  Der so gebildete     w-Diaethylaminourethan-          p-benzoesäureamylester    schmilzt bei zirka 40  .  Das Chlorhydrat bildet bei 138-139   schmel  zende, in Wasser und Alkohol lösliche, in  Äther unlösliche Kristalle.         Beispiel     374 g     p-Aminoberrzoesäureamylester    wer  den in<B>1000</B> ccm Benzol gelöst und mit 142 g       Chlorlzohlensäureglycolchlorhydrinester    unter  Umrühren und Abkühlen mit Wasser versetzt.

    Nach beendigter Reaktion erwärmt man eine  halbe Stunde am Wasserbad und filtriert heiss  vom ausgeschiedenen     Aminobenzoesäureester-          chlorhydrat    ab und lässt den gebildeten     Chlor-          urethan        benzoes        äureamylester    au     skristallisieren.       Derselbe wird mit molekularen Mengen     Di-          äthylamin    in alkoholischer Lösung umgesetzt.  



  Der so erhaltene     Diaethylaminourethan-          benzoesäureamylester    wird durch Auflösen in  verdünnter Salzsäure und Fällen mit Soda  gereinigt. Das Chlorhydrat wird erhalten durch  Auflösen 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 a urethane derivative of benzoic acid can be obtained if p-aminobenzoic acid amyl ester is reacted with chlorocarbonic acid glycol chlorohydrin ester and the resulting p-chloro uretharine benzoic acid amyl ester is reacted with diaethylamine.



  The w-diaethylaminourethane-p-benzoic acid amyl ester formed in this way melts at about 40. At 138-139, the chlorohydrate forms melting crystals that are soluble in water and alcohol and insoluble in ether. EXAMPLE 374 g of amyl p-aminoberzoate were dissolved in 1000 cc of benzene and 142 g of glycol chlorohydrin ester were added while stirring and cooling with water.

    After the reaction has ended, the mixture is heated for half an hour on a water bath and the aminobenzoic acid ester chlorohydrate which has separated out is filtered off while the amyl chloro urethane benzoate formed is allowed to crystallize out. The same is reacted with molecular amounts of diethylamine in alcoholic solution.



  The amyl diaethylaminourethane benzoate obtained in this way 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,@ dass man p-Aminobenzoesäureamyl- ester mit Chlorkohlensäureglycolchlorhydrin- ester umsetzt und den entstehenden p-Chlor- urethanbenzoesäureamylester mit Diaethyl- amin umsetzt. PATENT CLAIM: Process for the production of a urethane derivative of benzoic acid, characterized in that p-aminobenzoic acid amyl ester is reacted with chlorocarbonic acid glycol chlorohydrin ester and the resulting p-chloro urethane benzoic acid amyl ester is reacted with di-ethylamine. Der so gebildete w-Diaethylaminourethan- p-benzoesäureamylester schmilzt bei zirka 40 . Das Chlorhydrat bildet bei 138-139 schmel zende, in Wasser und Alkohol lösliche, in Äther unlösliche Kristalle. The w-diaethylaminourethane-p-benzoic acid amyl ester formed in this way melts at about 40. At 138-139, the chlorohydrate forms melting crystals that are soluble in water and alcohol and insoluble in ether.
CH94983D 1921-10-14 1921-10-14 Process for the production of a urethane derivative of benzoic acid. CH94983A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH94568T 1921-10-14
CH94983T 1921-10-14

Publications (1)

Publication Number Publication Date
CH94983A true CH94983A (en) 1922-06-01

Family

ID=25704842

Family Applications (1)

Application Number Title Priority Date Filing Date
CH94983D CH94983A (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) CH94983A (en)

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