CH94984A - 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
CH94984A
CH94984A CH94984DA CH94984A CH 94984 A CH94984 A CH 94984A CH 94984D A CH94984D A CH 94984DA CH 94984 A CH94984 A CH 94984A
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 CH94984A publication Critical patent/CH94984A/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     Ürethanderivates    der     Benzoesäure.       Es Wurde gefunden, dass man zu einem       UrethanderivatderBenzoesäure    gelangen kann,  wenn man     p-Aminobenzoesäureäthylester    mit       Phosgen    behandelt und an die entstehende       Isocyanatverbindung        Dimethylaminoaethanol     anlagert. Der so entstehende     m-Diinethyl-          aminourethan-p-benzoesäureäthylester    bildet  ein in Wasser leicht lösliches kristallinisches  Chlorhydrat vom Schmelzpunkt 224-225  .

         Beispiel     Eine Lösung von 150 g     p-Aminobenzoe-          säureäthylester    in 300 ccm trockenem Benzol  wird langsam unter Rühren und Abkühlen  zu einer Lösung von 50 g     Phosgen    in 700       ccm    trockenem Benzol gegeben. Die Tem  peratur soll bis zum Ende der Reaktion 400  nicht überschreiten. Das Gemisch wird. noch  warm     abgenutscht    und der Rückstand von       p-Aminobenzoesäureäthylesterchlorhydrat    mit  Benzol gewaschen. Die     Benzollösung    wird auf  dein Wasserbade zur Trockne eingedampft.

    Der Rückstand besteht aus     Phenylisocyanat-          p-carbonsäureäthylester.    Derselbe stellt ge  ruchlose, in Benzol und Äther lösliche, bei  zirka<B>600</B> schmelzende Kristalle dar.    Zu 1     Mol.    obiger     Isocyanatverbindung,    in  wenig Benzol gelöst, wird 1     1K1.        Dimethyl-          aminoaethanol    gefügt. Die Reaktion setzt  augenblicklich energisch ein.  



       U,    Der so erhaltene     w-Dimethylaminourethan-          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 a urethane derivative of benzoic acid can be obtained if ethyl p-aminobenzoate is treated with phosgene and the resulting isocyanate compound dimethylaminoethanol is added. The resulting m-Diinethylaminourethan-p-Benzoäureäthylester forms a crystalline hydrochloride which is easily soluble in water and has a melting point of 224-225.

         EXAMPLE A solution of 150 g of ethyl p-aminobenzoate in 300 cc of dry benzene is slowly added with stirring and cooling to a solution of 50 g of phosgene in 700 cc of dry benzene. The temperature should not exceed 400 by the end of the reaction. The mixture will. Sucked off while still warm and washed the residue of ethyl p-aminobenzoate with benzene. The benzene solution is evaporated to dryness on your water bath.

    The residue consists of phenyl isocyanate-p-carboxylic acid ethyl ester. It represents odorless crystals, soluble in benzene and ether, melting at about 600. To 1 mol of the above isocyanate compound, dissolved in a little benzene, 1 1K1 is added. Dimethylamino ethanol added. The reaction sets in immediately and vigorously.



       U, The w-dimethylaminourethane-p-benzoic acid ethyl ester obtained in this way is purified by dissolving it in dilute hydrochloric acid and precipitating it with soda. .



  The chlorohydrate is obtained through. Dissolve the base in absolute alcohol and add alcoholic hydrochloric acid.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines Urethan- derivates der Benzoesäure, dadurch gekenn zeichnet, dass man p-Aminobenzoesäureäthyl- ester mit Phosgen behandelt und an die ent stehende Isocyanatverbindung Dimethylamino- aethanol 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 added to the isocyanate compound dimethylaminoethanol. Der so entstehende cv-Di- methylamin our ethan - p - benzoesäureäthylester bildet ein in Wasser leicht lösliches, kristal linisches Chlorhydrat vom Schmelzpunkt 224-2250. The resulting cv-dimethylamine our ethane - p - benzoic acid ethyl ester forms a crystalline hydrochloric acid which is easily soluble in water and has a melting point of 224-2250.
CH94984D 1921-10-14 1921-10-14 Process for the production of a urethane derivative of benzoic acid. CH94984A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH94984T 1921-10-14
CH94569T 1921-10-14

Publications (1)

Publication Number Publication Date
CH94984A true CH94984A (en) 1922-06-01

Family

ID=25704843

Family Applications (1)

Application Number Title Priority Date Filing Date
CH94984D CH94984A (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) CH94984A (en)

Cited By (2)

* 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
DE943407C (en) * 1953-01-24 1956-05-17 Bayer Ag Process for the preparation of isocyanate carboxylic acid chlorides

Cited By (2)

* 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
DE943407C (en) * 1953-01-24 1956-05-17 Bayer Ag Process for the preparation of isocyanate carboxylic acid chlorides

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