CH200907A - Process for the preparation of a nitrogen-containing aromatic aldehyde. - Google Patents

Process for the preparation of a nitrogen-containing aromatic aldehyde.

Info

Publication number
CH200907A
CH200907A CH200907DA CH200907A CH 200907 A CH200907 A CH 200907A CH 200907D A CH200907D A CH 200907DA CH 200907 A CH200907 A CH 200907A
Authority
CH
Switzerland
Prior art keywords
nitrogen
containing aromatic
aromatic aldehyde
preparation
aldehyde
Prior art date
Application number
Other languages
German (de)
Inventor
Aktiengesellsc Farbenindustrie
Original Assignee
Ig Farbenindustrie Ag
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 Ig Farbenindustrie Ag filed Critical Ig Farbenindustrie Ag
Publication of CH200907A publication Critical patent/CH200907A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings

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

Description

  

  Verfahren zur Herstellung eines     stickstoffhaltigen    aromatischen Aldehyds.         Gegenstand    des vorliegenden     Patentes    ist  ein Verfahren zur Herstellung     eines        stick-          stoffhaltigen    aromatischen     Aldehyds.        Das     Verfahren ist     dadurch        .gekennzeichnet,        dass:

       man     N-Di-chloräthyl-anilin,        N-Methylform-          anilid        und        Phosphoroxychlorid    aufeinander  einwirken lässt und .in dem so erhaltenen       p-Di-(chlorälhyl)-amino-benzaldehyd    durch  Behandlung mit einem verseifenden Mittel  das Chlor gegen eine Sauerstoffbrücke aus  tauscht. Der so     erhältliche        p-Morpholino-          benzaIdehyd        kristallisiert    in feinen farb  losen     Kristallen:    vom F.

   P.     6ss    bis<B>67'.</B> Er  soll zur     Synthese,    von Farbstoffen u. a. die  nen.  



  <I>Beispiel:</I>  Zu 169     Gewichtsteilen        Phosphoroxychlorid     gibt man bei<B>N</B>   allmählich 91 Gewichts  teile     N-Di-oxyäthyl=anilin    und -erwärmt das       Gemisch    noch.

       ,einige    Zeit auf 90     bis        10,0.'.     Nach dem Abkühlen lässt man bei 10     bis   <B>15'</B>  allmählich ein     Gemisch    von 135 Gewichts-    teilen     N-Methylformanilid    und 154     Gewichts-          teilen        Phosphoroxychlorid        zutropfen,    er  wärmt noch einige Stunden auf 45 bis<B>50'</B>  und trägt auf     Eis    aus.

   Der entstandene       p-Di-(chloräthyl)-aminobenzaldehyd    scheidet  sich als schwach :gefärbtes Öl ab,     welches     nach kurzem Rühren zu feinen,     praktisch     reinen     Kristallen    erstarrt.

   Der Aldehyd       kristallisiert    aus Alkohol in :derben langen       Prismen    vom Schmelzpunkt<B>88,5'.</B> Dieser       wird    mit etwa     ,der        15fachen    Menge     50%igem     Alkohol     und    1,05     Mol    :Soda unter Rühren  am     Rückflusskühler        gekocht.    mach     Abdastil-          lieren        des    Alkohole erhält man den     p-Mor-          pholinabenzal,dehyd    als :

  schwach     gefärbtes,    in  der     Kälte    zu     Kristallen        erstarrendes   <B>01.</B>  Durch     Umkristallisieren    aus sehr wenig  Alkohol erhält man :den     Ald-e & yd    in     feinen     farblosen Kristallen vom     Schmelzpunkt    66  bis 67  . Er ist     ausserordentlich        löslich    in  organischen Mitteln wie Alkohol,     Essigester,          Aceton,        Äther        usw.  



  Process for the preparation of a nitrogen-containing aromatic aldehyde. The present patent relates to a process for the production of a nitrogen-containing aromatic aldehyde. The procedure is characterized in that:

       N-dichloroethyl aniline, N-methylform anilide and phosphorus oxychloride are allowed to act on one another and the chlorine in the p-di (chloroethyl) amino benzaldehyde thus obtained is exchanged for an oxygen bridge by treatment with a saponifying agent. The p-morpholinobenzaldehyde that can be obtained in this way crystallizes in fine, colorless crystals: from F.

   P. 6ss to <B> 67 '. </B> It should be used for synthesis, dyes and the like. a. serve.



  <I> Example: </I> 91 parts by weight of N-dioxyethyl = aniline are gradually added to 169 parts by weight of phosphorus oxychloride at <B> N </B> and the mixture is warmed up.

       'For some time to 90 to 10.0.'. After cooling, a mixture of 135 parts by weight of N-methylformanilide and 154 parts by weight of phosphorus oxychloride is gradually added dropwise at 10 to 15 '; it is heated to 45 to 50' for a few hours / B> and carries out on ice.

   The resulting p-di- (chloroethyl) -aminobenzaldehyde separates out as a weakly colored oil, which solidifies to fine, practically pure crystals after brief stirring.

   The aldehyde crystallizes from alcohol in: coarse long prisms with a melting point of <B> 88.5 '. </B> This is boiled with about 15 times the amount of 50% alcohol and 1.05 mol: soda while stirring on the reflux condenser. When the alcohol is removed, the p-morpholinabenzal is obtained, dehydrogenated as:

  weakly colored <B> 01. </B> which solidifies into crystals in the cold. Recrystallization from very little alcohol gives: Ald-e & yd in fine colorless crystals with a melting point of 66 to 67. It is extremely soluble in organic agents such as alcohol, ethyl acetate, acetone, ether, etc.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines stick- stoffhaltigen aromatischen Aldehyds, da durch gekennzeichnet, dass man N-Di-chlor- ä,thyl-anilin, N-Methylformanilid und Phos- phoroxychlorid aufeinander einwirken lässt und in .dem so erhaltenen p-Di-(chloräthyl) PATENT CLAIM: Process for the production of a nitrogen-containing aromatic aldehyde, characterized in that N-di-chloro, thyl-aniline, N-methylformanilide and phosphorus oxychloride are allowed to act on one another and the p-di- (chloroethyl) - aminobenzaIdehyd das Chlor durch Behand- lung mit einem verseifenden Mittel gegen eine .Sauerstoffbrücke austauscht. Der so erhältliche p-Morpholinobenzaldehyd kri stallisiert in feinen farblosen Kristallen vom h. P. 66 bis 67 . - aminobenzene aldehyde which exchanges chlorine for an oxygen bridge by treatment with a saponifying agent. The thus obtainable p-morpholinobenzaldehyde crystallized in fine colorless crystals of the h. P. 66 to 67.
CH200907D 1935-04-12 1936-04-02 Process for the preparation of a nitrogen-containing aromatic aldehyde. CH200907A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE200907X 1935-04-12
CH192574T 1936-04-02

Publications (1)

Publication Number Publication Date
CH200907A true CH200907A (en) 1938-10-31

Family

ID=25722302

Family Applications (1)

Application Number Title Priority Date Filing Date
CH200907D CH200907A (en) 1935-04-12 1936-04-02 Process for the preparation of a nitrogen-containing aromatic aldehyde.

Country Status (1)

Country Link
CH (1) CH200907A (en)

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