CH302372A - Process for the preparation of a new acetoacetylamino compound. - Google Patents

Process for the preparation of a new acetoacetylamino compound.

Info

Publication number
CH302372A
CH302372A CH302372DA CH302372A CH 302372 A CH302372 A CH 302372A CH 302372D A CH302372D A CH 302372DA CH 302372 A CH302372 A CH 302372A
Authority
CH
Switzerland
Prior art keywords
compound
new
acetic acid
acetoacetylamino
preparation
Prior art date
Application number
Other languages
German (de)
Inventor
Ag Durand Huguenin
Original Assignee
Durand & Huguenin 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 Durand & Huguenin Ag filed Critical Durand & Huguenin Ag
Publication of CH302372A publication Critical patent/CH302372A/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/22—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with hetero atoms directly attached to ring nitrogen atoms
    • C07D295/26—Sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings 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
    • C07D277/38—Nitrogen atoms

Landscapes

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

Description

  

  verfahren zur Herstellung einer neuen     Acetoacetylaminoverbindung.       Gegenstand der     vorliegenden    Erfindung  ist ein Verfahren zur     Herstellung    einer neuen       Acetoacetylaminoverbindung,    nämlich des 1       Ac(@toacetv1aniinobenzo#l-4-sulfonsäuremorph-.)-          lids,    und ist dadurch     gekennzeichnet,        dass     man     1-Aminobenzol-4-sulfonsäureinorpholid    in  90- bis 100prozentiger Essigsäure bei einer  Temperatur zwischen. 40 und 80  C mit     Di-          keten    umsetzt.  



  Diese Verbindung ist ein weisser, kristalli  ner Körper vom     Schmelzpunkt    1.4? bis 144  C,       der    in Wasser     u-nlöslieh,    jedoch in Eisessig,  Benzol und Alkohol. löslich ist.  



  Die so erhaltene Verbindung     l:ässt    sich mit  den verschiedenartigsten     Diazoverbindungen     leicht kuppeln und ist somit ein wertvolles       Zwischenprodukt    für die Herstellung von  neuen     Azofarbstoffen.     



  Die Umsetzung mit     Diketen    erfolgt vor  zugsweise bei einer Temperatur von 60 bis  <B>70"</B> C und in     r        egenwa.rt    von Eisessig.         Beispiel:       36,5 Teile     1-Aminobenzol-4-sulfonsäuremor-          pholid    werden in 450 Teilen Eisessig suspen  diert. In die Suspension werden im Verlaufe       voii        11/2    Stunden bei     6'5     C     1-1,5    Teile     Diketen            zutropfen    gelassen, wobei die suspendierte  Verbindung langsam in Lösung geht.

   Es wird  dann noch während 4     Stunden    bei dieser     T'ein-          peratur    weiter gerührt, worauf nach Klären  der     Lösung    das Reaktionsprodukt durch Ab  destillieren des Eisessigs im Vakuum isoliert  wird (Ausbeute 83 %).



  process for the preparation of a new acetoacetylamino compound. The present invention relates to a process for the preparation of a new acetoacetylamino compound, namely 1 Ac (@ toacetv1aniinobenzo # l-4-sulfonic acid morph -.) - lids, and is characterized in that 1-aminobenzene-4-sulfonic acid inorpholide in 90 to 100% acetic acid at a temperature between. 40 and 80 C with dictates.



  This compound is a white, crystalline body with a melting point of 1.4? up to 144 C, which is insoluble in water, but in glacial acetic acid, benzene and alcohol. is soluble.



  The compound obtained in this way can easily be coupled with the most varied of diazo compounds and is thus a valuable intermediate product for the production of new azo dyes.



  The reaction with diketene is preferably carried out at a temperature of 60 to 70 ° C. and in the presence of glacial acetic acid Parts of glacial acetic acid are suspended in the course of 11/2 hours at 6.5 ° C. 1-1.5 parts of diketene are added dropwise, the suspended compound slowly dissolving.

   Stirring is then continued for 4 hours at this temperature, whereupon, after the solution has been clarified, the reaction product is isolated by distilling off the glacial acetic acid in vacuo (yield 83%).

Claims (1)

PATENTANSPRUCH Verfahren zur Herstellung einer neuen N-Acetoacety laminoverbindung, dadurch ge kennzeichnet, dass man 1-Aminobenzol-4-sul- fonsäuremorpholid in 90- bis 100prozentiger Essigsäure bei einer Temperatur zwischen 40 und 80 C mit Diketen umsetzt. Diese Verbindung ist, ein weisser, kristalli ner Körper vom Schmelzpunkt 142- bis 144 C, der in Wasser unlöslich, jedoch in Eisessig, Benzol und Alkohol löslich ist. UNTERANSPRÜCHE 1. PATENT CLAIM Process for the production of a new N-acetoacety laminoverbindungen, characterized in that 1-aminobenzene-4-sulphonic acid morpholide is reacted with diketene in 90 to 100 percent acetic acid at a temperature between 40 and 80 C. This compound is a white, crystalline body with a melting point of 142 to 144 C, which is insoluble in water, but soluble in glacial acetic acid, benzene and alcohol. SUBCLAIMS 1. Verfahren naeh Patentanspruch, da durch gekennzeichnet, dass die Umsetzung in Eisessig durchgeführt wird. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass die Umsetzung bei 60 bis 70 C durchgeführt wird. Method according to patent claim, characterized in that the reaction is carried out in glacial acetic acid. Process according to patent claim, characterized in that the reaction is carried out at 60 to 70 ° C.
CH302372D 1951-08-21 1951-08-21 Process for the preparation of a new acetoacetylamino compound. CH302372A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH302372T 1951-08-21
CH299706T 1951-08-21

Publications (1)

Publication Number Publication Date
CH302372A true CH302372A (en) 1954-10-15

Family

ID=25734087

Family Applications (1)

Application Number Title Priority Date Filing Date
CH302372D CH302372A (en) 1951-08-21 1951-08-21 Process for the preparation of a new acetoacetylamino compound.

Country Status (1)

Country Link
CH (1) CH302372A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2553414A1 (en) * 1983-10-18 1985-04-19 Choay Sa NOVEL N-CYCLIC BENZENESULFONAMIDES, PROCESS FOR THEIR PREPARATION AND THEIR USE AS ACTIVE SUBSTANCES OF PHARMACEUTICAL COMPOSITIONS
US4871843A (en) * 1983-10-18 1989-10-03 Dropic-Societe Civile De Gestion De Droits De Propriete Industrielle Cyclic benzenesulfonamides, process for their preparation and their use as active substance of pharmaceutical compositions
EP0685470A3 (en) * 1994-06-01 1996-02-07 Kureha Chemical Ind Co Ltd Benzene derivatives and pharmaceutical composition.

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2553414A1 (en) * 1983-10-18 1985-04-19 Choay Sa NOVEL N-CYCLIC BENZENESULFONAMIDES, PROCESS FOR THEIR PREPARATION AND THEIR USE AS ACTIVE SUBSTANCES OF PHARMACEUTICAL COMPOSITIONS
US4760062A (en) * 1983-10-18 1988-07-26 Dropic, Societe Civile De Gestion De Droits De Propriete Industrielle Pharmaceutical compositions of N-heterocyclic benzenesulfonamides and their use
US4871843A (en) * 1983-10-18 1989-10-03 Dropic-Societe Civile De Gestion De Droits De Propriete Industrielle Cyclic benzenesulfonamides, process for their preparation and their use as active substance of pharmaceutical compositions
EP0685470A3 (en) * 1994-06-01 1996-02-07 Kureha Chemical Ind Co Ltd Benzene derivatives and pharmaceutical composition.
US5696118A (en) * 1994-06-01 1997-12-09 Kureha Chemical Industry Co., Ltd. Benzene derivatives and pharmaceutical composition
US5731310A (en) * 1994-06-01 1998-03-24 Kureha Chemical Industry Co., Ltd. Benzene derivatives and pharmaceutical composition
US5739131A (en) * 1994-06-01 1998-04-14 Kureha Chemical Industry Co., Ltd. Benzene derivatives and pharmaceutical composition

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