CH217079A - Process for the preparation of a derivative of citrazinic acid. - Google Patents

Process for the preparation of a derivative of citrazinic acid.

Info

Publication number
CH217079A
CH217079A CH217079DA CH217079A CH 217079 A CH217079 A CH 217079A CH 217079D A CH217079D A CH 217079DA CH 217079 A CH217079 A CH 217079A
Authority
CH
Switzerland
Prior art keywords
derivative
acid
preparation
citrazinic acid
water
Prior art date
Application number
Other languages
German (de)
Inventor
Chemisches Industrielles Cilag
Original Assignee
Cilag Chemisches Ind Lab A G
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 Cilag Chemisches Ind Lab A G filed Critical Cilag Chemisches Ind Lab A G
Publication of CH217079A publication Critical patent/CH217079A/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
    • C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
    • C09B29/3604—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom
    • C09B29/3617—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom
    • C09B29/3621—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom from a pyridine ring
    • C09B29/3626—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom from a pyridine ring from a pyridine ring containing one or more hydroxyl groups (or = O)

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Description

       

  Verfahren zur Darstellung eines Abkömmlings der     Zitrazinsäure.       Die Erfindung betrifft ein Verfahren zur  Darstellung eines     neuen    Abkömmlings der       Zitrazinsäure.    Die neue Verbindung hat sich  als solche oder in Form ihrer Salze wertvoll  erwiesen für die Bekämpfung infektiöser,  vornehmlich durch Kokken verursachter Er  krankungen. Sie ist nicht     toxisch    und besitzt  eine grosse     Durchdringungsfähigkeit    des  lebenden Gewebes.

   Das Verfahren ist da  durch gekennzeichnet, dass     Zitrazinsäure    mit       diazotiertem        Sulfanilamid    gekuppelt wird,  wobei sich die     3-(4'-Sulfonamido-benzolazo-)          2,6-dioxy-pyridin-4-karbonsäure    bildet.  



  Zur Darstellung der neuen Verbindung  verfährt man     beispielsweise    folgendermassen:  35 g     p-Aminobenzolsulfonamid    werden  mit 52     cm@    33 %     iger    Salzsäure und 200 cm'  Wasser     angerührt    und in der     gälte    mit einer  konzentrierten Lösung von 15     g        Natrium-          nitrit        dia.zotiert.    Die     Diazoniumlösung        lässt     man unter Rühren in eine Lösung von 30 .g       Zitrazinsäure,

      40 g     Natriumkarbonat    und    10 g     Natriumazetat    in 150     cm@    Wasser -ein  fliessen, wobei die     3-(4'-Sulfonamido-benzol-          azo-)2,6-dioxy-pyridin-4-karbonsäure    in be  rechneter Menge als     Natriumsalz        ausfällt.     Die freie     Kaxbonsäure        wird    durch     Umfällen,     aus ihrer     alkalsohen    Lösung mit Säure er  halten.

   Sie ist gelborange,     schmilzt    bei<B>278'</B>  unter Zersetzung, ist wenig löslich in Al  kohol, nahezu unlöslich in Wasser, Azeton  und Benzol und bildet ein in Wasser bei  Zimmertemperatur zu<B>1,5%</B>     lösliches        Na-          triumsa1z.  



  Process for the preparation of a derivative of citrazinic acid. The invention relates to a method for preparing a new derivative of citrazinic acid. The new compound has proven to be valuable as such or in the form of its salts for combating infectious diseases mainly caused by cocci. It is non-toxic and has a great ability to penetrate living tissue.

   The process is characterized in that citrazinic acid is coupled with diazotized sulfanilamide, the 3- (4'-sulfonamido-benzene-azo) 2,6-dioxy-pyridine-4-carboxylic acid being formed.



  The procedure for preparing the new compound is as follows: 35 g of p-aminobenzenesulfonamide are mixed with 52 cm @ 33% hydrochloric acid and 200 cm 'of water and dia.zotiert with a concentrated solution of 15 g of sodium nitrite. The diazonium solution is allowed to stir into a solution of 30 g citrazinic acid,

      40 g of sodium carbonate and 10 g of sodium acetate in 150 cm @ of water flow -in, the 3- (4'-sulfonamido-benzene-azo) 2,6-dioxy-pyridine-4-carboxylic acid precipitating in a calculated amount as the sodium salt. The free kaxboxylic acid is obtained by reprecipitation from its alkaline solution with acid.

   It is yellow-orange, melts at <B> 278 '</B> with decomposition, is sparingly soluble in alcohol, almost insoluble in water, acetone and benzene and forms <B> 1.5% in water at room temperature </ B> soluble sodium salt.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung eines Abkömm lings der Zitrazinsäure, dadurch gekennzeich net, dass Zitrazinsäure mit diazotiertem Sulf- anilamid gekuppelt wird, wobei sich die 3-(4'- Sulfonamido-benzolazo-) 2,6-dioxy-pyridin-4- karbonsäure bildet. PATENT CLAIM: Process for the preparation of a derivative of citrazinic acid, characterized in that citrazinic acid is coupled with diazotized sulfanilamide, with 3- (4'-sulfonamido-benzolazo) 2,6-dioxy-pyridine-4-carboxylic acid forms. Das Verfahrensprodukt ist gelborange, schmilzt bei 278 unter Zersetzung, ist wenig löslich in Alkohol, nahezu unlöslich in Was ser, Azeton und Benzol und bildet ein in Wasser bei Zimmertemperatur zu 1,5 lösliches Natriumsalz. Es soll als solches oder in Form seiner Salze zur Bekämpfung infek- tiöser, insbesondere durch Kokken verur sachter Erkrankungen verwendet werden. The product of the process is yellow-orange, melts at 278 with decomposition, is sparingly soluble in alcohol, almost insoluble in water, acetone and benzene and forms a sodium salt which is 1.5% soluble in water at room temperature. It is intended to be used as such or in the form of its salts to combat infectious diseases, in particular diseases caused by cocci.
CH217079D 1940-05-15 1940-05-15 Process for the preparation of a derivative of citrazinic acid. CH217079A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH217079T 1940-05-15

Publications (1)

Publication Number Publication Date
CH217079A true CH217079A (en) 1941-09-30

Family

ID=4449933

Family Applications (1)

Application Number Title Priority Date Filing Date
CH217079D CH217079A (en) 1940-05-15 1940-05-15 Process for the preparation of a derivative of citrazinic acid.

Country Status (1)

Country Link
CH (1) CH217079A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2121748A1 (en) * 1971-01-14 1972-08-25 Ciba Geigy Ag

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2121748A1 (en) * 1971-01-14 1972-08-25 Ciba Geigy Ag

Similar Documents

Publication Publication Date Title
CH217079A (en) Process for the preparation of a derivative of citrazinic acid.
CH222727A (en) Process for the preparation of a derivative of citrazinic acid.
CH222728A (en) Process for the preparation of a derivative of citrazinic acid.
CH222729A (en) Process for the preparation of a derivative of citrazinic acid.
CH222730A (en) Process for the preparation of a derivative of citrazinic acid.
AT117855B (en) Process for the preparation of water-soluble secondary diazoamido compounds of the aromatic series.
CH99200A (en) Process for the preparation of an oil- and fat-soluble salt of an acridinium compound
CH185606A (en) Process for producing an azo compound.
CH265405A (en) Process for the preparation of a new monoazo dye.
CH215940A (en) Process for the preparation of an azo dye.
CH217973A (en) Process for the preparation of an azo dye.
CH213749A (en) Process for the preparation of 2-oxynaphthalene-4-sulfonic acid.
CH219580A (en) Process for the preparation of an azo dye.
CH218815A (en) Process for the preparation of a disazo dye.
CH206626A (en) Process for preparing a sulfonic acid amide compound.
CH189310A (en) Process for the preparation of a chromium-containing azo dye.
CH185344A (en) Process for the preparation of a metal-containing azo dye.
CH193081A (en) Process for the preparation of a new monoazo dye.
CH155326A (en) Process for the preparation of a water-soluble mixed aromatic-aliphatic diazoamino compound.
CH200997A (en) Process for the production of a new azo dye.
CH261274A (en) Process for the preparation of a new monoazo dye.
CH236354A (en) Process for the preparation of 2- (2&#39;-oxybenzoic acid- (5&#39;-azo-4 &#34;) -benzen-1&#34; -sulfonamido) -thiazole.
CH209085A (en) Process for the preparation of a water-soluble azo dye.
CH148341A (en) Process for the preparation of a water-soluble secondary diazoamino compound of aromatic series.
CH220110A (en) Process for the production of a new azo dye.