CH253641A - Process for the preparation of 3,5-dibromo-salicoylamino-antipyrine. - Google Patents

Process for the preparation of 3,5-dibromo-salicoylamino-antipyrine.

Info

Publication number
CH253641A
CH253641A CH253641DA CH253641A CH 253641 A CH253641 A CH 253641A CH 253641D A CH253641D A CH 253641DA CH 253641 A CH253641 A CH 253641A
Authority
CH
Switzerland
Prior art keywords
antipyrine
dibromo
salicoylamino
preparation
amino
Prior art date
Application number
Other languages
German (de)
Inventor
Ag Sandoz
Original Assignee
Ag Sandoz
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 Ag Sandoz filed Critical Ag Sandoz
Publication of CH253641A publication Critical patent/CH253641A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole 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
    • C07D231/44—Oxygen and nitrogen or sulfur and nitrogen atoms
    • C07D231/46—Oxygen atom in position 3 or 5 and nitrogen atom in position 4
    • C07D231/50—Acylated on said nitrogen atom

Landscapes

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

Description

  

  Verfahren     zur    Darstellung von     3,5-Dibrom-salicoylamino-antipyrin.       Das vorliegende Patent     betrifft    ein Ver  fahren zur Herstellung von     3,5-Dibrom-sali-          coy        lamino-antipyrin,    welches dadurch ge  kennzeichnet ist, dass man     3,5-Dibrom-,sali-          cy        lsäurechlorid    auf     4-Amino-antipyrin    ein  wirken lässt.  



       Beispiel:     56 g     4-Amino-antipyrin    werden in 10     em3          troclzenem    Chloroform gelöst. Dazu gibt man  durch einen Tropftrichter eine Lösung von  7 0 g     3,:)-Dibrom-salicylsäurechlorid,    gelöst in  250     cm3    Chloroform, innert 15 Minuten zu.  Das Reaktionsgemisch     wird    während 3 Stun  den am     Rückfluss    zum Sieden erhitzt und  nachher abgekühlt. Unter vermindertem  Druck wird das     Lösungsmittel    teilweise ab  destilliert, worauf das,     Säureamid    auskristal  lisiert.

   Nach wiederholtem     Umkristallisieren     aus Essigsäure wird das reine Produkt vom       Stnp.    252      (korr.)    erhalten. Es besitzt die       Formel     
EMI0001.0025     
    Analyse       Bruttozusammensetzung        CisH1r,0sNsBr2.          Ber.        C44,9%    ;     113,1%.     



       Gef.        C44,8%;   <B>H3,2%.</B>



  Process for the preparation of 3,5-dibromo-salicoylamino-antipyrine. The present patent relates to a process for the production of 3,5-dibromo-salicoylamino-antipyrine, which is characterized in that 3,5-dibromo, salicylic acid chloride acts on 4-amino-antipyrine leaves.



       Example: 56 g of 4-amino-antipyrine are dissolved in 10 cubic centimeters of dry chloroform. A solution of 70 g of 3:) - dibromosalicylic acid chloride, dissolved in 250 cm3 of chloroform, is added through a dropping funnel within 15 minutes. The reaction mixture is refluxed for 3 hours and then cooled. The solvent is partially distilled off under reduced pressure, whereupon the acid amide crystallizes out.

   After repeated recrystallization from acetic acid, the pure product of the Stnp. 252 (corr.) Received. It has the formula
EMI0001.0025
    Analysis of gross composition CisH1r, 0sNsBr2. Ber. C44.9%; 113.1%.



       Found C44.8%; <B> H3.2%. </B>

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung von 3,5-Di- brom-salicoylamino-antipyrin, dadurch ge kennzeichnet, dass man 3,5-Dibrom-salicyl- säurechlorid auf 4-Amino-antipyrin einwir- lhen lässt. PATENT CLAIM: Process for the production of 3,5-dibromo-salicoylamino-antipyrine, characterized in that 3,5-dibromo-salicylic acid chloride is allowed to stir onto 4-amino-antipyrine. Die neue Verbindung besitzt die Formel EMI0001.0041 Sie hat den Smp. 252 C (korr.). Analyse: Bruttozusammensetzung CisH1,03i\T3Br2. Ber. C 44,9 % ; 113,1 % . Gef. C 44,8 % ; H 3,2 % . Das. 3, 5 - Dibrom- salicoylamino-antipyrin soll als Fungicid Verwendung finden. The new compound has the formula EMI0001.0041 It has the melting point 252 C (corr.). Analysis: gross composition CisH1.03i \ T3Br2. Ber. C 44.9%; 113.1%. Found C 44.8%; H 3.2%. The. 3, 5 - Dibromosalicoylamino-antipyrine is said to be used as a fungicide.
CH253641D 1945-12-07 1945-12-07 Process for the preparation of 3,5-dibromo-salicoylamino-antipyrine. CH253641A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH246984T 1945-12-07
CH253641T 1945-12-07

Publications (1)

Publication Number Publication Date
CH253641A true CH253641A (en) 1948-03-15

Family

ID=25729150

Family Applications (1)

Application Number Title Priority Date Filing Date
CH253641D CH253641A (en) 1945-12-07 1945-12-07 Process for the preparation of 3,5-dibromo-salicoylamino-antipyrine.

Country Status (1)

Country Link
CH (1) CH253641A (en)

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