CH314848A - Process for the preparation of guanylhydrazo-pyruvaldehyde-p- (guanyl-hydrazo-formyl) -phenylhydrazone dihydrochloride - Google Patents

Process for the preparation of guanylhydrazo-pyruvaldehyde-p- (guanyl-hydrazo-formyl) -phenylhydrazone dihydrochloride

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Publication number
CH314848A
CH314848A CH314848DA CH314848A CH 314848 A CH314848 A CH 314848A CH 314848D A CH314848D A CH 314848DA CH 314848 A CH314848 A CH 314848A
Authority
CH
Switzerland
Prior art keywords
guanyl
phenylhydrazone
dihydrochloride
formyl
pyruvaldehyde
Prior art date
Application number
Other languages
German (de)
Inventor
Heinrich Dr Jensch
Original Assignee
Hoechst 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 Hoechst Ag filed Critical Hoechst Ag
Publication of CH314848A publication Critical patent/CH314848A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C281/00—Derivatives of carbonic acid containing functional groups covered by groups C07C269/00 - C07C279/00 in which at least one nitrogen atom of these functional groups is further bound to another nitrogen atom not being part of a nitro or nitroso group
    • C07C281/16—Compounds containing any of the groups, e.g. aminoguanidine
    • C07C281/18—Compounds containing any of the groups, e.g. aminoguanidine the other nitrogen atom being further doubly-bound to a carbon atom, e.g. guanylhydrazones

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

Description

  

  



  Verfahren zur Herstellung von   Guanylhydrazono-brenztraubenaldehyd-p. (guanyl-hydrazono-       formyl)-phenylhydrazon-dihydrochlorid   
Gegenstand der vorliegenden Erfindung ist ein Verfahren zur Herstellung von   Guanyl-      hydrazono-brenztraubenaldehyd-p-    (guanyl  hydrazono-formyl)-phenylhydrazon-dihydro-    chlorid der Formel
EMI1.1     
 das dadurch gekennzeichnet ist, dass man Brenztraubenaldehyd-p- (guanyl-hydrazono  formyl)-phenylhydrazon    mit Aminoguanidin kondensiert und das Kondensationsprodukt als Dihydrochlorid isoliert.



   Die neue Verbindung ist ein rotbraunes Pulver und zeichnet sich durch Wirksamkeit gegen protozoische Infektionen aus.



   Beisptel
14 g Brenztraubenaldehyd-p-(guanyl-hy    drazono-formyl)-phenylhydrazon-hydrochlorid    werden mit   70      em3 Wasser lmd    einer Lösung von 7,5 g Aminoguanidin-Carbonat in etwa 35   em3    2N-Salzsäure bis zur   volligen    Lösung im Wasserbad erwärmt, worauf mit   über-    schüssiger Salzsäure versetzt und das Dihydrochlorid obiger Formel nach guter Kühlung   abgesa. ugt und    mit eiskalter   verdiinnter    Salzsäure und Aceton gewaschen wird. Es bildet ein rotbraunes Pulver, das in Wasser mit roter   Farbe leieht löslich    ist. Nach dem Umkristallisieren aus Methanol und Aceton : braunes, kristallines Pulver, F. = 266  (Zersetzung).



   Das als Ausgangsmaterial verwendete   Hy-    drazon kann aus p-Amino-benzalguanylhydrazon und Acetessigsäure hergestellt werden ; aus Wasser umkristallisiert bildet es ein braunrotes Pulver vom F. = 120  (Zersetzung).



  Das p-Amino-benzalguanylhydrazon seinerseits kann als Carbonat durch Fällen des mit verdünnter Salzsäure verseiften p-Acetamino   benzalguanylhydrazons[ausWasserumkristal-    lisiert, F. =   238     (Zersetzung)] mit Pottasehe als gelbes Pulver erhalten werden, F. = 235  (Zersetzung).



  



  Process for the preparation of guanylhydrazono-pyruvaldehyde-p. (guanyl-hydrazonoformyl) -phenylhydrazone dihydrochloride
The present invention relates to a process for the preparation of guanyl hydrazono-pyruvic aldehyde-p- (guanyl hydrazono-formyl) -phenylhydrazone dihydrochloride of the formula
EMI1.1
 which is characterized in that pyruvic aldehyde-p- (guanyl-hydrazono formyl) -phenylhydrazone is condensed with aminoguanidine and the condensation product is isolated as dihydrochloride.



   The new compound is a red-brown powder and is characterized by its effectiveness against protozoan infections.



   Example
14 g of pyruvic aldehyde-p- (guanyl-hy drazono-formyl) -phenylhydrazone hydrochloride are heated with 70 em3 water in a solution of 7.5 g aminoguanidine carbonate in about 35 em3 2N hydrochloric acid until completely dissolved in a water bath, whereupon excess hydrochloric acid is added and the dihydrochloride of the above formula is filtered off after good cooling. and washed with ice-cold diluted hydrochloric acid and acetone. It forms a red-brown powder that is slightly soluble in water with a red color. After recrystallization from methanol and acetone: brown, crystalline powder, mp = 266 (decomposition).



   The hydrazone used as the starting material can be prepared from p-amino-benzalguanylhydrazone and acetoacetic acid; Recrystallized from water, it forms a brown-red powder of F. = 120 (decomposition).



  The p-amino-benzalguanyl hydrazone, for its part, can be obtained as a carbonate by precipitating the p-acetaminobenzalguanyl hydrazone, saponified with dilute hydrochloric acid [from water crystallized, F. = 238 (decomposition)] with Pottasehe as a yellow powder, F. = 235 (decomposition).

Claims (1)

PATENTANSPRUCH Verfahren zur Herstelhmg von Guanyl- hydrazono-brenztraubenaldehyd-p- (guanyl- hydrazono-formyl)-phenylhydrazon-dihydro ehlorid, dadurch gekennzeichnet, dass man Brenztraubenaldehyd-p- (guanyl-hydrazono- formyl)-phenylhydrazon mit Aminoguanidin kondensiert und das Eondensationsprodukt als Dihydrochlorid isoliert. PATENT CLAIM Process for the production of guanyl hydrazono-pyruvaldehyde-p- (guanyl-hydrazono-formyl) -phenylhydrazone-dihydrochloride, characterized in that pyruvic aldehyde-p- (guanyl-hydrazonoformyl) -phenylhydrazone is condensed with aminoguanidine and the condensation product Dihydrochloride isolated. Die neue Verbindung ist ein rotbraunes Pulver und zeichnet sieh durch'Wirksamkeit gegen protozoische Infektionen aus. The new compound is a red-brown powder and is characterized by its effectiveness against protozoan infections.
CH314848D 1950-07-24 1951-07-16 Process for the preparation of guanylhydrazo-pyruvaldehyde-p- (guanyl-hydrazo-formyl) -phenylhydrazone dihydrochloride CH314848A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE307133X 1950-07-24
DE314848X 1950-07-24

Publications (1)

Publication Number Publication Date
CH314848A true CH314848A (en) 1956-06-30

Family

ID=32991740

Family Applications (2)

Application Number Title Priority Date Filing Date
CH314848D CH314848A (en) 1950-07-24 1951-07-16 Process for the preparation of guanylhydrazo-pyruvaldehyde-p- (guanyl-hydrazo-formyl) -phenylhydrazone dihydrochloride
CH307133D CH307133A (en) 1950-07-24 1951-07-16 Process for the preparation of guanylhydrazono-pyruvaldehyde-p-guanyl-phenylhydrazone-carbonate.

Family Applications After (1)

Application Number Title Priority Date Filing Date
CH307133D CH307133A (en) 1950-07-24 1951-07-16 Process for the preparation of guanylhydrazono-pyruvaldehyde-p-guanyl-phenylhydrazone-carbonate.

Country Status (1)

Country Link
CH (2) CH314848A (en)

Also Published As

Publication number Publication date
CH307133A (en) 1955-05-15

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