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 dihydrochlorideInfo
- 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
Links
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
Landscapes
- 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)
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) |
-
1951
- 1951-07-16 CH CH314848D patent/CH314848A/en unknown
- 1951-07-16 CH CH307133D patent/CH307133A/en unknown
Also Published As
Publication number | Publication date |
---|---|
CH307133A (en) | 1955-05-15 |
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