CH314849A - Process for the preparation of N-guanyl-N'-p-guanylphenyl-diacetyl-dihydrazone dihydrochloride - Google Patents
Process for the preparation of N-guanyl-N'-p-guanylphenyl-diacetyl-dihydrazone dihydrochlorideInfo
- Publication number
- CH314849A CH314849A CH314849DA CH314849A CH 314849 A CH314849 A CH 314849A CH 314849D A CH314849D A CH 314849DA CH 314849 A CH314849 A CH 314849A
- Authority
- CH
- Switzerland
- Prior art keywords
- dihydrochloride
- diacetyl
- guanyl
- guanylphenyl
- dihydrazone
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 4
- 239000000843 powder Substances 0.000 claims description 3
- INLSFDXMHGITFI-UHFFFAOYSA-N 2-hydrazinylbenzenecarboximidamide Chemical compound N(N)C1=C(C(=N)N)C=CC=C1 INLSFDXMHGITFI-UHFFFAOYSA-N 0.000 claims description 2
- 208000010362 Protozoan Infections Diseases 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 239000007859 condensation product Substances 0.000 claims description 2
- 239000000243 solution Substances 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 238000000354 decomposition reaction Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- WPANETAWYGDRLL-UHFFFAOYSA-N 4-aminobenzenecarboximidamide Chemical compound NC(=N)C1=CC=C(N)C=C1 WPANETAWYGDRLL-UHFFFAOYSA-N 0.000 description 1
- NWGUVJQVFQVAHS-UHFFFAOYSA-N 4-hydrazinylbenzenecarboximidamide Chemical compound NNC1=CC=C(C(N)=N)C=C1 NWGUVJQVFQVAHS-UHFFFAOYSA-N 0.000 description 1
- QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical group CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 description 1
- 239000012675 alcoholic extract Substances 0.000 description 1
- HAMNKKUPIHEESI-UHFFFAOYSA-N aminoguanidine Chemical compound NNC(N)=N HAMNKKUPIHEESI-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- UWPPADMWQVNQFC-UHFFFAOYSA-J tetrachlorostannane;hydrochloride Chemical compound Cl.Cl[Sn](Cl)(Cl)Cl UWPPADMWQVNQFC-UHFFFAOYSA-J 0.000 description 1
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)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung von N-Guanyl-N'-p-guanylphenyl-diacetyl-dihydrazon-dihydrochlorid
Gegenstand der vorliegenden Erfindung ist ein Verfahren zur Herstellung von N Guanyl-N'-, p-guanylphenyl-diacetyl-dihydra zon-dihydroehlorid der Formel
EMI1.1
das dadurch gekennzeichnet ist, dass man p Hydrazino-benzamidin mit Diacetyl-mono- gxlanvlhydrazon kondensiert und das Kondensationsprodukt als Dihydrochlorid isoliert.
Die neue Verbindung ist ein bhssgelbes Pulver und zeiehnet sich durch Wirksamkeit gegen protozoisehe Infektionen aus.
Beispiel
Durch Reduktion einer salzsauren Diazoniumlösung von p-Aminobenzamidin mit einer stark salzsauren Zinnchlorürlösung bei-10 bis-5 , Entzinnung der Losung und Verdampfen zur Trockne im Vakuum nach Neutralisation mit Natronlauge, Ausziehen des Rüekstandes mit Alkohol und Versetzen des alkoholisehen Auszuges mit Äther erhält man das Dihydroehlorid des als Ausgangsstoff verwendeten p-Hydrazino-benzamidins, das nach dem Umkristallisieren aus Alkohol bei 211 bis 212 unter Zersetzung schmilzt.
Eine Losung von 3 g dieses Salzes wird mit einer heissen wässerigen Lösung von 1, 75 g Diacetyl-monoguanylhydrazon vermischt und die Mischung mit verdünnter Salzsäure angesäuert. Nach einiger Zeit wird übersehüssige verdünnte Salzsäure zugesetzt, nach Kühlen in Eis das Dihydrochlorid obiger Formel abgesaugt und mit eiskalter verdünnter Salzsäure und Aceton gewaschen. Das blassgelbe Pulver löst sich mit gelber Farbe in Wasser.
Aus einer Lösung des Dihydrochlolids kann mit verdünnter Natronlauge die fast farblose Base, das Diacetyl- (N-guanyl)- (N-p guanyl-phenyl)-dihydrazon, F. = 240241 (Zersetzung), erhalten werden.
Das als Ausgangsstoff verwendete Diace tyl-mono-guanylhydrazon (aus Wasser umkri ; tall. isiert, F. = 214 unter heftiger Zerset zung) kann durch vorsichtige Umsetzung von Diacetyl mit salzsaurem Aminoguanidin erhalten werden.
Process for the preparation of N-guanyl-N'-p-guanylphenyl-diacetyl-dihydrazone dihydrochloride
The present invention relates to a process for the preparation of N guanyl-N'-, p-guanylphenyl-diacetyl-dihydra zon dihydrochloride of the formula
EMI1.1
which is characterized in that p hydrazino-benzamidine is condensed with diacetyl-monogxlanvlhydrazone and the condensation product is isolated as dihydrochloride.
The new compound is a pale yellow powder and is effective against protozoan infections.
example
This is obtained by reducing a hydrochloric acid diazonium solution of p-aminobenzamidine with a strongly hydrochloric acid tin chloride solution at -10 to -5, detinning the solution and evaporating to dryness in vacuo after neutralization with sodium hydroxide solution, extracting the residue with alcohol and adding ether to the alcoholic extract Dihydrochloride of the p-hydrazino-benzamidine used as the starting material, which, after recrystallization from alcohol, melts at 211 to 212 with decomposition.
A solution of 3 g of this salt is mixed with a hot aqueous solution of 1.75 g of diacetyl-monoguanylhydrazone and the mixture is acidified with dilute hydrochloric acid. After some time, excess dilute hydrochloric acid is added, and after cooling in ice, the dihydrochloride of the above formula is filtered off with suction and washed with ice-cold dilute hydrochloric acid and acetone. The pale yellow powder dissolves in water with a yellow color.
The almost colorless base, diacetyl- (N-guanyl) - (N-p guanyl-phenyl) -dihydrazone, m.p. = 240241 (decomposition), can be obtained from a solution of the dihydrochlolide with dilute sodium hydroxide solution.
The diacetyl-mono-guanylhydrazone used as the starting material (recrystallized from water, metalized, F. = 214 with violent decomposition) can be obtained by careful reaction of diacetyl with hydrochloric aminoguanidine.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE314848X | 1950-07-24 | ||
| DE314849X | 1950-07-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH314849A true CH314849A (en) | 1956-06-30 |
Family
ID=32991744
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH314849D CH314849A (en) | 1950-07-24 | 1951-07-16 | Process for the preparation of N-guanyl-N'-p-guanylphenyl-diacetyl-dihydrazone dihydrochloride |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH314849A (en) |
-
1951
- 1951-07-16 CH CH314849D patent/CH314849A/en unknown
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