CH188983A - Process for the preparation of di- (3,4-diaminochinaldyl-6) urea. - Google Patents
Process for the preparation of di- (3,4-diaminochinaldyl-6) urea.Info
- Publication number
- CH188983A CH188983A CH188983DA CH188983A CH 188983 A CH188983 A CH 188983A CH 188983D A CH188983D A CH 188983DA CH 188983 A CH188983 A CH 188983A
- Authority
- CH
- Switzerland
- Prior art keywords
- preparation
- urea
- diaminochinaldyl
- hydrochloric acid
- nitro
- Prior art date
Links
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung von Di-(3. 4-Diaminoehinaldyl-6)-harnstoff. Im Patent Nr. 1785.39 ist die Darstellung des 3-Nitro-4.6-diaminochinaldins beschrie ben, das als Zwischenprodukt für Arznei mittel wichtig ist.
Gegenstand der vorliegender Erfindung ist ein Verfahren zur Darstellung von Di- (3.4-diaminochinaldyl-6)-harnstoff, das da durch gekennzeichnet ist, dass man 3-Nitro- 4.6-diaminochinaldin mit Phosgen umsetzt und die Nitrogruppe des so erhaltenen Pro duktes reduziert.
Die neue Verbindung ist in organischen Lösungsmitteln fast unlöslich, sie bildet ein in Wasser beim Erwärmen leicht lösliches, sich bei<B>2,68'</B> zersetzendes salzsaures Salz. Sie soll als Heilmittel Verwendung finden. <I>Beispiel:</I> In eine -#vässirige Aufschlämmung von 22 g 3 - Nitro - 4 . 6 - diaminochinaldin in etwa 200 cm' Wasser wird unter Rühren, und Er wärmen im Wasserbad Phosgen eingeleitet.
Nachdem saure Reaktion eingetreten ist, wird mit Natronlauge alkalisch gemacht unter weiterem Einleiten von Phosgen. Dies: wird so oft wiederholt, bis in einer Probe keine freie 6-Aminogruppe mehr nachweisbar ist. Darauf wird die salzsaure Reaktionsmasse heiss abgesaugt und mit verdünnter Salzsäure gewaschen.
Sie stellt das salzsaure Salz des Di-Nitroaminochinaldylharnstoffes dar, das in der 2:Ofachen Menge 50%iger Essigsäure unter Rühren und Erwärmen im Wasserbad mit Eisenpulver reduziert wird. Die heisse Lösung wird filtriert, .das Filtrat mit Salz säure kongosauer gemacht und mit Chlor natriumlösung versetzt.
Dabei scheidet sich das fast farblose salzsaure Salz der Verbin dung folgender Formel aus:
EMI0001.0045
das abgesaugt und mit verdünnter Salzsäure gewaschen wird. Es entsteht in einer Menge von 21 g, ist beim Erwärmen in Wasser leicht löslich und zersetzt sich bei 268 un ter Schwarzfärbung. Die Base wird aus der Lösung durch Alkali als dicke Gallerte ge fällt und ist in organischen Lösungsmitteln fast unlöslich.
Process for the preparation of di- (3,4-diaminoaldehaldyl-6) urea. In patent no. 1785.39, the preparation of 3-nitro-4,6-diaminochinaldine is described ben, which is important as an intermediate for drugs.
The present invention relates to a process for the preparation of di- (3,4-diaminochinaldyl-6) urea which is characterized in that 3-nitro-4,6-diaminochinaldine is reacted with phosgene and the nitro group of the product thus obtained is reduced.
The new compound is almost insoluble in organic solvents; it forms a hydrochloric acid salt that is easily soluble in water when heated and decomposes at <B> 2.68 '</B>. It is said to be used as a remedy. <I> Example: </I> In a - # watery slurry of 22 g 3 - Nitro - 4. 6 - diaminochinaldin in about 200 cm 'of water is introduced with stirring, and he warm phosgene in a water bath.
After an acidic reaction has occurred, it is made alkaline with sodium hydroxide solution while further introducing phosgene. This is repeated until no more free 6-amino groups can be detected in a sample. The hydrochloric acid reaction mass is then filtered off with suction while hot and washed with dilute hydrochloric acid.
It represents the hydrochloric acid salt of di-nitroaminoquinochinaldylurea, which is reduced in 2: O times the amount of 50% acetic acid while stirring and heating in a water bath with iron powder. The hot solution is filtered, the filtrate is made Congo acidic with hydrochloric acid and a sodium chloride solution is added.
The almost colorless hydrochloric acid salt of the compound of the following formula is separated out:
EMI0001.0045
which is filtered off and washed with dilute hydrochloric acid. It is produced in an amount of 21 g, is easily soluble in water when heated and decomposes when it turns black at 268. The base is precipitated from the solution by alkali as a thick jelly and is almost insoluble in organic solvents.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE188983X | 1933-09-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH188983A true CH188983A (en) | 1937-01-31 |
Family
ID=5721123
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH188983D CH188983A (en) | 1933-09-28 | 1934-09-24 | Process for the preparation of di- (3,4-diaminochinaldyl-6) urea. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH188983A (en) |
-
1934
- 1934-09-24 CH CH188983D patent/CH188983A/en unknown
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