CH316971A

CH316971A - Process for the preparation of the semicarbazones of triacetylbenzene

Info

Publication number: CH316971A
Authority: CH
Inventors: Mietzsch Fritz Prof Dr Dr H C; Schmidt Hans Prof Dr Dr H C
Original assignee: Bayer Ag
Priority date: 1952-09-29
Filing date: 1953-09-17
Publication date: 1956-10-31

Description

  

  
 



  Verfahren zur Herstellung der   Senijearbazone    des Triacetylbenzols
Semica.rbazone des s.-Triaeetylbenzols waren bisher unbekannt. Es wurde gefunden, dass man durch Einwirkung von   Semiearbazid      bzw.    dessen Salzen je nach   Mengenverhältnis-    sen und Arbeitsweise in Lösungsmitteln das   Mono.,    Di- oder   Tmsemiearbazon    des genann  tell    Triketons herstellen kann.



   Die Produkte sollen als solche oder als   Zwisehenprodukte    für therapeutische   Zwecke    Verwendung finden, besonders wegen ihrer   cntzündungshemmenden    Wirkung.



   Beispiel 1
20,4 g s.-Triaeetylbenzol werden in 1 Liter Methanol durch Erwärmen gelöst. Dazu gibt man unter Rühren eine Lösung von 35 g Semi  carbazideblorhydrat    und 40 g Natriumacetat in 150   cm3    Wasser. Bald beginnt die Aus  scheidung    des Reaktionsproduktes. Nach einigem Stehen wird abgesaugt und das Produkt durch Behandeln mit warmem Wasser und warmem Methanol gereinigt. Man erhält das Trisemiearbazon des   s.-Triacetylbenzols    in guter Ausbeute als schwach gefärbtes Pulver, das bei   280     noch nicht geschmolzen ist.



   Beispiel 2
20,4 g   s.-Triacetylbenzol    werden in 2 Liter   Methanol    warm gelöst. Zu dieser Lösung lässt man unter Rühren ohne weiteres Erwärmen langsam eine Lösung von 22,5 g Semiearbazidehlorhydrat in 100   cm3    Wasser zulaufen.   Man    rührt noch einige Stunden weiter und lässt bis zur Beendigung der allmählich beginnenden Ausscheidung stehen. Man erhält in guter Ausbeute das Disemiearbazon des   s.-Tria.eetyl-    benzols als schwach gefärbtes Pulver, das gegen 228O unter Zersetzung schmilzt.



   Beispiel 3    20,4    g s.-Triacetylbenzol werden in 1 Liter   Methanol    durch Erwärmen gelöst. Zu dieser Lösung lässt man unter kräftigem Rühren ohne weiteres Erwärmten eine Lösung von 11 g   Semicarbazidehlorhydrat    in 200   ein3    Wasser langsam zutropfen. Allmählich beginnt die   Abseheidung    des Reaktionsproduktes, das man nach beendeter Reaktion durch Absaugen und Auswaschen isoliert. Man erhält das Monosemiearbazon des s.-Triaeetylbenzols in guter Ausbeute als fast farbloses Pulver vom Sehmp. gegen 2330 unter Zersetzung.  



   PATENTANSPRUCH
Verfahren zur Herstellung des Mono-, Dioder   Trisemioarbazons    des   s.-Triaeetylbenzols,    dadurch gekennzeichnet, dass man 1, 2 oder 3 Mol Semiearbazid bzw. dessen Salze in Lösungsmitteln auf   s.-Triacetylbenzol    einwirken lässt. 

**WARNUNG** Ende DESC Feld konnte Anfang CLMS uberlappen**.



   



  
 



  Process for the preparation of the Senijearbazone des Triacetylbenzols
Semica.rbazones of s.-Triaeetylbenzols were previously unknown. It has been found that the action of semi-arbazide or its salts, depending on the proportions and method of operation in solvents, can produce the mono, di- or tri-arbazone of the triketone mentioned.



   The products are intended to be used as such or as intermediate products for therapeutic purposes, particularly because of their anti-inflammatory properties.



   example 1
20.4 g of s-triacetylbenzene are dissolved in 1 liter of methanol by heating. A solution of 35 g of semi-carbazideblorohydrate and 40 g of sodium acetate in 150 cm3 of water is added with stirring. Soon the excretion of the reaction product begins. After standing for a while, it is suctioned off and the product is purified by treating it with warm water and warm methanol. The trisemiearbazone of s.-triacetylbenzene is obtained in good yield as a slightly colored powder which has not yet melted at 280.



   Example 2
20.4 g of s-triacetylbenzene are dissolved in 2 liters of warm methanol. A solution of 22.5 g of semi-arbacid chloride in 100 cm3 of water is slowly added to this solution while stirring without further heating. The mixture is stirred for a few more hours and left to stand until the excretion, which is gradually beginning, has ended. The disemiearbazon of s.-tria.eetylbenzene is obtained in good yield as a pale colored powder which melts towards 228O with decomposition.



   Example 3 20.4 g of s.-triacetylbenzene are dissolved in 1 liter of methanol by heating. A solution of 11 g of semicarbazide chlorohydrate in 200 liters of water is slowly added dropwise to this solution with vigorous stirring without further heating. Gradually, the separation of the reaction product begins, which is isolated by suction and washing after the reaction has ended. The monosemiearbazon of s-triaeetylbenzene is obtained in good yield as an almost colorless powder from Sehmp. around 2330 with decomposition.



   PATENT CLAIM
Process for the preparation of the mono-, di- or trisemioarbazone of s-triacetylbenzene, characterized in that 1, 2 or 3 moles of semi-arbazide or its salts are allowed to act on s-triacetylbenzene in solvents.

** WARNING ** End of DESC field could overlap beginning of CLMS **.

Claims

** WARNING ** Beginning of CLMS field could overlap end of DESC **.

Process for the preparation of the Senijearbazone des Triacetylbenzols Semica.rbazones of s.-Triaeetylbenzols were previously unknown. It has been found that the action of semi-arbazide or its salts, depending on the proportions and method of operation in solvents, can produce the mono, di- or tri-arbazone of the triketone mentioned.

The products are intended to be used as such or as intermediate products for therapeutic purposes, particularly because of their anti-inflammatory properties.

example 1 20.4 g of s-triacetylbenzene are dissolved in 1 liter of methanol by heating. A solution of 35 g of semi-carbazideblorohydrate and 40 g of sodium acetate in 150 cm3 of water is added with stirring. Soon the excretion of the reaction product begins. After standing for a while, it is suctioned off and the product is purified by treating it with warm water and warm methanol. The trisemiearbazone of s.-triacetylbenzene is obtained in good yield as a slightly colored powder which has not yet melted at 280.

Example 2 20.4 g of s-triacetylbenzene are dissolved in 2 liters of warm methanol. A solution of 22.5 g of semi-arbacid chloride in 100 cm3 of water is slowly added to this solution while stirring without further heating. The mixture is stirred for a few more hours and left to stand until the gradual beginning of excretion has ended. The disemiearbazon of s.-tria.eetylbenzene is obtained in good yield as a pale colored powder which melts to 228O with decomposition.

Example 3 20.4 g of s-triacetylbenzene are dissolved in 1 liter of methanol by heating. A solution of 11 g of semicarbazide chlorohydrate in 200 liters of water is slowly added dropwise to this solution with vigorous stirring without further heating. Gradually, the separation of the reaction product begins, which is isolated after the reaction has ended by suction and washing. The monosemiearbazone of s-triaeetylbenzene is obtained in good yield as an almost colorless powder from Sehmp. around 2330 with decomposition.

PATENT CLAIM Process for the preparation of the mono-, di- or trisemioarbazone of s-triacetylbenzene, characterized in that 1, 2 or 3 moles of semi-arbazide or its salts are allowed to act on s-triacetylbenzene in solvents.