DE1067819B - Process for the preparation of 2, 5-bis-aethyleneimino-3, 6-bis-acyl-amino-p-benzoquinones - Google Patents
Process for the preparation of 2, 5-bis-aethyleneimino-3, 6-bis-acyl-amino-p-benzoquinonesInfo
- Publication number
- DE1067819B DE1067819B DEC16236A DEC0016236A DE1067819B DE 1067819 B DE1067819 B DE 1067819B DE C16236 A DEC16236 A DE C16236A DE C0016236 A DEC0016236 A DE C0016236A DE 1067819 B DE1067819 B DE 1067819B
- Authority
- DE
- Germany
- Prior art keywords
- bis
- benzoquinones
- preparation
- ethyleneimino
- acyl
- Prior art date
- Legal status (The legal status 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 status listed.)
- Pending
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D203/00—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom
- C07D203/04—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D203/06—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D203/08—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring nitrogen atom
- C07D203/14—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring nitrogen atom with carbocyclic rings directly attached to the ring nitrogen atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Verfahren zur Herstellung von 2,5-Bis-äthylenimino-3,6-bis-acylamino-p-benzochinonen Es ist schon vorgeschlagen worden, 2,5-Bis-äthylenimino-3,6-bis-acylamino-p-benzochinone, wie 2,5-Bisäthylenimino-3,6-bis-acetylamino-p-benzochinone, durch Umsetzung von 2,5-Dihalogen-3,6-bis-acylamino-p-benzochinonen, wie 2,5-Dihalogen-3,6-bis-acetylamino-p-benzochinonen, mit Äthyleniminen herzustellen.Process for the preparation of 2,5-bis-ethyleneimino-3,6-bis-acylamino-p-benzoquinones It has already been proposed to use 2,5-bis-ethylenimino-3,6-bis-acylamino-p-benzoquinones, such as 2,5-Bisäthylenimino-3,6-bis-acetylamino-p-benzoquinone, by reaction of 2,5-dihalo-3,6-bis-acylamino-p-benzoquinones, such as 2,5-dihalo-3,6-bis-acetylamino-p-benzoquinones, to produce with ethylene imines.
Die Erfindung betrifft nun ein Verfahren zur Herstellung von 2,5-Bis-äthylenimino-3,6-bis-acylaminop-benzochinonen der allgemeinen Formel in der R1 und R2 unsubstituierte oder C-alkylierte Äthyleniminogruppen und R3 und R4 Acylreste bedeuten, bei dem man auf 2,5-Bis-äthylenimino-3,6-dihalogenp-benzochinone, in denen die Äthyleniminogruppen ursubstituiert oder C-alkyliert sind, LT-Metallverbindungen, insbesondere Alkalimetallverbindungen, wie Natriumverbindungen, von Carbonsäureamiden, insbesondere aliphatischen Carbonsäureamiden mit 2 bis 6 Kohlenstoffatomen, einwirken läBt. Unter den Dihalogenverbindungen eignen sich besonders die Dichlor- und Dibromverbindungen.The invention now relates to a process for the preparation of 2,5-bis-ethyleneimino-3,6-bis-acylaminop-benzoquinones of the general formula in which R1 and R2 are unsubstituted or C-alkylated ethyleneimino groups and R3 and R4 are acyl radicals in which 2,5-bis-ethyleneimino-3,6-dihalo-p-benzoquinones in which the ethyleneimino groups are unsubstituted or C-alkylated are LT -Metal compounds, especially alkali metal compounds such as sodium compounds, of carboxamides, especially aliphatic carboxamides with 2 to 6 carbon atoms, can act. Among the dihalogen compounds, the dichloro and dibromo compounds are particularly suitable.
Vorzugsweise arbeitet man in indifferenten Lösungsmitteln, wie Dioxan oder Benzol.It is preferred to work in inert solvents such as dioxane or benzene.
Die Ausgangsstoffe sind bekannt oder können in an sich bekannter Weise hergestellt werden.The starting materials are known or can be used in a manner known per se getting produced.
Die neuen Benzochinonverbindungen sind gegen Amoeben, z. B. gegen Entamoeba histolytica, sowie gegen Bakterien wirksam; zudem zeigen sie eine ausgeprägte tumorhemmende Wirkung.The new benzoquinone compounds are against amoebas, e.g. B. against Entamoeba histolytica, as well as effective against bacteria; they also show a pronounced anti-tumor effect.
Die Erfindung wird im nachfolgenden Beispiel näher erläutert.The invention is explained in more detail in the following example.
Beispiel 25,9 g 3,6-Dichlor-2,5-bis-äthylenimino-p-benzochinon werden in 250 cm3 absolutem Dioxan suspendiert. In die gut gerührte Suspension werden bei einer Temperatur zwischen 10 und 25° C 16,2 g Acetamid-Natrium langsam eingetragen. Man rührt 18 Stunden bei Zimmertemperatur, saugt das kristalline Reaktionsprodukt ab und wäscht es gründlich mit Wasser zur Entfernung des gebildeten Natriumchlorids. Zum SchluB wird mit Alkohol gewaschen und getrocknet. Man erhält so das 2,5-Bisäthylenimino-3,6-bis-acetylamino-p-benzochinon der Formel in roten Kristallen vom F. 203° C (Zersetzung).Example 25.9 g of 3,6-dichloro-2,5-bis-ethylenimino-p-benzoquinone are suspended in 250 cm3 of absolute dioxane. 16.2 g of sodium acetamide are slowly added to the well-stirred suspension at a temperature between 10 and 25 ° C. The mixture is stirred for 18 hours at room temperature, the crystalline reaction product is filtered off and washed thoroughly with water to remove the sodium chloride formed. Finally, it is washed with alcohol and dried. This gives 2,5-bisethyleneimino-3,6-bis-acetylamino-p-benzoquinone of the formula in red crystals with a melting point of 203 ° C (decomposition).
In ähnlicher Weise, ausgehend von den entsprechenden Säureamid-Natrium-Salzen, erhält man das 2,5-Bisäthylenimino-3,6-bis-propionylamino-p-benzochinon vom F. 213° C (Zersetzung), das 2,5-Bis-äthylenimino-3,6-bisbutyrylamino-p-benzochinon in roten Kristallen vom F. 214° C (Zersetzung), das 2,5-Bis-(methyl-äthylenimino)-3,6-bis-acetylamino-p-benzochinon in hellroten Kristallen vom F. 199 bis 202° C (Zersetzung) und das 2,5 -Bis- (methyl-äthylenimino) -3,6-bis-propionylaminop-benzochinon in hellroten Kristallen vom F. 209° C.In a similar way, starting from the corresponding acid amide sodium salts, 2,5-Bisäthylenimino-3,6-bis-propionylamino-p-benzoquinone is obtained with a temperature of 213 ° C (decomposition), the 2,5-bis-ethylenimino-3,6-bisbutyrylamino-p-benzoquinone in red Crystals with a melting point of 214 ° C (decomposition), the 2,5-bis (methyl-ethyleneimino) -3,6-bis-acetylamino-p-benzoquinone in light red crystals with a temperature of 199 to 202 ° C (decomposition) and the 2,5-bis- (methyl-ethyleneimino) -3,6-bis-propionylaminop-benzoquinone in light red crystals with a temperature of 209 ° C.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1067819X | 1956-09-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1067819B true DE1067819B (en) | 1959-10-29 |
Family
ID=4555763
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEC16236A Pending DE1067819B (en) | 1956-09-19 | 1956-11-17 | Process for the preparation of 2, 5-bis-aethyleneimino-3, 6-bis-acyl-amino-p-benzoquinones |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1067819B (en) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1010968B (en) | 1955-11-19 | 1957-06-27 | Bayer Ag | Process for the preparation of therapeutically active alkyleneiminoquinones |
-
1956
- 1956-11-17 DE DEC16236A patent/DE1067819B/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1010968B (en) | 1955-11-19 | 1957-06-27 | Bayer Ag | Process for the preparation of therapeutically active alkyleneiminoquinones |
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