CH295667A - Process for the preparation of an N-aryl-N-vinyl-isoureaether. - Google Patents
Process for the preparation of an N-aryl-N-vinyl-isoureaether.Info
- Publication number
- CH295667A CH295667A CH295667DA CH295667A CH 295667 A CH295667 A CH 295667A CH 295667D A CH295667D A CH 295667DA CH 295667 A CH295667 A CH 295667A
- Authority
- CH
- Switzerland
- Prior art keywords
- aryl
- vinyl
- isoureaether
- preparation
- phenyl
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/70—Compounds containing any of the groups, e.g. isoureas
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines N-Aryl-N-vinyl-isoharnstoffäthers. Es wurde gefunden, dass man zu bisher unbekannten h,T-Aryl-N-vinz-1-isoharnstoff- äthern der allgemeinen Formel
EMI0001.0007
worin II einen niederen Alkylrest bedeutet, gelangt, wenn man auf N-Aryl-N-ss-IIalogen- ätliyl-cyanamide Ätzalkalien in Gegenwart eines niederen Alkohols einwirken lässt.
Dass man auf diese Weise die genannten Isoharnstoffäther in glatter Reaktion und guter Ausbeute erhält, ist schon aus dem (Irunde überraschend, weil man bei vorlie gendem Verfahren in alkalischem Medium ar beitet, während alle bisher bekannten Dar- stel.l.ungSweisen für Isoharnstoffäther aus den entsprechenden Cyanverbindungen auf. das Arbeiten in saurem Medium abgestellt sind.
Diese neuen Verbindungen sollen als Zwi- ehenprodukte, insbesondere zur Herstellung ,von Polymerisaten, Verwendung finden.
Gegenstand des vorliegenden Patentes ist nun ein Verfahren zur Herstellung eines N - Ary 1-N-vinyl - isoharnstoffäthers, welches dadurch gekennzeichnet ist, dass man N- Phenyl-N-fl-bromäthyl-cyanamid mit Ätzkali in Gegenwart von Äthylalkohol behandelt. <I>Beispiel:</I> 225 Teile f-Bromäthyl-phenyl-cyanamid (Ber. 33, 1384) werden in etwa 400 Teilen Äthylalkohol gelöst. In diese Lösung lässt man bei 5-10 eine Lösung von 70 Teilen Kalium hydroxyd in etwa 400 Teilen Äthylalkohol. einlaufen.
Man rührt etwa 20 Stunden, wo bei die Temperatur nach den ersten 6 Stun den auf 20-25 ansteigen kann, und filtriert dann vom ausgefallenen Kaliumbromid ab. Aus dem Filtrat wird der Alkohol abdestil- liert und der Rückstand in Wasser aufgenom men, wobei sich das Reaktionsprodukt als Öl abscheidet. Mit Hilfe von Methylenchlorid wird das Öl vom Wasser getrennt. Nach<B>Ab-</B> destillieren des lbIethylenchlorids wird im Vakuum fraktioniert, wobei der erhaltene N-Phenyl-N-vinyl-isoharnstoffäthyläther bei Kp15 130-131 übergeht.
Process for the preparation of an N-aryl-N-vinyl-isoureaether. It has been found that h, T-aryl-N-vinz-1-isourea ethers of the general formula can be obtained so far unknown
EMI0001.0007
where II denotes a lower alkyl radical, is obtained when N-aryl-N-ss-IIalogen-ätliyl-cyanamide caustic alkalis are allowed to act in the presence of a lower alcohol.
The fact that the mentioned isourea ethers are obtained in this way in a smooth reaction and good yield is already surprising from the (Irunde, because in the present process one works in an alkaline medium, while all previously known methods of preparation for isourea ethers the corresponding cyano compounds, working in an acidic medium are turned off.
These new compounds are intended to be used as intermediate products, in particular for the production of polymers.
The subject of the present patent is a process for the production of an N - ary 1-N-vinyl - isourea ether, which is characterized in that N-phenyl-N-fl-bromoethyl-cyanamide is treated with caustic potash in the presence of ethyl alcohol. <I> Example: </I> 225 parts of f-bromoethyl-phenyl-cyanamide (Ber. 33, 1384) are dissolved in about 400 parts of ethyl alcohol. A solution of 70 parts of potassium hydroxide in about 400 parts of ethyl alcohol is left in this solution at 5-10. come in.
The mixture is stirred for about 20 hours, where the temperature can rise to 20-25 after the first 6 hours, and the precipitated potassium bromide is then filtered off. The alcohol is distilled off from the filtrate and the residue is taken up in water, the reaction product separating out as an oil. The oil is separated from the water with the help of methylene chloride. After the IbIethylene chloride has been distilled off, the fractionation is carried out in vacuo, the N-phenyl-N-vinyl-isoureaethyl ether obtained passing over at boiling point 130-131.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE295667X | 1944-09-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH295667A true CH295667A (en) | 1954-01-15 |
Family
ID=6090123
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH295667D CH295667A (en) | 1944-09-11 | 1951-07-28 | Process for the preparation of an N-aryl-N-vinyl-isoureaether. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH295667A (en) |
-
1951
- 1951-07-28 CH CH295667D patent/CH295667A/en unknown
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