DE842791C - Process for the preparation of N-aryl-N-vinyl isourea ethers - Google Patents

Process for the preparation of N-aryl-N-vinyl isourea ethers

Info

Publication number
DE842791C
DE842791C DEC2414D DEC0002414D DE842791C DE 842791 C DE842791 C DE 842791C DE C2414 D DEC2414 D DE C2414D DE C0002414 D DEC0002414 D DE C0002414D DE 842791 C DE842791 C DE 842791C
Authority
DE
Germany
Prior art keywords
aryl
vinyl
preparation
ethers
isourea ethers
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.)
Expired
Application number
DEC2414D
Other languages
German (de)
Inventor
Wilhelm Dr Kunze
Carl Theo Dr Schultis
Werner Dr Zerweck
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Cassella Farbwerke Mainkur AG
Original Assignee
Cassella Farbwerke Mainkur AG
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Cassella Farbwerke Mainkur AG filed Critical Cassella Farbwerke Mainkur AG
Priority to DEC2414D priority Critical patent/DE842791C/en
Application granted granted Critical
Publication of DE842791C publication Critical patent/DE842791C/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C273/00Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Description

Verfahren zur Herstellung von N-Aryl-N-vinylisoharnstoffäthern Es wurde gefunden, daß man zu bisher unbekannten N-Aryl-N-vinylisoharnstoffäthern der allgemeinen Formel worin R einen niederen Alkylrest bedeutet, gelangt, wenn man auf N-Aryl-N-ß-halogenäthylcyanami-de Ätzalkalien in Gegenwart eines niederen Alkohols einwirken läBt. DaB man auf diese Weise die genannten Isa'harnstoffäther in glatter Reaktion und guter Ausbeute erhält, ist schon aus dem Grund überraschend, weil man bei vorliegendem Verfahren in alkalischem Medium arbeitet, während alle bisher bekannten Darstellungsweisen für Isoharnstoffäther aus den entsprechenden Cyanverbindungen auf das Arbeiten in saurem Medium abgestellt sind.Process for the preparation of N-aryl-N-vinyl isourea ethers It has been found that one can obtain previously unknown N-aryl-N-vinyl isourea ethers of the general formula in which R denotes a lower alkyl radical is obtained if N-aryl-N-ß-halogenethylcyanamides are allowed to act in the presence of a lower alcohol. The fact that the said isa'urea ethers are obtained in this way in a smooth reaction and good yield is surprising for the reason that the present process is carried out in an alkaline medium, while all previously known methods of preparation of isourea ethers from the corresponding cyano compounds are based on the work in acidic medium are turned off.

Die vorliegenden neuen Verbindungen sollen als Zwischenprodukte, insbesondere zur Herstellung von Polymerisaten, Verwendung finden.The present new compounds are intended as intermediates, in particular for the production of polymers, use.

Beispiel 225 Teile N-f-Bromäthyl-N-phenylcyanamid (Ber. dtsch. chem. Ges. 33, 1384) werden in etwa 4oo Teilen Äthylallkohol gelöst. In diese Lösung läBt man bei 5 bis io° eine Lösung von 7o Teilen Kaliumhydroxyd in etwa 4oo Teilen Äthylalkohol einlaufen. Man rührt etwa 20 Stunden, wobei die "Temperatur nach den ersten 6 Stunden auf 20 bis 25' ansteigen kann, und filtriert dann vorn ausgefallenen Kaliurnbromid ab. Aus dem Filtrat xvirci der Alkohol abdestilliert und der Rückstand' in N\'asser aufgenommen, wobei sieh das Reaktionsprodukt als 01 abscheidet. Mit Hilfe von Methylenchlorid wird das öl vom Wasser getrennt. Nach Abdestillieren des :@l,ethylenchlorids wird im Vakuum fraktioniert, wobei der N-Phenyl-N-vinylisoharnstofl'äthyläther bei Kp15 130 bis r31° übergeht. Der in entsprechender Weise hergestellte i'4- Tolyl-N-viny'lisoharnstoffärhyläther siedet bei Kp3 I 18 bi S I20'. Bei Verwendiumg von '\letfliylalkohol an Stelle von Äthylalkohol erhält man die entsprechendien .\lethylätaher. Example 225 parts of Nf-bromoethyl-N-phenylcyanamide (Ber. Dtsch. Chem. Ges. 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 allowed to run into this solution at 5 to 10 °. The mixture is stirred for about 20 hours, during which the temperature can rise to 20 to 25 minutes 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, with The reaction product separates out as 01. The oil is separated from the water with the aid of methylene chloride, and after the methylene chloride has been distilled off, it is fractionated in vacuo, the N-phenyl-N-vinylisourea ethyl ether passing over at a boiling point of 130 to r31 °. The correspondingly produced i'4- Tolyl-N-viny'lisourstoffärhyläther boils at boiling point 3 I 18 to S I20 '. If '\ letfliyl alcohol is used instead from ethyl alcohol one obtains the corresponding values . \ lethylether.

Claims (1)

PATEXTANS PR t.i.H:
Verfahren zur Herstellung von N-Aryl-N-vinylisoharnstoffäthern, dadurch gekennzeichnet, daB man N - Aryl - N - ß - 9ialogenäthylcyanamide mit Ätzalkalien in Gegenwart eipes niederen Alkohols behandelt.
PATEXTANS PR tiH:
Process for the preparation of N-aryl-N-vinyl isourea ethers, characterized in that N - aryl - N - ß - 9ialogenethylcyanamides are treated with caustic alkalis in the presence of a lower alcohol.
DEC2414D 1944-09-12 1944-09-12 Process for the preparation of N-aryl-N-vinyl isourea ethers Expired DE842791C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEC2414D DE842791C (en) 1944-09-12 1944-09-12 Process for the preparation of N-aryl-N-vinyl isourea ethers

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEC2414D DE842791C (en) 1944-09-12 1944-09-12 Process for the preparation of N-aryl-N-vinyl isourea ethers

Publications (1)

Publication Number Publication Date
DE842791C true DE842791C (en) 1952-06-30

Family

ID=7012913

Family Applications (1)

Application Number Title Priority Date Filing Date
DEC2414D Expired DE842791C (en) 1944-09-12 1944-09-12 Process for the preparation of N-aryl-N-vinyl isourea ethers

Country Status (1)

Country Link
DE (1) DE842791C (en)

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