DE339101C - Process for the preparation of ethers of p-oxyphenylcarbamide - Google Patents

Process for the preparation of ethers of p-oxyphenylcarbamide

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Publication number
DE339101C
DE339101C DE1920339101D DE339101DD DE339101C DE 339101 C DE339101 C DE 339101C DE 1920339101 D DE1920339101 D DE 1920339101D DE 339101D D DE339101D D DE 339101DD DE 339101 C DE339101 C DE 339101C
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DE
Germany
Prior art keywords
oxyphenylcarbamide
ethers
preparation
water
methyl alcohol
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
DE1920339101D
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German (de)
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.)
Honeywell Riedel de Haen AG
Original Assignee
JD Riedel 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 JD Riedel AG filed Critical JD Riedel AG
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Publication of DE339101C publication Critical patent/DE339101C/en
Expired legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C273/00—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C273/18—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas
    • C07C273/1854—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas by reactions not involving the formation of the N-C(O)-N- moiety

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

Verfahren zur Darstellung von Äthern des p-Oxyphenylcarbamids. Nach dem durch Patent 335877 geschützten Verfahren gelangt man zu Äthern des p-Oxyphenylcarbamids, indem man den Harnstoff des p-Aminophenols mit Halogenalkylen und alkoholischer Alkalilauge behandelt.Process for the preparation of ethers of p-oxyphenylcarbamide. To the process protected by patent 335877 leads to ethers of p-oxyphenylcarbamide, by converting the urea of p-aminophenol with haloalkylene and alcoholic Alkali treated.

Es wurde nun gefunden, daß man bei Ersatz von Halogenalkylen durch mono-halogenierte ein- und mehrwertige Alkohole auf gleiche Weise oxyalkylierteÄther des Oxyphenylcarbamids erhält. Man gelangt z. B. derart auf einfachste Weise in einem einzigen Arbeitsprozeß zu dem Oxäthyl-p-oxyphenylcarbamid, bei dessen Darstellung nach Patent 323298 es der Isolierung zweier umständlich zu gewinnender Zwischenprodukte bedarf.It has now been found that when haloalkylenes are replaced by mono-halogenated monohydric and polyhydric alcohols, oxyalkylated ethers of oxyphenyl carbamide are obtained in the same way. One arrives z. B. so in the simplest way in a single process to the Oxäthyl-p-oxyphenylcarbamide, the preparation of which according to patent 323298 requires the isolation of two cumbersome intermediate products.

Falls der angewandte halogenierte Alkohol durch Alkalialkoholat leicht verseift wird, tut man gut - vgl. Beispiel 2 - den Oxyphenylharnstoff in bereits gelöstem Zustande in Reaktion zu bringen.In case the applied halogenated alcohol easily by alkali alcoholate is saponified, you do well - see Example 2 - the oxyphenylurea in already to bring dissolved states into reaction.

Beispiel r.Example r.

76 g p-Oxyphenylcarbamid werden mit 4.o g Äthylenchlorhydrin und einer Lösung von 11,5 g Natrium in Zoo g Methylalkohol etwa zwei Stunden auf xoo ° erhitzt. Nach dem Erkalten werden zwecks Lösung des angewandten Kochsalzes 400 ccm Wasser zugegeben, der Rückstand abgesogen und aus Wasser umkristallisiert. Man erhält das Oxäthyl-p-oxyphenylcarbamid in Tafeln vom Smp. 16o °. Es entspricht in seinen Eigenschaften dem nach Patent 323298 dargestellten Produkt.76 g of p-oxyphenylcarbamide with 4.o g of ethylene chlorohydrin and one Solution of 11.5 g sodium in zoo g methyl alcohol heated to xoo ° for about two hours. After cooling, 400 ccm of water are used to dissolve the common salt used added, the residue is suctioned off and recrystallized from water. You get that Oxethyl-p-oxyphenylcarbamide in tables with a melting point of 160 °. It corresponds in its properties the product shown according to patent 323298.

Beispiel 2.Example 2.

xo2 g Oxyphenylcarbamid werden in heißem Methylalkohol gelöst und mit einer Lösung von 15 g Natrium in 25o ccm Methylalkohol sowie mit 54 g Glycerin- a -mono -chlorhydrin drei Stunden auf Zoo bis 11o° erhitzt. Nach dem Erkalten wird die Reaktionsmasse mit dem doppelten Volumen Wasser versetzt. Der sich allmählich abscheidende Äther, den man auch durch Abdunsten des Methylalkohols und Anrühren mit Wasser erhalten kann, wird abgesogen und mit einer verdünnten Lösung von Natronlauge gewaschen. Nach dem Umkristallisieren aus Wasser erhält man das Dioxypropyl-p-oxyphenylcarbamid in kugelförmigen Aggregaten vom Smp. r55 bis 156'. Der Äther löst sich in kaltem Wasser sehr schwer, in der Hitze spielend, in allen organischen Solventien ist er schwer löslich.xo2 g of oxyphenylcarbamide are dissolved in hot methyl alcohol and with a solution of 15 g sodium in 25o ccm methyl alcohol and 54 g glycerine a -mono-chlorohydrin heated to 11o ° for three hours at the zoo. After it has cooled down double the volume of water is added to the reaction mass. Which gradually separating ether, which can also be obtained by evaporating the methyl alcohol and stirring it Can be obtained with water, is sucked off and with a dilute solution of sodium hydroxide solution washed. After recrystallization from water, the dioxypropyl-p-oxyphenylcarbamide is obtained in spherical aggregates from m.p. r55 to 156 '. The ether dissolves in cold Very heavy water, playing in the heat, it is in all organic solvents poorly soluble.

Claims (1)

PATENT-ANsPRUCH: Weitere Ausbildung des durch Patent 335877 geschützten Verfahrens zur Darstellung von Äthern des Oxypbenylcarbamids, dadurch gekennzeichnet, daß man den Harnstoff des p-Aminophenols nach den für die Gewinnung von Phenoläthern üblichen Verfahren in die Oxyalkyläther überführt.PATENT CLAIM: Further training of the patented 335877 Process for the preparation of ethers of oxypbenyl carbamide, characterized in that that the urea of p-aminophenol according to the for the production of phenol ethers Conventional processes converted into the oxyalkyl ethers.
DE1920339101D 1920-01-22 1920-01-22 Process for the preparation of ethers of p-oxyphenylcarbamide Expired DE339101C (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE339101T 1920-01-22

Publications (1)

Publication Number Publication Date
DE339101C true DE339101C (en) 1921-07-12

Family

ID=6223288

Family Applications (1)

Application Number Title Priority Date Filing Date
DE1920339101D Expired DE339101C (en) 1920-01-22 1920-01-22 Process for the preparation of ethers of p-oxyphenylcarbamide

Country Status (1)

Country Link
DE (1) DE339101C (en)

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