DE377816C - Process for the preparation of derivatives of p-substituted phenylureas - Google Patents

Process for the preparation of derivatives of p-substituted phenylureas

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Publication number
DE377816C
DE377816C DEB97913D DEB0097913D DE377816C DE 377816 C DE377816 C DE 377816C DE B97913 D DEB97913 D DE B97913D DE B0097913 D DEB0097913 D DE B0097913D DE 377816 C DE377816 C DE 377816C
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DE
Germany
Prior art keywords
preparation
derivatives
phenylureas
alkyl
substituted
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
DEB97913D
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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.)
Roche Diagnostics GmbH
CF Boehringer und Soehne GmbH
Original Assignee
Boehringer Mannheim GmbH
CF Boehringer und Soehne GmbH
Publication date
Priority to DEB97913D priority Critical patent/DE377816C/en
Application granted granted Critical
Publication of DE377816C publication Critical patent/DE377816C/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 Derivaten p-substituierter Phenylharnstoffe. Das Patent 367611 betrifft ein Verfahren zur Darstellung von p-substituierten as-\-Alkylphenylharnstoffen, das darin besteht, daß man in sekundäre Basen der allgemeinen Formel R'C,H, N H R (worin R Alkyl und R' Alkyl oder Alkoxyl bedeutet) nach bekannten Methoden die Carbamidgruppe einführt. Die nach dieser Arbeitsweise erhältlichen Körper weisen, wie erkannt wurde, gegenüber den bekannten, am Stickstoff nicht alkylierten und als Süßstoffe verwendeten Verbindungen erhebliche Vorzüge hinsichtlich Süßkraft und Löslichkeit auf.Process for the preparation of derivatives of p-substituted phenylureas. The patent 367611 relates to a process for the preparation of p-substituted as - \ - alkylphenylureas, that consists in that in secondary bases of the general formula R'C, H, N H R (where R is alkyl and R 'is alkyl or alkoxyl) according to known methods Introduces carbamide group. The bodies obtainable by this method of operation show as was recognized, compared to the known, not alkylated on nitrogen and Compounds used as sweeteners have considerable sweetening power benefits and solubility.

Es wurde nun gefunden, daß man zu den p-alkoxylierten Stoffen dieser Körperklasse auch gelangen kann, wenn man die as-\-alkylierten p-Oxyphenylharnstoffe nach an sich üblichen Methoden in die Alkyläther überführt. Dieser Weg bietet in Anbetracht der bekannten Zersetzlichkeit und Luftempfindlichkeit der p-Alkoxyphenylamine erhebliche Vorteile.It has now been found that the p-alkoxylated substances of this Body class can also be reached if one uses the as - \ - alkylated p-oxyphenylureas converted into the alkyl ethers by conventional methods. This path offers in In view of the known decomposition and sensitivity to air of p-alkoxyphenylamines significant benefits.

Die Alkylierung kann beispielsweise leicht in der Weise erfolgen, daß man Halogenalkyle auf die in wäßerig-alkoholischer Natronlauge gelösten \ Alkyl-p-oxyphenylharnstoffe bei ioo °, zweckmäßig unter Druck, einwirken läßt.The alkylation can, for example, easily take place in the manner that one haloalkyls dissolved in aqueous-alcoholic sodium hydroxide solution \ alkyl-p-oxyphenylureas at 100 °, expediently under pressure, allowed to act.

Beispiel. . 184 g as-\-3lethy l-p-oxypheny lharnstoff vom F. P. 175' werden in aoo ccm Alkohol unter Zusatt von ioo ccm iofach normaler Natronlauge gelöst, mit iog g Bromäthyl versetzt und im Autoklaven etwa z bis 3 Stunden auf etwa ioo ° erhitzt. Hierauf destilliert man den Alkohol ab und versetzt den Rückstand mit wenig Wasser, wodurch der as-N-ylethyl-p-phenetolharnstoff kristallinisch abgeschieden wird. Danach wird abgesaugt und aus Wasser umkristallisiert.Example. . 184 g as - \ - 3lethy l-p-oxypheny lurea vom F. P. 175 ' are dissolved in aoo ccm alcohol with the addition of 100 ccm 10 times normal sodium hydroxide solution, mixed with iog g of bromoethyl and in the autoclave for about z to 3 hours to about ioo ° heated. The alcohol is then distilled off and the residue is added little water, whereby the as-N-ylethyl-p-phenetolurea deposited in crystalline form will. It is then filtered off with suction and recrystallized from water.

Das Ausgangsmaterial (as-N-llethyl-p-oxyphenylharnstoff) wird erhalten, indem ioo g \-\lethyl-p-amidophenol in 165 ccm 6fach n-Salzsäure gelöst und sodann mit einer Lösung von 73 g Kaliumcyanat in Zoo ccm Wasser versetzt werden. Nach einiger Zeit fällt der as-\-\@fetliyl-p-oxyphenylharnstoff kristallinisch aus. In heißem Alkohol und Wasser ist er leicht löslich, er scheidet sich daraus beim Erkalten in feinen Nädelchen ab. In Äther und Benzol ist er unlöslich. Er schmilzt bei 175'.The starting material (as-N-llethyl-p-oxyphenylurea) is obtained by dissolving 100 g of ethyl-p-amidophenol in 165 cc of 6-fold n-hydrochloric acid and then a solution of 73 g of potassium cyanate in zoo ccm of water is added. After some Time the as - \ - \ @ fetliyl-p-oxyphenylurea precipitates in crystalline form. In hot It is easily soluble in alcohol and water, and separates from it when it cools in fine needles. It is insoluble in ether and benzene. It melts at 175 '.

Claims (1)

PATENT-ANSPRUcFi: Abänderung des durch Patent 367611 geschützten Verfahrens, darin bestehend, daß man zwecks Darstellung von p-alkoxylierten Phenylharnstoffen der allgemeinen Formel R'C,H,NR - CONH., (wo R einen Alkyl-und R' einen Alkoxylrest bedeutet) die p-Oxyphenylharnstoffe der allgemeinen Formel p-OH. C,; H, N R - CON H: in üblicher Weise in die Alkvläther überführt.PATENT CLAIM: Modification of the process protected by patent 367611, consisting in that for the purpose of preparing p-alkoxylated phenylureas of the general formula R'C, H, NR - CONH., (where R is an alkyl and R 'is an alkoxyl radical means) the p-oxyphenylureas of the general formula p-OH. C ,; H, N R - CON H: converted into the alkyl ethers in the usual way.
DEB97913D Process for the preparation of derivatives of p-substituted phenylureas Expired DE377816C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEB97913D DE377816C (en) Process for the preparation of derivatives of p-substituted phenylureas

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEB97913D DE377816C (en) Process for the preparation of derivatives of p-substituted phenylureas

Publications (1)

Publication Number Publication Date
DE377816C true DE377816C (en) 1923-06-28

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Country Status (1)

Country Link
DE (1) DE377816C (en)

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