DE332204C - Process for the preparation of acyl derivatives of a p-aminophenol ether - Google Patents

Process for the preparation of acyl derivatives of a p-aminophenol ether

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Publication number
DE332204C
DE332204C DE1917332204D DE332204DD DE332204C DE 332204 C DE332204 C DE 332204C DE 1917332204 D DE1917332204 D DE 1917332204D DE 332204D D DE332204D D DE 332204DD DE 332204 C DE332204 C DE 332204C
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DE
Germany
Prior art keywords
parts
acyl derivatives
preparation
alcohol
water
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
DE1917332204D
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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.)
Chemische Ind Ges
GESELLSCHAFT fur CHEMISCHE INDUSTRIE
BASF Schweiz AG
Original Assignee
Chemische Ind Ges
GESELLSCHAFT fur CHEMISCHE INDUSTRIE
Gesellschaft fuer Chemische Industrie in Basel CIBA
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Application filed by Chemische Ind Ges, GESELLSCHAFT fur CHEMISCHE INDUSTRIE, Gesellschaft fuer Chemische Industrie in Basel CIBA filed Critical Chemische Ind Ges
Application granted granted Critical
Publication of DE332204C publication Critical patent/DE332204C/en
Expired legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms

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

Description

Verfahren zur Darstellung von Acylderivaten eines p-Aiiiinophenoläthers. Das Patent 31o967 betrifft ein Verfahren zur Darstellung von Acylderivaten des p-AminophenolallyJäther>, welches darin besteht, daß man p-Aminophenolall#läther mit aliphatischen Säuren, Säureanhydriden oder Säurehalogeniden, gegebenenfalls in Gegenwart geeigneter Verdünnungs- oder Kondensationsmittel, zur Reaktion bringt. Es wurde nun gefunden, daß man auch dadurch zu diesen therapeutisch wertvollen Acylderivaten des p-Aminol)henolallylätbers gelangen kann, wenn man die Acylderivate des p-Aminoplienols mit einem Allylhalegenid und Alkali behandelt.Process for the preparation of acyl derivatives of a p-amino phenol ether. The patent 31o967 relates to a process for the preparation of acyl derivatives of p-aminophenolally ether>, which consists in p-aminophenolall # ethers with aliphatic acids, Acid anhydrides or acid halides, optionally in the presence of suitable diluents or condensing agent. It has now been found that one too this leads to these therapeutically valuable acyl derivatives of p-aminol) henolallyl ether can be achieved if the acyl derivatives of p-aminoplienol with an allyl halide and alkali treated.

Das Verfahren wird durch folgende Beispiele erläutert.-Beispiel i.The method is illustrated by the following examples. Example i.

1:42 Teile Acet-p-aminoi)lienol werden in 2ooTeilen Alkohol gelöst. Zu der Lösung fügt man eine Lösung von 4oTeilen Ätznatron in iooTeileii Wasser und i2iTeile Allylbromid hinzu. Man erwärmt unter Rühren im Wasserbad zwei Stunden bei 6o bis 8o' und verdünnt die Reaktionsmasse mit Wasser, worauf der p-Acetaminophenolallyläther als rasch erstarrendes 01 ausfällt. Man kristallisiert denselben aus Wasser um und erhält glänzende Blättchen vom Schmelzpunkt 94'. Beispiel 2.1:42 parts of acet-p-aminoi) lienol are dissolved in 2oo parts of alcohol. A solution of 40 parts of caustic soda in 100 parts of water and 12 parts of allyl bromide is added to the solution. The mixture is heated with stirring in a water bath for two hours at 6o-8o 'and diluting the reaction mass with water, whereupon the p-Acetaminophenolallyläther as rapidly solidifying 01 fails. It is recrystallized from water and shiny flakes with a melting point of 94 'are obtained. Example 2.

179Teile Laktyl-p-aminophenol werden in 3oo Teilen Alkohol gelöst und mit 121 Teilen Allylbromid versetzt. Man fügt hierauf eine Lösung von 56 Teilen Ätzkali in 2oo Teilen Alkohol hinzu und kocht während 48 Stunden am Rückflußkühler. Man filtriert hierauf vom ausgeschiedenen Bromkali ab, destilliert den größten Teil des " Alkohols ab und versetzt den Rückstand mit Wasser. Der entstandene Laktyl-p--#iminophenolallylätlier erstarrt kristallinisch und wiid aus Wasser umkristallisiert. Er besitzt die in dem Hauptpatent beschriebenen Eigenschaften.179 parts of lactyl-p-aminophenol are dissolved in 300 parts of alcohol and 121 parts of allyl bromide are added. A solution of 56 parts of caustic potash in 200 parts of alcohol is then added and the mixture is refluxed for 48 hours. It then filtered from the precipitated potassium bromide from distilled most of the "alcohol and the residue is treated with water The resulting Laktyl-p -. # Iminophenolallylätlier solidified crystalline and wiid recrystallized from water It has the characteristics described in the main patent..

Beispiel 3. Example 3.

157Teile Formyl-p-aininoph(,nol werden in 2oo Teilen Alkohol gelöst und mit 121 Teilen Allylbromid. versetzt. Unter Kochen am Rückfluß gibt man in mehreren Portionen 56Teile Atzkali in 2co Teilen Alkohol gelöst 1,inzu. Nach zwei Stunden filtriert man vom Bromkali ab und verdampft den Alkohol bis auf einen kleinen Teil. Das zu ückbleibende 01 erstarrt beim Eingießen in Wasser. Man kristallisiert au,; Wasser um und erhält den Formylp-aminophenolallylätlier in weißen Blättchen vom , ##Z, #, -#,4u13 te- #> 4 4;r; i! -1 , 4. 142 Teile Acet-p-aiiiin(,plieiiol Werd(-i' In 2oo Teilen Alkohol gelöst und Mit 76,5 Teilen Allylchlorid ve-setzt. Man fügt dazu eine Lösung von 56 Teilen Atzkali in 2oo Teilen Alkohol und kocht am Rückflußkühler. Darauf filtriert man vom ausgeschiedenen Chlorkali ab, destilliert den größten Teil des Alkohols ab und versetzt den Rückstand mit Wasser, worauf der p-Acetaminophenolallyläther als rasch erstarrendes Öl ausfällt. - 157 parts of formyl-p-aininoph (, nol are dissolved in 2oo parts of alcohol and mixed with 121 parts of allyl bromide. 56 parts of caustic potash, dissolved in 2co parts of alcohol, are added in several portions while boiling under reflux. After two hours, the potassium bromide is filtered off off and the alcohol evaporates except for a small part. This solidifies to ückbleibende 01 when poured into water. crystallize au ,; water around and gets the Formylp-aminophenolallylätlier in white flakes from , ## Z, #, - #, 4u13 te- #> 4 4; r; i! -1, 4. 142 parts of acet-p-aiiiin (, plieiiol are dissolved in 2oo parts of alcohol and reacted with 76.5 parts of allyl chloride. A solution of 56 parts of caustic potash in 2oo parts of alcohol is added and the mixture is refluxed is filtered off from the precipitated Chlorkali distilled most of the alcohol and the residue is treated with water, whereupon the p-Acetaminophenolallyläther precipitates as rapidly solidifying oil. -

Claims (1)

PATETXT-ANSPRUCH: Abänderung des durch Patent 3io967 geschützten Verfahrens zür Darstellung von Acylderivaten eines p-Aminophenoläthers, dadurch gekennzeichnet, daß man hier die Acylderivate des p-Aminophenols mit einem Allyll)alogenid und Alkali behandelt.PATETXT CLAIM: Modification of the process protected by patent 3io967 for the preparation of acyl derivatives of a p-aminophenol ether, characterized in that that here the acyl derivatives of p-aminophenol with an allyll) alogenid and alkali treated.
DE1917332204D 1917-12-01 1917-12-01 Process for the preparation of acyl derivatives of a p-aminophenol ether Expired DE332204C (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE332204T 1917-12-01

Publications (1)

Publication Number Publication Date
DE332204C true DE332204C (en) 1921-01-22

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Family Applications (1)

Application Number Title Priority Date Filing Date
DE1917332204D Expired DE332204C (en) 1917-12-01 1917-12-01 Process for the preparation of acyl derivatives of a p-aminophenol ether

Country Status (1)

Country Link
DE (1) DE332204C (en)

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