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 etherInfo
- 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
- Authority
- 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
Links
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 title claims description 9
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 title claims description 7
- 125000002252 acyl group Chemical group 0.000 title claims description 7
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 4
- 239000003513 alkali Substances 0.000 claims description 2
- 230000004048 modification Effects 0.000 claims 1
- 238000012986 modification Methods 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 235000011118 potassium hydroxide Nutrition 0.000 description 3
- QFUINNIXZFOXBE-UHFFFAOYSA-N 1-(5-amino-2-hydroxyphenyl)-2-hydroxypropan-1-one Chemical compound C(C(O)C)(=O)C1=C(C=CC(=C1)N)O QFUINNIXZFOXBE-UHFFFAOYSA-N 0.000 description 1
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- -1 allyl halide Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
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
Landscapes
- 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
Claims (1)
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 |
Family
ID=6201807
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) |
-
1917
- 1917-12-01 DE DE1917332204D patent/DE332204C/en not_active Expired
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