DE306938C - - Google Patents
Info
- Publication number
- DE306938C DE306938C DENDAT306938D DE306938DA DE306938C DE 306938 C DE306938 C DE 306938C DE NDAT306938 D DENDAT306938 D DE NDAT306938D DE 306938D A DE306938D A DE 306938DA DE 306938 C DE306938 C DE 306938C
- Authority
- DE
- Germany
- Prior art keywords
- glycolic acid
- glycolyl
- water
- ethers
- parts
- 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.)
- Active
Links
- AEMRFAOFKBGASW-UHFFFAOYSA-N glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 claims description 20
- -1 glycolyl para-aminophenol ethers Chemical class 0.000 claims description 12
- 150000008064 anhydrides Chemical class 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 4
- 238000009835 boiling Methods 0.000 description 3
- HMXHUUDRVBXHBQ-UHFFFAOYSA-N (2-hydroxyacetyl) 2-hydroxyacetate Chemical compound OCC(=O)OC(=O)CO HMXHUUDRVBXHBQ-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- MZJWIVHTYMCLDJ-UHFFFAOYSA-N (4-aminophenyl) 2-hydroxyacetate Chemical class NC1=CC=C(OC(=O)CO)C=C1 MZJWIVHTYMCLDJ-UHFFFAOYSA-N 0.000 description 1
- OYHOCUAXXOWENX-UHFFFAOYSA-N 2-hydroxy-N-(2-hydroxyphenyl)acetamide Chemical compound OCC(=O)NC1=CC=CC=C1O OYHOCUAXXOWENX-UHFFFAOYSA-N 0.000 description 1
- PJFNNMFXEVADGK-UHFFFAOYSA-N 2-hydroxy-N-phenylacetamide Chemical compound OCC(=O)NC1=CC=CC=C1 PJFNNMFXEVADGK-UHFFFAOYSA-N 0.000 description 1
- BHAAPTBBJKJZER-UHFFFAOYSA-N P-Anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 1
- 229920000954 Polyglycolide Polymers 0.000 description 1
- 241000218998 Salicaceae Species 0.000 description 1
- 230000001754 anti-pyretic Effects 0.000 description 1
- 239000002221 antipyretic Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- ZANNOFHADGWOLI-UHFFFAOYSA-N ethyl 2-hydroxyacetate Chemical compound CCOC(=O)CO ZANNOFHADGWOLI-UHFFFAOYSA-N 0.000 description 1
- 230000002349 favourable Effects 0.000 description 1
- 125000000350 glycoloyl group Chemical group O=C([*])C([H])([H])O[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 150000005217 methyl ethers Chemical group 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000002035 prolonged Effects 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
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
Es wurde gefunden, daß man die Glykolyl-paminophenoläther in vorzüglicher Ausbeute,und Reinheit durch Erhitzen der p-Aminophenoläther mit den Anhydriden der Glykolsäure er-S hält. Als Anhydride der Glykolsäure sind hier sowohl das Glykolid vom Schmelzpunkt 86° als auch das Polyglykolid vom Schmelzpunkt 223 ° aufzufassen, desgleichen aber auch das Produkt, welches man durch Erhitzen von Glykolsäure auf etwa 200 bis 250 ° erhält. Letzteres stellt ein in Wasser unlösliches kristallinisches Pulver dar, welches sich bei längerer Berührung mit 'Wasser wieder in Glykolsäure zurückverwandelt.It has been found that the glycolyl paminophenol ethers in excellent yield and purity by heating the p-aminophenol ethers with the anhydrides of glycolic acid he-S holds. As anhydrides of glycolic acid are here both glycolide with a melting point of 86 ° and polyglycolide with a melting point 223 °, but also the product obtained by heating Glycolic acid to about 200 to 250 °. The latter constitutes a crystalline one that is insoluble in water Powder, which is converted back into glycolic acid after prolonged contact with water.
An Stelle der erwähnten Anhydride der Glykolsäure kann man sich mit gleichem Er- · folge auch der Ester derselben bedienen.Instead of the mentioned anhydrides of glycolic acid, one can use the same also follow the esters of the same serve.
Des Glykolids bedienten sich bereits B i s c h 0 f f und Waiden zur Darstellung von Glykölsäureanilid (Annalen 279, 49).Glycolide has already been used by B i s c h 0 f f and willows for the representation of glycolic acid anilide (Annalen 279, 49).
Die Glykolyl-p-aminophenyläther wurden schon von Böttinger (Arch. d. Ph. 234, 159) durch Erhitzen der Aminophenoläther mit Glykolsäure dargestellt; bei diesem Verfahren entsteht indes kein einheitliches Produkt; Böttinger erhielt keine reinen-Verbindungen, wie die von ihm angegebenen Schmelzpunkte zeigen. Die Ausbeute an. reinem Glykolylaminophenoläther ist so bedeutend ungünstigerThe glycolyl p-aminophenyl ethers were already from Böttinger (Arch. d. Ph. 234, 159) by heating the aminophenol ethers with Glycolic acid shown; However, this process does not result in a uniform product; Böttinger did not receive any pure compounds like the melting points given by him demonstrate. The yield at. pure glycolylaminophenol ether is so significantly less favorable
als nach dem neuen Verfahren. ' " ■than under the new procedure. '"■
Die Glykolyl - ρ - aminophenoläther, insbesondere der Methyl- und Äthyläther, wurden als vorzügliche Antipyretica erkannt.The glycolyl - ρ - aminophenolethers, especially the methyl and ethyl ethers, were recognized as excellent antipyretics.
1. Darstellung von Glykolyl-ρ-phenetidin aus Glykolsäureanhydrid und ρ - Phenetidin: Ein Gemenge \ von 100 Teilen Glykolsäureanhydrid (erhalten durch Erhitzen von Glycolsäure auf 230° bis zum Unlöslichwerden in Wasser) und 240 Teilen Paraphenetidin wird im ölbad so lange auf etwa 130 ° erhitzt, bis die anfangs flüssige Schmelze erstarrt. Das Reaktionsprodukt wird aus siedendem Wasser umkristallisiert. Man erhält so das Glykolylp-phenetidin in farblosen, bei 153 ° schmelzenden Kristallen, löslich in etwa 650 Teilen kalten Wassers, reichlich löslich in: heißem Wasser und kochendem Alkohol, sehr leicht in Aceton, dagegen sehr schwer in Äther, Benzol und Chloroform. -1. Preparation of glycolyl-ρ-phenetidine from glycolic anhydride and ρ - phenetidine: A mixture of 100 parts of glycolic anhydride (obtained by heating glycolic acid to 230 ° until it becomes insoluble in water) and 240 parts of paraphenetidine heated in an oil bath to about 130 ° until the initially liquid melt solidifies. The reaction product is made from boiling water recrystallized. The glycolylp-phenetidine is thus obtained in colorless form, melting at 153 ° Crystals, soluble in about 650 parts of cold water, freely soluble in: hot water and boiling alcohol, very light in acetone, on the other hand very heavy in ether, benzene and Chloroform. -
Ersetzt man in obigem Beispiel das Paraphenetidin durch die entsprechende Menge Paraanisidin, so erhält man bei unverändertem Verfahren das 'bei ioi° schmelzende Glykolylp-anisidin, welches sich durch noch bedeutend größere Wasserlöslichkeit auszeichnet.In the above example, if you replace the paraphenetidine with the appropriate amount Paraanisidine, with unchanged procedure one obtains the glycolyl p-anisidine which melts at ioi °, which is characterized by an even greater solubility in water.
2. Darstellung von Glykolyl-p-phenetidin aus einem Glykolsäureester und Paraphenetidin : Ein Gemenge von 135 Teilen Paraphenetidin und 100 Teilen Glykolsäureäthylester (oder der entsprechenden Menge eines anderen Glykolsäureesters) wird auf 150 bis 200° erhitzt, solange n,och Alkohol entweicht und bis eine Probe beim Erkalten kristallinisch erstarrt. Das Reaktionsprodukt wird aus2. Preparation of glycolyl-p-phenetidine from a glycolic acid ester and paraphenetidine : A mixture of 135 parts of paraphenetidine and 100 parts of ethyl glycolate (or the equivalent amount of another glycolic acid ester) is increased to 150 to Heated to 200 ° as long as alcohol escapes and until a sample becomes crystalline on cooling stiffens. The reaction product becomes off
siedendem Wasser umkristallisiert und ist identisch· rnjt dem im ersten Beispiel beschriebenen., l: /recrystallized from boiling water and is identical to that described in the first example., l: /
In, glejcher Weise erhält man aus einem beliebigen Glykolsäureester und Paraanisidin das(bei/ioi° schmelzende Glykolyl-p-anisidin.In, glejcher manner, from any Glykolsäureester Paraanisidin and the (at / ioi ° melting glycolyl-p-anisidine.
Claims (1)
Verfahren zur Darstellung von Glykolylpara-aminophenoläthern, dadurch gekennzeichnet, daß -man Paraaminophenoläther in der Wärme auf Anhydride oder Ester der Glykolsäure einwirken läßt.Patent claim:
Process for the preparation of glycolyl para-aminophenol ethers, characterized in that para-aminophenol ethers are allowed to act on anhydrides or esters of glycolic acid in the heat.
Publications (1)
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Country Status (1)
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