DE280225C - - Google Patents
Info
- Publication number
- DE280225C DE280225C DENDAT280225D DE280225DA DE280225C DE 280225 C DE280225 C DE 280225C DE NDAT280225 D DENDAT280225 D DE NDAT280225D DE 280225D A DE280225D A DE 280225DA DE 280225 C DE280225 C DE 280225C
- Authority
- DE
- Germany
- Prior art keywords
- parts
- alcohol
- derivatives
- aminophenol
- acetyl
- 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
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-Aminophenol Chemical class NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 claims description 4
- 150000001298 alcohols Chemical class 0.000 claims description 4
- 230000000875 corresponding Effects 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 150000008064 anhydrides Chemical class 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 150000005215 alkyl ethers Chemical class 0.000 claims 1
- 150000002170 ethers Chemical class 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 238000002844 melting Methods 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- RZVAJINKPMORJF-UHFFFAOYSA-N p-acetaminophenol Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 4
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 3
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-Chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 2
- SSZWWUDQMAHNAQ-UHFFFAOYSA-N 3-MCPD Chemical compound OCC(O)CCl SSZWWUDQMAHNAQ-UHFFFAOYSA-N 0.000 description 2
- CPJSUEIXXCENMM-UHFFFAOYSA-N Phenacetin Chemical class CCOC1=CC=C(NC(C)=O)C=C1 CPJSUEIXXCENMM-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 230000001476 alcoholic Effects 0.000 description 2
- 230000000202 analgesic Effects 0.000 description 2
- 230000001754 anti-pyretic Effects 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 2
- 239000001103 potassium chloride Substances 0.000 description 2
- 235000011164 potassium chloride Nutrition 0.000 description 2
- 235000011118 potassium hydroxide Nutrition 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229960000583 Acetic Acid Drugs 0.000 description 1
- -1 Acetyl-p-aminophenol glycerol Chemical compound 0.000 description 1
- 229940040526 Anhydrous Sodium Acetate Drugs 0.000 description 1
- 229960003893 Phenacetin Drugs 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000005354 acylalkyl group Chemical group 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- FFLYUXVZEPLMCL-UHFFFAOYSA-N ethylchloranuidyl formate Chemical compound CC[Cl-]OC=O FFLYUXVZEPLMCL-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N oxane Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 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
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
- JVe 280225 KLASSE 12 o. GRUPPE- JVe 280225 CLASS 12 or GROUP
FARBENFABRIKEN vorm. FRIEDR. BAYER & CO. in LEVERKUSEN b. CÖLN.FARBENFABRIKEN vorm. FRIEDR. BAYER & CO. in LEVERKUSEN b. COLOGNE.
In der Phenacetinreihe sind bisher in der Alkylgruppe hydroxylierte Derivate der O-alkylierten, N-acylierten p-Aminophenole nicht beschrieben worden. Die bis jetzt bekannten Präparate zeigen neben einer geringen analgetischen Wirkung hauptsächlich antipyretische Eigenschaften.In the phenacetin series there are so far hydroxylated derivatives of the O-alkylated, N-acylated p-aminophenols are not has been described. The preparations known up to now show not only a low analgesic effect Mainly antipyretic properties.
Es wurde nun die bemerkenswerte Feststellung gemacht, daß durch Einführung von ίο einer oder mehreren Oxygruppen in das O-Alkylradikal der p-Acylaminophenole der Formel:The remarkable observation has now been made that by introducing ίο one or more oxy groups in the O-alkyl radical of the p-acylaminophenols of the formula:
Acyl·Acyl
C6H4-OR1 C 6 H 4 -OR 1
(R = H, Alkyl, Acyl, Aryl und Aralkyl;
R1= Oxalkyl)(R = H, alkyl, acyl, aryl and aralkyl;
R 1 = oxalkyl)
Körper mit vollständig anderer Wirkung entstehen. Die antipyretische Wirkung tritt nämlieh gegenüber der analgetischen in ganz auffallender Weise zurück. Außerdem wirken diese neuen Derivate des p-Aminophenols weniger hämoglobinbildend als Phenacetin. Sie haben daher ganz erhebliches medizinisches Interesse.Bodies emerge with a completely different effect. The antipyretic effect occurs compared to the analgesic in a very striking way. In addition, these new derivatives of p-aminophenol are less effective hemoglobin-forming as phenacetin. You therefore have very considerable medical issues Interest.
Die neuen Körper werden gewonnen durch Verätherung der p-Acylaminophenole mit mehrwertigen Alkoholen oder deren Anhydriden oder durch Umsetzung der p-Acylaminophenole mit den entsprechenden halogensubstituierten Alkoholen, wie Glykolchlorhydrin, Monochlorhydrin usw., oder durch Acylierung von den entsprechenden Oxyderivaten der O-alkylierten p-Aminophenole in der Aminogruppe.The new bodies are obtained by etherification of the p-acylaminophenols with polyhydric alcohols or their anhydrides or by reacting the p-acylaminophenols with the corresponding halogen-substituted alcohols, such as glycol chlorohydrin, monochlorohydrin, etc., or by acylation of the corresponding oxy derivatives of the O-alkylated p-aminophenols in the amino group.
3535
Zu einer Lösung von 100 Teilen Acetyl-paminophenol in 300 Teilen Alkohol wird eine Lösung von 42 Teilen Ätzkali (85 prozentig) in 40 Teilen Wasser zugegeben. Man erhitzt diese alkoholische Lösung zum Sieden, fügt nach und nach 75 Teile a-Monochlorhydrin in 100 Teilen Alkohol hinzu und kocht noch einige Stunden am Rückflußkühler. Nach Absaugen des ausgeschiedenen Chlorkaliums und Abdampfen des Alkohols wird das Reaktionsprodukt aus Alkohol umkristallisiert. Man erhält so farblose Kristalle vom Schmelzpunkt 138 °, die in Wasser und Alkohol löslich sind.To a solution of 100 parts of acetyl-paminophenol in 300 parts of alcohol is a solution of 42 parts of caustic potash (85 percent) in 40 parts of water were added. This alcoholic solution is heated to the boil, after which and after 75 parts of a-monochlorohydrin in 100 parts Add alcohol and reflux for a few hours. After suctioning off the excreted Potassium chloride and evaporation of the alcohol, the reaction product is recrystallized from alcohol. Colorless crystals are obtained in this way with a melting point of 138 °, which are soluble in water and alcohol.
Zu einer Lösung von 150 Teilen Acetyl-paminophenol in 450 Teilen Alkohol wird eine Lösung von 63 Teilen Ätzkali (85 prozentig) in 60 Teilen Wasser hinzugegeben. Zur siedenden alkoholischen Flüssigkeit wird eine Lösung von 86 Teilen Glykolchlorhydrin in 150 Teilen Alkohol zugetropft und einige Stunden am Rückfiußkühler gekocht. Das ausgeschiedene Chlorkalium wird abgesaugt und der Alkohol ab-To a solution of 150 parts of acetyl-paminophenol in 450 parts of alcohol, a solution of 63 parts of caustic potash (85 percent) in 60 parts of water is added. To the boiling alcoholic liquid is a solution of 86 parts of glycol chlorohydrin in 150 parts of alcohol added dropwise and boiled for a few hours on the reflux condenser. The excreted potassium chloride is sucked off and the alcohol
gedampft. Das stark gefärbte Reaktionsprodukt läßt sich aus Alkohol gut Umkristallisieren. Der hierbei erhaltene Acetylaminophenöläther ist in Wasser und Alkohol löslich und bildet farblose Kristalle vom Schmelzpunkt 120 °.steamed. The strongly colored reaction product can easily be recrystallized from alcohol. The acetylaminophen oil ether obtained in this way is soluble in water and alcohol and forms colorless crystals with a melting point of 120 °.
150 Teile Acetyl-p-aminophenol und 44 Teile Äthylenoxyd werden 10 Stunden im geschlossenen Rohr auf 150° erhitzt. Das Reaktionsprodukt wird aus Alkohol umkristallisiert und liefert den Acetyl-p-aminophenolglykoläther in Form farbloser Kristalle vom Schmelzpunkt 120150 parts of acetyl-p-aminophenol and 44 parts Ethylene oxide is heated to 150 ° in a closed tube for 10 hours. The reaction product is recrystallized from alcohol and supplies the acetyl-p-aminophenol glycol ether in Form of colorless crystals with a melting point of 120
100 Teile Acetyl-p-aminophenol, 200 Teile Glycerin und 100 Teile wasserfreies Natriumacetat werden 15 Stunden lang auf 200 bis 210 ° erhitzt. Der Rückstand wird mit Wasser ausgewaschen und aus Alkohol umkristallisiert. Man erhält so den Acetyl-p-aminophenolglycerinäther in Form farbloser Kristalle vom Schmelzpunkt 138 °.100 parts of acetyl-p-aminophenol, 200 parts of glycerin and 100 parts of anhydrous sodium acetate are heated to 200 to 210 ° for 15 hours. The residue is washed out with water and recrystallized from alcohol. Acetyl-p-aminophenol glycerol ether is obtained in this way in the form of colorless crystals with a melting point of 138 °.
200 Teile Acetyl-p-aminophenolglykoläther vom Schmelzpunkt 120° werden in einem Gemisch von 150 Teilen Pyridin und 5000 Teilen Aceton gelöst und zu der Lösung langsam unter Rühren 150 Teile Chlorameisensäureäthylester zugefügt. Nach beendeter Reaktion wird die Flüssigkeit mit Wasser verdünnt und das sich ausscheidende rohe Urethan des Acetyl-p-aminophenolglykoläthers aus Benzol umkristallisiert. Das reine Produkt bildet farblose Kristalle vom Schmelzpunkt 104 °.200 parts of acetyl-p-aminophenol glycol ether melting point 120 ° are in a mixture of 150 parts of pyridine and 5000 parts Dissolved acetone and slowly adding 150 parts of ethyl chloroformate to the solution with stirring added. After the reaction has ended, the liquid is diluted with water and that is Excreting crude urethane of acetyl-p-aminophenolglycolether recrystallized from benzene. The pure product forms colorless crystals with a melting point of 104 °.
250 Teile 2 · 4-Dinitrophenyl-p-aminophenolglykoläther vom Schmelzpunkt 128 ° der Formel: 250 parts of 2x4-dinitrophenyl-p-aminophenol glycol ether with a melting point of 128 ° of the formula:
NO8-NO 8 -
-NH-NO9 -NH-NO 9
OC2H4OHOC 2 H 4 OH
werden in 1500 Teilen Eisessig gelöst und die Lösung etwa 1 Stunde lang auf 70 "erwärmt. Die Reaktionsflüssigkeit wird mit Wasser verdünnt und der ausgeschiedene 2 · 4-Dinitrophenylacetyl-p-aminophenolglykoläther aus Alkohol' umkristallisiert.are dissolved in 1500 parts of glacial acetic acid and the solution is heated to 70 "for about 1 hour. The reaction liquid is diluted with water and the 2 · 4-dinitrophenylacetyl-p-aminophenol glycol ether which has separated out is diluted recrystallized from alcohol.
Der neue Körper vom Schmelzpunkt 113° von der Formel:The new body with a melting point of 113 ° from the formula:
COCH3 COCH 3
-OC9H-OH-OC 9 H-OH
N0o-<N0o- <
XN02
bildet rotbraune Kristalle. X N0 2
forms red-brown crystals.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE280225C true DE280225C (en) |
Family
ID=536077
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT280225D Active DE280225C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE280225C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2538105A (en) * | 1948-06-29 | 1951-01-16 | Emerson Drug Company Of Baltim | Preparation of bromophenacetin |
-
0
- DE DENDAT280225D patent/DE280225C/de active Active
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2538105A (en) * | 1948-06-29 | 1951-01-16 | Emerson Drug Company Of Baltim | Preparation of bromophenacetin |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE814152C (en) | everkusen I Process for the production of esters of phosphoric acid and thiophosphoric acid | |
| DE1163850B (en) | Process for the production of new, non-ionic, skin-friendly derivatives of capillary-active tertiary amines | |
| DE2748722A1 (en) | PROCESS FOR MANUFACTURING AN AETHERSULFONATE | |
| DE3611302A1 (en) | FLUORINATED, MULTI-VALUE ALCOHOLS, METHOD FOR THEIR PRODUCTION AND THEIR USE | |
| DE1182671B (en) | Process for the production of new ethers and thioethers of panthenol | |
| DE280225C (en) | ||
| EP0067361B1 (en) | Process for the preparation of 2-alkoxy-(1,3)-dioxolanes | |
| DE2627985C3 (en) | 4-homoisotwistane-3-carboxylic acid ester and process for their preparation | |
| DE601822C (en) | Process for the preparation of ethers of the acetylene series | |
| EP0191385B1 (en) | Process for the preparation of thiocyanatomethylthiobenzothiazoles | |
| DE1570013B1 (en) | 1,4-bis (phenoxyacetyl) piperazine derivatives and processes for their preparation | |
| DE939507C (en) | Process for the preparation of bis (ª ‰ -chloraethyl) amines | |
| DE828105C (en) | Process for the production of bactericidal oil-soluble substances | |
| WO2006039974A1 (en) | Method for the production of monosubstituted piperazine derivatives | |
| DE2065698B2 (en) | Process for the preparation of 2-isopropyl-6-methyl-4 (3H) -pyrimidone | |
| DE1543332A1 (en) | Process for the preparation of anthranilic acid amides | |
| DE805757C (en) | Process for the production of acetylethylene oxide and diacetyl | |
| DE967826C (en) | Process for the production of aryloxyalkanol-sulfuric acid half-ester salts | |
| AT230863B (en) | Process for the preparation of dialkyl orthoformate amides | |
| DE869489C (en) | Process for the preparation of water-soluble compounds of acrylic acid and its ª ‡ or ª ‰ substitution products | |
| DE1022207B (en) | Process for the production of epoxy ethers | |
| DE1570013C (en) | 1,4 Bis (phenoxyacetyi) piperazinden vate and process for their preparation | |
| DE2744657A1 (en) | N-SUBSTITUTED ANILINE AND THEIR USE | |
| DE255305C (en) | ||
| DE2016597C (en) | Cyclopropanecarboxylic acid esters and their use as insecticides |