CH298403A - Process for the preparation of a phosphorus-containing derivative of m-aminophenols. - Google Patents
Process for the preparation of a phosphorus-containing derivative of m-aminophenols.Info
- Publication number
- CH298403A CH298403A CH298403DA CH298403A CH 298403 A CH298403 A CH 298403A CH 298403D A CH298403D A CH 298403DA CH 298403 A CH298403 A CH 298403A
- Authority
- CH
- Switzerland
- Prior art keywords
- phosphorus
- methyl
- diethyl
- aminophenols
- containing derivative
- Prior art date
Links
- CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical class NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 title claims description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 4
- 229910052698 phosphorus Inorganic materials 0.000 title claims description 4
- 239000011574 phosphorus Substances 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title description 2
- MESJRHHDBDCQTH-UHFFFAOYSA-N 3-(dimethylamino)phenol Chemical compound CN(C)C1=CC=CC(O)=C1 MESJRHHDBDCQTH-UHFFFAOYSA-N 0.000 claims description 4
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 claims description 3
- -1 m-dimethylaminophenyl diethyl phosphate methyl methyl sulfate Chemical compound 0.000 claims description 3
- PAIVEGSMGRDHOZ-UHFFFAOYSA-N [3-(dimethylamino)phenyl] diethyl phosphate Chemical compound CCOP(=O)(OCC)OC1=CC=CC(N(C)C)=C1 PAIVEGSMGRDHOZ-UHFFFAOYSA-N 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- UCQFCFPECQILOL-UHFFFAOYSA-N diethyl hydrogen phosphate Chemical compound CCOP(O)(=O)OCC UCQFCFPECQILOL-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000000155 melt Substances 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- JGSYKOGZFMBYAQ-UHFFFAOYSA-N CC[P]CC Chemical compound CC[P]CC JGSYKOGZFMBYAQ-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- LGTLXDJOAJDFLR-UHFFFAOYSA-N diethyl chlorophosphate Chemical compound CCOP(Cl)(=O)OCC LGTLXDJOAJDFLR-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/12—Esters of phosphoric acids with hydroxyaryl compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines phosphorhaltigen Abkömmlings von m-Amino-phenolen. Gegenstand des vorliegenden Patentes ist ein Verfahren zur Herstellung eines phosphor haltigen Abkömmlings von m-Amino-phenol, welches dadurch gekennzeichnet ist,
dass m- Dimethylaminophenol in Form eines Alkali metallderivates mit einem Diäthyl-phosphor- säur ehalogenid -umgesetzt und das erhaltene m - Dimethylamino - phenyl - diäthyl-phosphat mittels Dimethylsulfat in das m-Dimethyl amino-phenyl-diäthyl-phosphat-methyl-methyl- sulfat übergeführt wird.
Das m - Dimethylamino - phenyl - diäthyl- phosphat-methyl-methylsulfat schmilzt bei 101 bis 103 C.
Die neue Verbindung soll als Heilmittel verwendet werden.
<I>Beispiel:</I> 7,54 g (0,055M) m-Dimethylamino-phenol werden in einer Stickstoffatmosphäre einer aus 1,4 g (0,061 M) metallischem Natrium und 80 ems absolutem Äthanol gewonnenen Lösung von Natriiunäthylat zugesetzt. Zu der so erhaltenen alkoholischen Lösung des Natriumsalzes von m-Dimethylamino-phenol werden 10,51 g (0,061 M) Diäthylphosphor- säurechlorid auf einmal zugesetzt, und die Mi schung wird unter Rühren während 2 Stun den am Rückflusskühler erhitzt.
Nach Ab kühlung wird das ausgefallene Natriumchlorid abfiltriert und mit Alkohol ausgewaschen, worauf das Filtrat unter vermindertem Druck eingedampft wird. Das zurückbleibende Öl wird in etwa 50 cm3 Tetrachlorkohlenstoff gelöst, und die Lösung wird nacheinander mit wässriger Natronlauge (3 X 40 ems einer nor malen Lösung) und Wasser (3 X mit etwa 40 cm3) gewaschen, über Käliumcarbonat ge trocknet und dann unter vermindertem Druck eingedampft. Bei der Destillation unter 3 X 10-3 mm Hg geht der Rückstand bei 116 bis 120 C über.
Man erhält 10,9 g (- 73 % der Theorie) m-Diinethylamino-phenyl-diäthyl- phosphat von nD = 1,5112.
Eine Lösung von 6 g m-Dimethylamino- phenyl-diäthyl-phosphat, in 15 em3. trockenem Benzol und 3 em3 Dimethylsulfat wird wäh rend 48 Stunden stehen gelassen. Während dieser Zeit kristallisiert das Methyl-methylsul- fat aus. Nach Zusatz von Äther beläuft sich die Ausbeute auf 72 % der Theorie.
Durch Umkristallisieren aus einem Gemisch von Al kohol, Essigester und Äther erhält man<B>,</B> das m - Dimethylamino - phenyl - diäthyl - phosphat - methyl-methylsulfat vom Schmelzpunkt 101 bis 103 C.
Process for the preparation of a phosphorus-containing derivative of m-aminophenols. The subject of the present patent is a process for the production of a phosphorus-containing derivative of m-amino-phenol, which is characterized by
that m-dimethylaminophenol in the form of an alkali metal derivative is reacted with a diethyl phosphorus acid ehalide and the m-dimethylamino-phenyl-diethyl phosphate obtained is converted into m-dimethylamino-phenyl-diethyl-phosphate-methyl-methyl- sulfate is transferred.
The m - dimethylamino - phenyl - diethyl phosphate methyl methyl sulfate melts at 101 to 103 C.
The new compound is said to be used as a remedy.
<I> Example: </I> 7.54 g (0.055M) m-dimethylaminophenol are added in a nitrogen atmosphere to a solution of sodium ethylate obtained from 1.4 g (0.061M) metallic sodium and 80 ems absolute ethanol. 10.51 g (0.061 M) diethylphosphoric acid chloride are added all at once to the alcoholic solution of the sodium salt of m-dimethylaminophenol thus obtained, and the mixture is heated on the reflux condenser with stirring for 2 hours.
After cooling, the precipitated sodium chloride is filtered off and washed with alcohol, whereupon the filtrate is evaporated under reduced pressure. The remaining oil is dissolved in about 50 cm3 of carbon tetrachloride, and the solution is washed successively with aqueous sodium hydroxide solution (3 × 40 ems of a normal solution) and water (3 × with about 40 cm3), dried over potassium carbonate and then under reduced pressure evaporated. When distilling below 3 × 10-3 mm Hg, the residue passes over at 116 to 120.degree.
10.9 g (−73% of theory) of m-diinethylaminophenyl diethyl phosphate of nD = 1.5112 are obtained.
A solution of 6 g of m-dimethylaminophenyl diethyl phosphate in 15 em3. dry benzene and 3 em3 dimethyl sulfate is left to stand for 48 hours. During this time, the methyl methyl sulfate crystallizes out. After the addition of ether, the yield is 72% of theory.
Recrystallization from a mixture of alcohol, ethyl acetate and ether gives m-dimethylamino-phenyl-diethyl-phosphate-methyl-methyl sulfate with a melting point of 101 to 103 C.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB298403X | 1949-05-04 | ||
| CH282543T | 1950-04-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH298403A true CH298403A (en) | 1954-04-30 |
Family
ID=25732182
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH298403D CH298403A (en) | 1949-05-04 | 1950-04-27 | Process for the preparation of a phosphorus-containing derivative of m-aminophenols. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH298403A (en) |
-
1950
- 1950-04-27 CH CH298403D patent/CH298403A/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH354435A (en) | Process for the production of unsaturated carboxylic acids | |
| CH395967A (en) | Process for the preparation of racemic and optically active 2,3-dimercaptosuccinic acid | |
| CH298403A (en) | Process for the preparation of a phosphorus-containing derivative of m-aminophenols. | |
| CH298402A (en) | Process for the preparation of a phosphorus-containing derivative of m-aminophenols. | |
| AT99678B (en) | Process for the preparation of medicinally active mercury compounds. | |
| CH250806A (en) | Process for the preparation of a new oxyhydrophenanthrene derivative. | |
| DE958844C (en) | Process for the production of ª † -acyl-butyric acids | |
| CH183065A (en) | Process for the preparation of benzilic acid-2-diethylaminoethanol ester. | |
| CH347519A (en) | Process for the preparation of new, spasmolytically highly effective sulfonium salts | |
| DE1038548B (en) | Process for the preparation of ª ‡ -phenyl-ª ‰ -methyl-valeric acid | |
| CH81056A (en) | Process for the preparation of 2-phenylquinoline-4-carboxylic acid allyl ester | |
| CH243022A (en) | Process for the preparation of a basic ester. | |
| CH324086A (en) | Process for the preparation of α-dialkylamino-acetanilides | |
| CH281966A (en) | Process for the preparation of a heterocyclic carbamic acid derivative. | |
| CH306287A (en) | Process for the preparation of a piperidine derivative. | |
| CH377816A (en) | Process for the preparation of phosphonic acid esters | |
| CH242609A (en) | Process for the preparation of a new oxyhydrophenanthrene derivative. | |
| CH221847A (en) | Process for the preparation of calcium pantothenic acid. | |
| CH342210A (en) | Method for producing a local anesthetic | |
| CH297723A (en) | Process for the preparation of a new disubstituted nicotinic acid amide. | |
| CH251249A (en) | Process for the preparation of an acylated, aliphatic aminocarboxamide. | |
| CH282543A (en) | Process for the preparation of a phosphorus-containing derivative of an m-aminophenol. | |
| CH281656A (en) | Process for the preparation of a new imidazoline. | |
| CH244952A (en) | Process for the preparation of an acylated, aliphatic aminocarboxamide. | |
| CH221820A (en) | Process for the preparation of 2-methyl-3-carbethoxy-4-phenyl-5-cyano-dihydropyridone- (6). |