DE903817C - Process for the preparation of derivatives of 1-phenyl-2,3-dimethyl-4-amino-5-pyrazolone - Google Patents
Process for the preparation of derivatives of 1-phenyl-2,3-dimethyl-4-amino-5-pyrazoloneInfo
- Publication number
- DE903817C DE903817C DET11A DET0000011A DE903817C DE 903817 C DE903817 C DE 903817C DE T11 A DET11 A DE T11A DE T0000011 A DET0000011 A DE T0000011A DE 903817 C DE903817 C DE 903817C
- Authority
- DE
- Germany
- Prior art keywords
- phenyl
- amino
- dimethyl
- pyrazolone
- derivatives
- 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
- 238000000034 method Methods 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims description 3
- RLFWWDJHLFCNIJ-UHFFFAOYSA-N 4-aminoantipyrine Chemical class CN1C(C)=C(N)C(=O)N1C1=CC=CC=C1 RLFWWDJHLFCNIJ-UHFFFAOYSA-N 0.000 title description 2
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 5
- 238000006386 neutralization reaction Methods 0.000 claims description 4
- 239000012433 hydrogen halide Substances 0.000 claims description 3
- 229910000039 hydrogen halide Inorganic materials 0.000 claims description 3
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 claims description 3
- 150000001242 acetic acid derivatives Chemical class 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 229940051880 analgesics and antipyretics pyrazolones Drugs 0.000 claims description 2
- 235000011056 potassium acetate Nutrition 0.000 claims description 2
- 230000001476 alcoholic effect Effects 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- KEVMYFLMMDUPJE-UHFFFAOYSA-N 2,7-dimethyloctane Chemical group CC(C)CCCCC(C)C KEVMYFLMMDUPJE-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical group CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 150000003014 phosphoric acid esters Chemical class 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical group CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 description 1
- 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
- KKUKTXOBAWVSHC-UHFFFAOYSA-N Dimethylphosphate Chemical compound COP(O)(=O)OC KKUKTXOBAWVSHC-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000001754 anti-pyretic effect Effects 0.000 description 1
- 239000002221 antipyretic Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 235000019658 bitter taste Nutrition 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000001784 detoxification Methods 0.000 description 1
- -1 di (n) hutyl Chemical group 0.000 description 1
- 125000006003 dichloroethyl group Chemical group 0.000 description 1
- UCQFCFPECQILOL-UHFFFAOYSA-N diethyl hydrogen phosphate Chemical compound CCOP(O)(=O)OCC UCQFCFPECQILOL-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- HWJHWSBFPPPIPD-UHFFFAOYSA-N ethoxyethane;propan-2-one Chemical compound CC(C)=O.CCOCC HWJHWSBFPPPIPD-UHFFFAOYSA-N 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 210000004013 groin Anatomy 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000011833 salt mixture Substances 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-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
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
- C07F9/6503—Five-membered rings
- C07F9/65031—Five-membered rings having the nitrogen atoms in the positions 1 and 2
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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Verfahren zur Herstellung von Derivaten des 1-Phenyl-2, 3-dimethyl-4-amino-5-pyrazolons Bekanntlich läßt sich im i-Phenyl-2, 3ldimethylq.-a#m,ino-5-pyrazolon die antipyretisehe Wirkung durch Alkyl.ierung steigern.Process for the preparation of derivatives of 1-phenyl-2,3-dimethyl-4-amino-5-pyrazolone It is known that in i-phenyl-2,3ldimethylq.-a # m, ino-5-pyrazolone the antipyretic Increase effect through alkylation.
Es wurde nun gefunden, daß man diese Steigerung noch übertreffen kann, wenn man in an sich bekannter Weise das i-Phenyl-2, 3-dimethyl-4-amino-5-pyrazolon in :die entsprechenden Diaralkyl- bzw. Dialkylphosphorsäureesterderivate überführt unter Herstellung einer N-P-Bindung. Die Herstellung der neuen Derivate des i-Phenyl-2, 3-dimethyl-d.-amino-5-pyrazolons erfolgt erfindungsgemäß dadurch, daß man auf i-Phenyl-2, 3-dimethyl-q.-amino-5-pyrazolon Monohalogenverbindungen von Dialkyl- bzw. Diaralkylphosphorsäureestern unter Neutralisation des gebildeten Halogenwasserstoffs einwirken läßt. Zur Neutralisation des Halogenwasserstoffs dienen vorzugsweise Alkaliacetate, wie Kaliumacetate in Methanol, oder tertiäre Basen, wie Pyridin oder T'riäthylamin. Auch ein zweites Äquivalent des i-Phenyl-2, 3-dimethyl-4.-amino-5-pyrazolons kann als Halogenw asserstoffacceptor verwendet werden. Der besondere Vorteil der neuen Verbindungen liegt darin, daß ihre Esternatur durch Verseifung die Ausscheidung und damit die Entgiftung ermöglicht im Gegen,s.atz zu den bisher verwendeten N-Di-alkyl-Derivaten.It has now been found that this increase can still be exceeded, if in a known manner the i-phenyl-2,3-dimethyl-4-amino-5-pyrazolone into: the corresponding diaralkyl or dialkyl phosphoric acid ester derivatives forming an N-P bond. The production of the new derivatives of i-phenyl-2, 3-dimethyl-d.-amino-5-pyrazolones is carried out according to the invention by using i-phenyl-2, 3-dimethyl-q.-amino-5-pyrazolone monohalogen compounds of dialkyl or diaralkyl phosphoric acid esters allowed to act with neutralization of the hydrogen halide formed. For neutralization of the hydrogen halide are preferably used alkali acetates, such as potassium acetates in Methanol or tertiary bases such as pyridine or triethylamine. Also a second Equivalent of i-phenyl-2, 3-dimethyl-4.-amino-5-pyrazolons can be used as halogen hydrogen acceptor be used. The particular advantage of the new compounds is that their ester nature enables excretion and thus detoxification through saponification in contrast, see sentence on the previously used N-di-alkyl derivatives.
Beispiel i io,i5 g i-Phenyl-2, 3-dimethyl-q.-amino-5-pyrazolon werden mit 7,25g Dimethylphosphorsäureesterchlorid in Anwesenheit einer Lösung von 8,2 g Natriumacetat und 2,8 g Ätzkali in Methanol umgesetzt. Nach beendeter Umsetzung beträgt das pH des Reaktionsgemisches 7,0 bis 7,2. Das gebildete Halogenalkalisalzgemisch wird entfernt und die Lösung eingeengt. Durch Animpfen kristallisiert der gebildete i - Phenyl - 2, 3 -dimethyl -4-am-ino-5-pyrazolon-N-phosphorsäured@imethylester aus. Die Reinigung erfolgt durch Umkristallisieren; das Produkt kristallisiert beispielsweise aus einem Aceton-Äther-Gemisch in farblosen Kristallen. welche nach sorgfältigem Trocknen den Schmelzpunkt 186 bis 187' besitzen. Die Verbindung ist sowohl in Wasser wie in den gebräuchlichen organischen Lösungsmitteln löslich.Example io, i5 g of i-phenyl-2,3-dimethyl-q.-amino-5-pyrazolone are reacted with 7.25 g of dimethylphosphoric acid ester chloride in the presence of a solution of 8.2 g of sodium acetate and 2.8 g of caustic potash in methanol. After the reaction has ended, the pH of the reaction mixture is 7.0 to 7.2. The resulting haloalkali salt mixture is removed and the solution is concentrated. The i-phenyl-2,3-dimethyl -4-am-ino-5-pyrazolone-N-phosphoric acid @ imethyl ester formed crystallizes out by seeding. The purification is carried out by recrystallization; the product crystallizes, for example, from an acetone-ether mixture in colorless crystals. which, after careful drying, have a melting point of 186 to 187 '. The compound is soluble in both water and common organic solvents.
Beispiel 2 1O,15 g i-Phenyl-2, 3-dimethyl-4-ami.no-5-pyrazolon werden in Acetonlösung mit 4,32 g Diäthylphosphorsäureesterchlorid umgesetzt. Das i-Phenyl-2, 3-.dimethyl-4-arriino-5-pyrazolonhydrochlorid kristallisiert aus und wird erbfiltriert. Die eingeengte Mutterlauge wird durch Animpfen zur Kristallisation gebracht.Example 2 10.15 g of i-phenyl-2, 3-dimethyl-4-ami.no-5-pyrazolone reacted in acetone solution with 4.32 g of diethylphosphoric acid ester chloride. The i-phenyl-2, 3-dimethyl-4-arriino-5-pyrazolone hydrochloride crystallizes out and is filtered off. The concentrated mother liquor is made to crystallize by inoculation.
Die farblose kristallisierte Verbindung von bitterem Geschmack zeigte einen Schmp. von 122°. Sie ist leicht löslich in Wasser, sehr leicht löslich auch in Alkoholen, Methylenchlorid, Chloroform, Aceton, Acetonitril und Dioxan. In Benzol, Essigester, Tetrahydrofuran und Tetrachlorkohlenstoff löst sie sich gut. Äther, Petroläther und Ligroin lösen praktisch nicht. Schwefelkohlenstoff löst sehr schwer.The colorless crystallized compound showed a bitter taste a melting point of 122 °. It is easily soluble in water, and also very easily soluble in alcohols, methylene chloride, chloroform, acetone, acetonitrile and dioxane. In benzene, It dissolves well in ethyl acetate, tetrahydrofuran and carbon tetrachloride. Ether, Petroleum ether and ligroin practically do not dissolve. Carbon disulfide is very difficult to dissolve.
In entsprechender Weise sind die Diisopropyl-, Di(n) hutyl-, Diisoamyl-, Dichloräthyl- .und Dihenzylphosphorsäüreesterderivate herstellbar.In a corresponding manner, the diisopropyl, di (n) hutyl, diisoamyl, Dichloroethyl and dihenzylphosphoric acid ester derivatives can be produced.
Das Dipropylderivat fällt in farblosen, glänzenden, stark verfilzten Nädelchen vom Schmp. i 16° an. Es ist in Wasser leicht löslich, ebenso in organischen Lösungsmitteln. Die Löslichkeit des Dipropylclerivats in Äther und Ligroin ist gegenüber dem Diäthvlderivat erhöht. Das Dibutvlderivat fällt zunächst in stark verfilzten Nädelchen aus, die sich beim Stehen zu derben, kurzen. Nädelchen umlagern und einen Schmp. von i i i bis 112° aufweisen. Das Dibutylderivat löst sich im Gegensatz zum Diäthyl- und Dipropylderiv at nur noch gering in Wasser, wohl aber in verdünnter Salzsäure, und bildet hierbei eine farblose Lösung. In organischen Lösungsmitteln ist das Dibutylderivat leicht löslich, Äther und Li.groin lösen Dias Dibutylderivat wesentlich leichter als das Diäthyl- und Dipropyliderivat.The dipropyl derivative falls in colorless, glossy, heavily matted Needles from the melting point i 16 °. It is easily soluble in water, as well as in organic ones Solvents. The solubility of the Dipropylclerivats in ether and ligroin is opposite the diethvlderivat increased. The dibutvl derivative initially falls into heavily matted Small needles that become coarse when standing, short. Move needles and one Have a melting point of i i i to 112 °. The dibutyl derivative dissolves in contrast to Diethyl and dipropyl derivative only slightly in water, but in more dilute form Hydrochloric acid, and forms a colorless solution. In organic solvents the dibutyl derivative is easily soluble, ether and Li.groin dissolve the dibutyl derivative much lighter than the diethyl and dipropylide derivatives.
Das Di-isoamylderivat kristallisiert in weißen, wachsartigen Nadeln vom Schmp. 89 bis 9i°. Es löst sich wenig in Wasser, hingegen in Methanol, Äthanol, Essigester, Äther, Chloroform, Benzol sowie in Essigsäure. In Petroläther ist es nicht löslich.The di-isoamyl derivative crystallizes in white, waxy needles with a melting point of 89 to 91 °. It dissolves little in water, but in methanol, ethanol, ethyl acetate, ether, chloroform, benzene and acetic acid. It is not soluble in petroleum ether.
Claims (3)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DET11A DE903817C (en) | 1949-10-06 | 1949-10-06 | Process for the preparation of derivatives of 1-phenyl-2,3-dimethyl-4-amino-5-pyrazolone |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DET11A DE903817C (en) | 1949-10-06 | 1949-10-06 | Process for the preparation of derivatives of 1-phenyl-2,3-dimethyl-4-amino-5-pyrazolone |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE903817C true DE903817C (en) | 1954-02-11 |
Family
ID=7542824
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DET11A Expired DE903817C (en) | 1949-10-06 | 1949-10-06 | Process for the preparation of derivatives of 1-phenyl-2,3-dimethyl-4-amino-5-pyrazolone |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE903817C (en) |
-
1949
- 1949-10-06 DE DET11A patent/DE903817C/en not_active Expired
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