CH191237A - Process for the preparation of omega-methylsulfonic acids of primary or secondary pyrazolone amines. - Google Patents
Process for the preparation of omega-methylsulfonic acids of primary or secondary pyrazolone amines.Info
- Publication number
- CH191237A CH191237A CH191237DA CH191237A CH 191237 A CH191237 A CH 191237A CH 191237D A CH191237D A CH 191237DA CH 191237 A CH191237 A CH 191237A
- Authority
- CH
- Switzerland
- Prior art keywords
- omega
- acids
- primary
- preparation
- amines
- Prior art date
Links
- 239000002253 acid Substances 0.000 title claims description 11
- 238000000034 method Methods 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims description 4
- 150000007513 acids Chemical class 0.000 title description 9
- -1 pyrazolone amines Chemical group 0.000 title description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 5
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 3
- OBESRABRARNZJB-UHFFFAOYSA-N aminomethanesulfonic acid Chemical class NCS(O)(=O)=O OBESRABRARNZJB-UHFFFAOYSA-N 0.000 description 3
- 150000004982 aromatic amines Chemical class 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 229940098779 methanesulfonic acid Drugs 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical compound O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000003799 water insoluble solvent Substances 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Verfahren zur Darstellung von omega-Methylsulfonsäuren primärer oder sekundärer Pyr azolonamine. Bekanntlich entstehen durch Einwirkung von Aldehyden und schwefliger Säure auf aromatische Amine die omega-Alkylsulfon- säuren aromatischer Amine. Man hat die gleichen Säuren aus den durch Kondensation aromatischer Amine mit Aldehyden und Al kalibisulfit entstehenden Alkalisalzen der omega-Aminomethansulfonsäuren durch An säuern gewonnen.
Die Abtrennung dieser Säuren ist trotz ihrer grossen Zersetzlichkeit durch ihre Unlöslichkeit oder Schwerlöslich keit in Wasser ermöglicht. Bei der Über tragung der genannten Verfahren auf die Amine der Pyrazolonreibe konnten bisher die omega-Methansulfonsäuren nicht isoliert wer den. Die omega-Aminoalkylsulfonsäuren die ser Reihe sind in Wasser ausserordentlich löslich und zersetzen sich bereits kurz nach dem Ansäuern der Lösungen ihrer Salze, was durch den Geruch von schwefliger Säure er kennbar ist. In dem.
Patent Nr. 184875 ist ein Ver fahren zur Darstellung von -omega-Methyl- sulfonsäuren primärer oder sekundärer Pyra-- zolonamine durch Umsetzung der Pyrazolon- amine mit Formaldehyd und schwefliger Säure beschrieben, bei welchem man die Umsetzung in Gegenwart eines organischen Lösungsmit tels und bei einem Wassergehalt des Reak- tionsgemisches von höchstens 5 % ausführt. Es wurde nun gefunden,
dass man in gleich vorteilhafter Weise zu den genannten Sulfon- säuren gelangen kann, wenn man die Salze der entsprechenden Aminomethylsulfonsäuren in Gegenwart von organischen Lösungsmit teln und bei Anwesenheit von höchstens ge ringen Mengen Wasser ansäuert.
Die Salze der Aminomethylsulfonsäuren lassen sich aus den entsprechenden Aminen mit Formaldehyd und Bisulfitalkali in be kannter Weise darstellen (siehe z. B. deutsche Patentschrift Nr. 421505). Es können so die gleichen Methansulfonsäuren von Pyrazolon- aminen hergestellt werden und hierbei die gleichen organischen Lösungsmittel Verwen dung finden, die in dein Patent Nr. 184875 aufgeführt sind.
Jedoch kann bei der ITm- setzung der methansulfonsauren Salze mit Mineralsäure auch in Gegenwart eines nicht wasserlöslichen Lösungsmittels und in völli ger Abwesenheit von Wasser gearbeitet wer den.
Die nach dem neuen Verfahren erhältli chen Aminomethansulfonsäuren sollen zur Darstellung neuer Heilmittel Verwendung finden. <I>Beispiel:</I> 35 g 1-Phenyl-2,3-dimethyl-4-methylarnino- 5-pyrazolon-4-methansrrlfonsaures Natrium werden in 200 cm3 absolutem oder 96 %igem Alkohol verteilt und mit 100 <RTI
ID="0002.0025"> g einer 3,6 %igen alkoholischen Salzsäure versetzt, die aus ab solutem oder 96 0%igem Alkohol hergestellt ist. Nach erfolgter Umsetzung wird filtriert, wobei nach kurzer Zeit die entsprechende Methansulfonsäure auskristallisiert. Zerset zungspunkt 131-132 0 C.
Process for the preparation of omega-methylsulfonic acids of primary or secondary pyrazolonamines. It is known that the action of aldehydes and sulphurous acid on aromatic amines gives rise to the omega-alkylsulphonic acids of aromatic amines. The same acids have been obtained from the alkali salts of the omega-aminomethanesulfonic acids formed by condensation of aromatic amines with aldehydes and alkali metal sulfite by acidifying.
The separation of these acids is made possible by their insolubility or poor solubility in water despite their high decomposition. When transferring the above processes to the amines of the pyrazolone grater, the omega-methanesulfonic acids could not be isolated so far. The omega-aminoalkylsulfonic acids of this series are extremely soluble in water and decompose shortly after the acidification of the solutions of their salts, which can be recognized by the smell of sulphurous acid. By doing.
Patent No. 184875 is a process for the preparation of -omega-methylsulfonic acids of primary or secondary pyrazolonamines by reacting the pyrazolonamines with formaldehyde and sulfurous acid, in which the reaction is carried out in the presence of an organic solvent and with the water content of the reaction mixture does not exceed 5%. It has now been found
that the sulphonic acids mentioned can be obtained in an equally advantageous manner if the salts of the corresponding aminomethylsulphonic acids are acidified in the presence of organic solvents and in the presence of at most small amounts of water.
The salts of aminomethylsulfonic acids can be prepared in a known manner from the corresponding amines with formaldehyde and bisulfital potassium (see, for example, German Patent No. 421505). In this way, the same methanesulfonic acids can be produced from pyrazolonamines using the same organic solvents that are listed in patent no.
However, when the methanesulfonic acid salts are converted with mineral acid, it is also possible to work in the presence of a water-insoluble solvent and in the complete absence of water.
The aminomethanesulfonic acids obtainable according to the new process are to be used to represent new remedies. <I> Example: </I> 35 g of 1-phenyl-2,3-dimethyl-4-methylamino-5-pyrazolone-4-methanesulfonic acid are distributed in 200 cm3 of absolute or 96% alcohol and mixed with 100 <RTI
ID = "0002.0025"> g of a 3.6% alcoholic hydrochloric acid, which is made from absolute or 96 0% alcohol. After the reaction has taken place, it is filtered, the corresponding methanesulfonic acid crystallizing out after a short time. Decomposition point 131-132 0 C.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE191237X | 1934-01-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH191237A true CH191237A (en) | 1937-06-15 |
Family
ID=5727786
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH191237D CH191237A (en) | 1934-01-13 | 1935-01-08 | Process for the preparation of omega-methylsulfonic acids of primary or secondary pyrazolone amines. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH191237A (en) |
-
1935
- 1935-01-08 CH CH191237D patent/CH191237A/en unknown
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