CH97752A - Process for the preparation of 1-phenyl-2,3-dimethyl-4-dimethylamino-5-pyrazolone. - Google Patents
Process for the preparation of 1-phenyl-2,3-dimethyl-4-dimethylamino-5-pyrazolone.Info
- Publication number
- CH97752A CH97752A CH97752DA CH97752A CH 97752 A CH97752 A CH 97752A CH 97752D A CH97752D A CH 97752DA CH 97752 A CH97752 A CH 97752A
- Authority
- CH
- Switzerland
- Prior art keywords
- pyrazolone
- dimethyl
- phenyl
- dimethylamino
- preparation
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 7
- RMMXTBMQSGEXHJ-UHFFFAOYSA-N Aminophenazone Chemical compound O=C1C(N(C)C)=C(C)N(C)N1C1=CC=CC=C1 RMMXTBMQSGEXHJ-UHFFFAOYSA-N 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 6
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 3
- 235000019253 formic acid Nutrition 0.000 claims description 3
- RLFWWDJHLFCNIJ-UHFFFAOYSA-N 4-aminoantipyrine Chemical compound CN1C(C)=C(N)C(=O)N1C1=CC=CC=C1 RLFWWDJHLFCNIJ-UHFFFAOYSA-N 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000006200 ethylation reaction Methods 0.000 description 2
- 230000011987 methylation Effects 0.000 description 2
- 238000007069 methylation reaction Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- -1 1 - phenyl - 2,3 - dimethyl - 4 - amino-5-pyrazolone formaldehyde Chemical compound 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000006203 ethylation Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000012022 methylating agents Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/44—Oxygen and nitrogen or sulfur and nitrogen atoms
- C07D231/46—Oxygen atom in position 3 or 5 and nitrogen atom in position 4
- C07D231/48—Oxygen atom in position 3 or 5 and nitrogen atom in position 4 with hydrocarbon radicals attached to said nitrogen atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
Verfahren zur Darstellung von 1-Phenyl-2.3-dimethyl-4-dimethylamino-5-Pyrazolon. Gegenstand der vorliegenden Erfindung ist ein Verfahren zur Darstellung von 1-Phe- nyl - 2;3 - dimethy 1- 4 - dimethylamino - 5 - pyra- zolon, welches darin besteht, dass man auf 1- Phenyl - 2,3- dimethyl - 4 - amino-5-pyrazolon Formaldehyd bei Gegenwart von Ameisen säure einwirken lässt.
Gegenüber den andern bekannten 1VIethy- lierungsvorschriften für 1-Phenyl-2,3-dime- thyl-4-amino-5-pyrazolon hat das neue Ver fahren den Vorteil, dass es neben einer bes seren Ausbeute ein reineres, namentlich sehr wenig gefärbtes NIethylierungsprodukt liefert. Das Verfahren ist auch einfach durchzufüh ren. Es kann ohne Druck in offenen Gefässen mit einem billigen Methylierungsmittel gear beitet werden.
Die Ausführung des Verfahrens kann beispielsweise wie folgt geschehen 130 Teile Formaldebyd 30 o/oig werden mit 67 Teilen Ameisensäure 80 o/oig in einem emaillierten Rührkessel bis zum Kochen er hitzt. In diese stets itn Kochen erhaltene Flüssigkeit lässt man unter gutem Umrüh ren im Verlauf von 10 Stunden eine warme Lösung von 100 Teilen 1-Phenyl-2,3-di- methyl-4-amirro-5-pyrazolon in 150 Teilen Wasser zulaufen. Nach dem Einlaufen wird noch eine Stunde weiter erhitzt, wobei durch das Aufhören der Kohlensäureentwicklung das Ende der lblethylierung angezeigt wird.
Der überschüssige Formaldehyd kann am abstei genden Kühler als sehr verdünnte Lösung teil weise wieder gewonnen werden. Dem 14Iethy- lierungsgemisch, welches etwas abgekühlt wird, wird das 1-Pherryl-2,3-dimethyl-4-di- metlrylamino-5-pyrazolon durch Ausrühren mit 3-400 Teilen Benzol unter Zusatz von über schüssiger Natronlauge entzogen. Der aus der Benzollösung durch Abdestillieren erhaltene Kristallbrei ist wenig gefärbt.
Zur weiteren Reinigung erfolgt eine Kristallisation aus einem geeigneten Lösungsmittel, wie Benzol oder Al- kohl. Die Ausbeute an reinem 1-Phenyl-2,3- dimethyl-4-dimethylamino-5-pyrazolon beträgt 90 /o der berechneten Menge.
Process for the preparation of 1-phenyl-2,3-dimethyl-4-dimethylamino-5-pyrazolone. The present invention relates to a process for the preparation of 1-phenyl - 2; 3 - dimethy 1- 4 - dimethylamino - 5 - pyrazolone, which consists in that one on 1 - phenyl - 2,3 - dimethyl - 4 - amino-5-pyrazolone formaldehyde in the presence of formic acid.
Compared to the other known 1-ethylation regulations for 1-phenyl-2,3-dimethyl-4-amino-5-pyrazolone, the new method has the advantage that, in addition to a better yield, it is a purer, namely very little colored, methylation product supplies. The process is also easy to carry out. It can be worked with a cheap methylating agent in open vessels without pressure.
The process can be carried out, for example, as follows: 130 parts of 30% formaldehyde are heated to the boil with 67 parts of 80% formic acid in an enamelled stirred kettle. A warm solution of 100 parts of 1-phenyl-2,3-dimethyl-4-amirro-5-pyrazolone in 150 parts of water is allowed to run into this liquid, which is always kept boiling, with thorough stirring over the course of 10 hours. After running in, heating is continued for another hour, the end of the methylation being indicated by the cessation of the evolution of carbonic acid.
The excess formaldehyde can partly be recovered as a very dilute solution on the descending cooler. The 1-pherryl-2,3-dimethyl-4-dimethylamino-5-pyrazolone is removed from the ethylation mixture, which is cooled somewhat, by stirring with 3-400 parts of benzene with the addition of excess sodium hydroxide solution. The crystal pulp obtained from the benzene solution by distillation is not very colored.
For further purification, crystallization takes place from a suitable solvent, such as benzene or alcohol. The yield of pure 1-phenyl-2,3-dimethyl-4-dimethylamino-5-pyrazolone is 90% of the calculated amount.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH97752T | 1921-11-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH97752A true CH97752A (en) | 1923-02-16 |
Family
ID=4355528
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH97752D CH97752A (en) | 1921-11-23 | 1921-10-04 | Process for the preparation of 1-phenyl-2,3-dimethyl-4-dimethylamino-5-pyrazolone. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH97752A (en) |
-
1921
- 1921-10-04 CH CH97752D patent/CH97752A/en unknown
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