DE571038C - Process for the preparation of a compound from 4-dimethylamino-1-phenyl-2,3-dimethyl-5-pyrazolone and p-aminobenzoic acid isobutyl ester - Google Patents

Process for the preparation of a compound from 4-dimethylamino-1-phenyl-2,3-dimethyl-5-pyrazolone and p-aminobenzoic acid isobutyl ester

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Publication number
DE571038C
DE571038C DER79814D DER0079814D DE571038C DE 571038 C DE571038 C DE 571038C DE R79814 D DER79814 D DE R79814D DE R0079814 D DER0079814 D DE R0079814D DE 571038 C DE571038 C DE 571038C
Authority
DE
Germany
Prior art keywords
dimethyl
pyrazolone
phenyl
dimethylamino
aminobenzoic acid
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
Application number
DER79814D
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German (de)
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DR BAPTIST REUTER
Original Assignee
DR BAPTIST REUTER
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Publication date
Application filed by DR BAPTIST REUTER filed Critical DR BAPTIST REUTER
Priority to DER79814D priority Critical patent/DE571038C/en
Application granted granted Critical
Publication of DE571038C publication Critical patent/DE571038C/en
Expired legal-status Critical Current

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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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

Verfahren zur Darstellung einer Verbindung aus 4-Dimethylamino-1-phenyl-2,3-dimethyl-5-pyrazolon und p-Aminobenzoesäureisobutylester Im Patent 569 616 wurde gezeigt, daß das 4-Dimethylamino-i-phenyl-a, 3-dimethyl-5-pyrazolon sich mit p-Aminobenzoesäureäthylester zu einer neuen chemischen Verbindung mit therapeutisch wertvollen Eigenschaften vereinigt.Process for the preparation of a compound from 4-dimethylamino-1-phenyl-2,3-dimethyl-5-pyrazolone and p-aminobenzoic acid isobutyl ester In the patent 569 616 it was shown that the 4-dimethylamino-i-phenyl-a, 3-dimethyl-5-pyrazolone with p-aminobenzoic acid ethyl ester to a new chemical Combination with therapeutically valuable properties.

Es wurde gefunden, daß auch der p-Aminobenzoesäureisobuty lester beim Zusammenschmelzen mit 4-Dimethylamino-i-phenyl-2, 3-dimethyl-5-pyrazolon oder beim Erhitzen mit Lösungen desselben sich zu einem neuen einheitlichen Produkt vereinigt. Dasselbe kann aus organischen Lösungsmitteln umgelöst werden, ohne seine Zusammensetzung oder den Schmelzpunkt zu ändern. Das neue Produkt schmilzt bei 73°, während der Schmelzpunkt des p-Aminobenzoesäureisobutylesters bei 63 bis 65° und der des 4-Dimethylaminoi-phenyl-2, 3-dimethyl-5-pyrazolons bei io8° liegt. Ein mechanisches Gemisch beider schmilzt von 53 bis 9o°..It has been found that the p-aminobenzoic acid isobuty lester with Melting together with 4-dimethylamino-i-phenyl-2, 3-dimethyl-5-pyrazolone or at Heating with solutions of the same combine to form a new unitary product. It can be redissolved from organic solvents without changing its composition or to change the melting point. The new product melts at 73 ° during the Melting point of isobutyl p-aminobenzoate at 63 to 65 ° and that of 4-dimethylaminoi-phenyl-2, 3-dimethyl-5-pyrazolones is at 10 °. A mechanical mixture of the two melts from 53 to 9o ° ..

Auch diese Verbindung ist therapeutisch wertvoll, besonders bei schmerzhaften Magenstörungen usw. Sie ist leicht löslich in Alkohol und Benzol, schwer löslich in Ligroin und Wasser.This connection is also therapeutically valuable, especially when it is painful Stomach disorders, etc. It is easily soluble in alcohol and benzene, but not very soluble in ligroin and water.

Beispiele 1. 193 g p-Aminobenzoesäureisobutylester und 23i g 4-Diinethylamino-i-phenyl-2, 3-dimethyl-5-pyrazolon werden zusammengeschmolzen. Die erkaltete Schmelze erstarrt zu Kristallen, die aus Alkohol- oder Äther umkristallisiert werden. F. 73.Examples 1. 193 g of isobutyl p-aminobenzoate and 23i g of 4-diinethylamino-i-phenyl-2, 3-dimethyl-5-pyrazolone are melted together. The cooled melt solidifies to crystals that are recrystallized from alcohol or ether. F. 73.

2. 193 g p-Aminobenzoesäureisobutylester und 231 g 4-Dimethylamino-i-phenyl-2, 3-dimethyl-5-pyrazolon werden mit 5oo g Alkohol 1f2 Stunde am Rückflußkühler gekocht; i Teil des Alkohols wird im Vakuum entfernt und die Masse erkalten gelassen.. Das umkristallisierte Produkt wird abgesaugt, mit etwas Äther gewaschen und im Vakuum getrocknet.2. 193 g of isobutyl p-aminobenzoate and 231 g of 4-dimethylamino-i-phenyl-2,3-dimethyl-5-pyrazolone are refluxed with 500 g of alcohol for 1f2 hours; Part of the alcohol is removed in vacuo and the mass is allowed to cool. The recrystallized product is filtered off with suction, washed with a little ether and dried in vacuo.

Claims (1)

PATE NTAIN'SP1tUCFi: Abänderung des durch Patent 569 616 geschützten Verfahrens zur Darstellung einer Verbindung aus 4.-Dimethylaminoi-phenyl-2, 3-dimethyl-5-pyrazolon und p-Aminobenzoesäureisobutylester, darin bestehend, daß man hier je i Mol. 4-Dimethylamino-i-phenyl-2, 3-dimethyl-5-pyrazolon und p-Aminobenzoesäureisobutylester entweder zusammenschmilzt und die Schmelze zerkleinert und gegebenenfalls umlöst oder das äquimolekulare Gemisch der Ausgangsstoffe in Lösungsmitteln unmittelbar erhitzt und dann auskristallisieren läßt. PATE NTAIN'SP1tUCFi: Modification of the process protected by patent 569 616 for the preparation of a compound of 4-dimethylaminoiphenyl-2, 3-dimethyl-5-pyrazolone and p-aminobenzoic acid isobutyl ester, consisting in that one mol. 4 Dimethylamino-i-phenyl-2, 3-dimethyl-5-pyrazolone and isobutyl p-aminobenzoate either melts together and the melt is crushed and possibly redissolved or the equimolecular mixture of the starting materials is heated immediately in solvents and then allowed to crystallize.
DER79814D 1929-11-16 1929-11-16 Process for the preparation of a compound from 4-dimethylamino-1-phenyl-2,3-dimethyl-5-pyrazolone and p-aminobenzoic acid isobutyl ester Expired DE571038C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DER79814D DE571038C (en) 1929-11-16 1929-11-16 Process for the preparation of a compound from 4-dimethylamino-1-phenyl-2,3-dimethyl-5-pyrazolone and p-aminobenzoic acid isobutyl ester

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DER79814D DE571038C (en) 1929-11-16 1929-11-16 Process for the preparation of a compound from 4-dimethylamino-1-phenyl-2,3-dimethyl-5-pyrazolone and p-aminobenzoic acid isobutyl ester

Publications (1)

Publication Number Publication Date
DE571038C true DE571038C (en) 1933-02-23

Family

ID=7416138

Family Applications (1)

Application Number Title Priority Date Filing Date
DER79814D Expired DE571038C (en) 1929-11-16 1929-11-16 Process for the preparation of a compound from 4-dimethylamino-1-phenyl-2,3-dimethyl-5-pyrazolone and p-aminobenzoic acid isobutyl ester

Country Status (1)

Country Link
DE (1) DE571038C (en)

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