DE924864C - Process for the preparation of thiourea pellets - Google Patents

Process for the preparation of thiourea pellets

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Publication number
DE924864C
DE924864C DEF5018A DEF0005018A DE924864C DE 924864 C DE924864 C DE 924864C DE F5018 A DEF5018 A DE F5018A DE F0005018 A DEF0005018 A DE F0005018A DE 924864 C DE924864 C DE 924864C
Authority
DE
Germany
Prior art keywords
thiourea
oxy
phenyl
preparation
pellets
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
DEF5018A
Other languages
German (de)
Inventor
Walter Dr Aumueller
Gustav Dr Ehrhart
Heinrich Dr Ruschig
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Hoechst AG
Original Assignee
Hoechst AG
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Hoechst AG filed Critical Hoechst AG
Priority to DEF5018A priority Critical patent/DE924864C/en
Application granted granted Critical
Publication of DE924864C publication Critical patent/DE924864C/en
Expired legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C335/04—Derivatives of thiourea

Description

Verfahren zur Herstellung von Thioharnstoffabkömmlingen In der Patentschrift 848 040 ist die Herstellung von Thioharnstoffderivaten der p-Aminosalicylsäure beschrieben, die darin besteht, daß man Senföle mit p-Aminosalicylsäure oder ihren Derivaten umsetzt.Process for the preparation of thiourea derivatives In the patent specification 848 040 describes the production of thiourea derivatives of p-aminosalicylic acid, which consists in mixing mustard oils with p-aminosalicylic acid or its derivatives implements.

Es wurde gefunden, daß man Thioharnstoltderivate auch dadurch herstellen kann, daß man auf Ester des p-Carboxy-m-oxy-phenylsenföles sekundäre Basen einvirien laßt. It has been found that thiourestol derivatives can also be produced in this way It is possible that secondary bases are incorporated into esters of p-carboxy-m-oxy-phenyl mustard oil leaves.

Die Ester des p-Carboxy-m-oxy-phenylsenföles können beispielsweise durch direkte Umsetzung von Thioharnstoffen mit p-Aminosalicylsäureestern in der Wärme gewonnen werden. The esters of p-carboxy-m-oxy-phenyl mustard oil can, for example by direct reaction of thioureas with p-aminosalicylic acid esters in the Heat can be obtained.

Als sekundäre Basen kommen beispielsweise in Betracht: Methylanilin, Äthyl anilin, Piperidin, 5 Diäthylamin u. ä. As secondary bases, for example: methylaniline, Ethyl aniline, piperidine, 5 diethylamine and the like.

Die erhaltenen Verbindungen zeichnen sich durch eine starke Wirkung auf Tuberkelbazillen aus. The compounds obtained are characterized by a strong effect on tubercle bacilli.

Beispiel 1 N-Methyl-N-phenyl-N'-(p-carbomethoxy-m-oxyphenyl)-thioharnstoff 3 g Methylanilin werden mit 6,3 g feingepulvertem p-Carbomethoxy-m-oxy-phenylsenföl möglichst innig vermischt. Es tritt alsbald Erwärmung und völlige Erstarrung des. Gemisches ein. Der ReL aktionskuchen wird gepulvert, mit wenig kaltem Methanol digeriert und abgesaugt. Man erhält 8,3 g eines schon weitgehend reinen Rohproduktes. Zur weiteren Reinigung wird der rohe Thioharnstoff aus Äthanol umgelöst. F. = 140 bis 141°.Example 1 N-Methyl-N-phenyl-N '- (p-carbomethoxy-m-oxyphenyl) thiourea 3 g of methyl aniline are mixed as intimately as possible with 6.3 g of finely powdered p-carbomethoxy-m-oxy-phenyl mustard oil. Immediately warming and complete solidification of the mixture takes place. The reaction cake is powdered, digested with a little cold methanol and filtered off with suction. 8.3 g of an already largely pure crude product are obtained. For further purification, the crude thiourea is redissolved from ethanol. F. = 140 to 141 °.

Beispiel 2 N-Äthyl-N-phenyl-N'-(p-carboäthoxy-m-oxyphenyl)-thioharnstoff 6,7 g p-Carboäthoxy-m-oxy-phenylsenföl werden mit 3,6 g Monoäthylanilin durch gelindes Erwarmen zusammengeschmolzen. Beim Anreiben erstarrt die klare Schmelze zu einem festen Kristallkuchen, der gepulvert, mit wenig kaltem Methanol digeriert und abgesaugt wird. Man erhält 8,4 g eines weitgehend reinen Rohproduktes. Der reine Thioharnstoff der obigen Formel schmilzt nach dem Kristallisieren aus. Methanol bei 128°.Example 2 N-ethyl-N-phenyl-N '- (p-carboethoxy-m-oxyphenyl) thiourea 6.7 g of p-carboethoxy-m-oxy-phenyl mustard oil are melted together with 3.6 g of monoethylaniline by gentle heating. When rubbed, the clear melt solidifies to form a solid crystal cake, which is powdered, digested with a little cold methanol and filtered off with suction. 8.4 g of a largely pure crude product are obtained. The pure thiourea of the above formula melts out after crystallization. Methanol at 128 °.

Beispiel 3 N, N - Pentamethylen- N'- (p-carboäthoxy-m-oxyphenyl) -thioharnstoff 6,69 g p- Carboäthoxy-m-oxy-phenylsenföl und 2,55 g Piperidin werden zusammengegeben. Das Gemisch erwärmt sich und erstarrt zu einem festen Kristallkuchen. Man verreibt das Reaktionsprodukt mit kaltem Methanol, saugt abl und trocknet im Exsikkator. Die Ausbeute an rohem N, N-Pentamethylen - N'- (p-carboäthoxy - m-oxy-phenyl) - thioharnstoff beträgt 6,7 g. Zur weiteren Reinigung wird die Substanz aus Methanol und aus Eisessig umkristallisiert. F. = 160 bis 161°.Example 3 N, N - pentamethylene-N'- (p-carboethoxy-m-oxyphenyl) thiourea 6.69 g of p-carboethoxy-m-oxy-phenyl mustard oil and 2.55 g of piperidine are combined. The mixture heats up and solidifies to form a solid crystal cake. The reaction product is triturated with cold methanol, filtered off with suction and dried in a desiccator. The yield of crude N, N-pentamethylene-N'- (p-carboethoxy-m-oxy-phenyl) -thiourea is 6.7 g. For further purification, the substance is recrystallized from methanol and from glacial acetic acid. F. = 160 to 161 °.

Beispiel 4 N, N-Diäthyl-N'- (p-carbomethoxy-m-oxy-phenylthioharnstoff 1 g p-Carbomethoxy-m- oxy - phenylsenföl und 0,35 g Diäthylamin werden zusammengegeben. Es tritt Erwärmung auf. Man erhitzt noch kurze Zeit auf dem Dampfb'ad, läßt erkalten und behandelt mit kaltem Methanol. Die erhaltenen Kristalle werden abgesaugt und mit Methanol nachgewaschen.Example 4 N, N-Diethyl-N'- (p-carbomethoxy-m-oxy-phenylthiourea 1 g of p-carbomethoxy-m-oxy-phenyl mustard oil and 0.35 g of diethylamine are combined. Warming occurs. The mixture is heated for a short time on the steam bath, allowed to cool and treated with cold methanol. The crystals obtained are filtered off with suction and washed with methanol.

Die Ausbeute beträgt an rohem N, N-Diäthyl-N'- (p - carbomethoxy - m - oxy-phenyl) -thioharnstoff o,8g. Nach Umkristallisation aus Methanol beträgt der F.=970.The yield of crude N, N-diethyl-N'- (p - carbomethoxy - m - oxy-phenyl) -thiourea o, 8g. After recrystallization from methanol is the F. = 970.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung von Thicharnstoffabkömmlingen, dadurch gekennzeichnet, daß man Ester des p-Carboxy-m-oxy-phenylsenföles mit sekundären Basen umsetzt. PATENT CLAIM: Process for the production of thichurea derivatives, characterized in that esters of p-carboxy-m-oxy-phenyl mustard oil with secondary Bases.
DEF5018A 1950-11-12 1950-11-12 Process for the preparation of thiourea pellets Expired DE924864C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEF5018A DE924864C (en) 1950-11-12 1950-11-12 Process for the preparation of thiourea pellets

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEF5018A DE924864C (en) 1950-11-12 1950-11-12 Process for the preparation of thiourea pellets

Publications (1)

Publication Number Publication Date
DE924864C true DE924864C (en) 1955-04-21

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Family Applications (1)

Application Number Title Priority Date Filing Date
DEF5018A Expired DE924864C (en) 1950-11-12 1950-11-12 Process for the preparation of thiourea pellets

Country Status (1)

Country Link
DE (1) DE924864C (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0022958A1 (en) * 1979-07-14 1981-01-28 Bayer Ag Urea derivatives for use in the treatment of fat metabolism disorders
EP0049538A2 (en) * 1979-07-14 1982-04-14 Bayer Ag Use of thioureum derivatives as medicaments in the treatment of lipoid metabolism diseases

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0022958A1 (en) * 1979-07-14 1981-01-28 Bayer Ag Urea derivatives for use in the treatment of fat metabolism disorders
EP0049538A2 (en) * 1979-07-14 1982-04-14 Bayer Ag Use of thioureum derivatives as medicaments in the treatment of lipoid metabolism diseases
EP0049538A3 (en) * 1979-07-14 1982-10-13 Bayer Ag Use of thioureum derivatives as medicaments in the treatment of lipoid metabolism diseases

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