DE924864C - Process for the preparation of thiourea pellets - Google Patents
Process for the preparation of thiourea pelletsInfo
- 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
Links
- 238000000034 method Methods 0.000 title claims description 3
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 title description 12
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 title description 6
- 238000002360 preparation method Methods 0.000 title description 2
- 239000008188 pellet Substances 0.000 title 1
- 150000002148 esters Chemical class 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- OJGMBLNIHDZDGS-UHFFFAOYSA-N N-Ethylaniline Chemical compound CCNC1=CC=CC=C1 OJGMBLNIHDZDGS-UHFFFAOYSA-N 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 150000003585 thioureas Chemical class 0.000 description 3
- WUBBRNOQWQTFEX-UHFFFAOYSA-N 4-aminosalicylic acid Chemical compound NC1=CC=C(C(O)=O)C(O)=C1 WUBBRNOQWQTFEX-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 2
- 229960004909 aminosalicylic acid Drugs 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000010792 warming Methods 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 1
- 244000052616 bacterial pathogen Species 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000008164 mustard oil Substances 0.000 description 1
- MLPVBIWIRCKMJV-UHFFFAOYSA-N o-aminoethylbenzene Natural products CCC1=CC=CC=C1N MLPVBIWIRCKMJV-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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)
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 |
Family
ID=7084410
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)
| 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 |
| EP0049538A3 (en) * | 1979-07-14 | 1982-10-13 | Bayer Ag | Use of thioureum derivatives as medicaments in the treatment of lipoid metabolism diseases |
-
1950
- 1950-11-12 DE DEF5018A patent/DE924864C/en not_active Expired
Cited By (2)
| 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 |
| 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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