DEP0036250DA - Thiosemicarbazones - Google Patents
ThiosemicarbazonesInfo
- Publication number
- DEP0036250DA DEP0036250DA DEP0036250DA DE P0036250D A DEP0036250D A DE P0036250DA DE P0036250D A DEP0036250D A DE P0036250DA
- Authority
- DE
- Germany
- Prior art keywords
- thiosemicarbazones
- weight
- parts
- thiosemicarbazone
- aldehydes
- 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
- 229940042396 direct acting antivirals thiosemicarbazones Drugs 0.000 title claims description 8
- 150000003584 thiosemicarbazones Chemical class 0.000 title claims description 5
- -1 thiosemicarbazones cyclic aldehydes Chemical class 0.000 claims description 8
- 150000002576 ketones Chemical class 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- SRVJKTDHMYAMHA-WUXMJOGZSA-N thioacetazone Chemical compound CC(=O)NC1=CC=C(\C=N\NC(N)=S)C=C1 SRVJKTDHMYAMHA-WUXMJOGZSA-N 0.000 description 6
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 2
- 150000003583 thiosemicarbazides Chemical class 0.000 description 2
- GYRDZVHNPFBIST-UHFFFAOYSA-N (cyclohexylideneamino)thiourea Chemical compound NC(=S)NN=C1CCCCC1 GYRDZVHNPFBIST-UHFFFAOYSA-N 0.000 description 1
- VFVHWCKUHAEDMY-UHFFFAOYSA-N 2-chloro-5-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=C(Cl)C(C=O)=C1 VFVHWCKUHAEDMY-UHFFFAOYSA-N 0.000 description 1
- ZETIVVHRRQLWFW-UHFFFAOYSA-N 3-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=CC(C=O)=C1 ZETIVVHRRQLWFW-UHFFFAOYSA-N 0.000 description 1
- SKLUWKYNZNXSLX-UHFFFAOYSA-N 4-Acetamidobenzaldehyde Chemical compound CC(=O)NC1=CC=C(C=O)C=C1 SKLUWKYNZNXSLX-UHFFFAOYSA-N 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Description
Dr» Clemens lutter, Wuppertal, und Dr. Srnst Cauer, LeverkusenDr »Clemens Lutter, Wuppertal, and Dr. Srnst Cauer, Leverkusen
Kn/Sch Leverkusen, den Il0 Febr * 1949Kn / Sch Leverkusen, Il 0 February * 1949
Verfahren zur Herstellung von Thiosemicarbazone^Process for the preparation of Thiosemicarbazone ^
Vertreter der Thiosemioarbazone cyclischer Aldehyde stellen bekanntlich wertvolle therapeutische Produkte dar. Diese Verbindungen werden erhalten, indem man Thiosemicarbazide mit den entsprechenden cyclischen Aldehyden oder Derivaten dieser Aldehyde umsetzteRepresentatives of the thiosemioarbazones of cyclic aldehydes are known to be valuable therapeutic products. These compounds are obtained by combining thiosemicarbazides with the corresponding cyclic aldehydes or derivatives this reacted aldehydes
Es wurde nun gefunden^ daß man in völlig neuer Weis© zu Thiosemicarbaaonen cyclischer Aldehyde gelangen kann, wenn man Thiosemicarbazone von Zetonen jnit cyclischen Aldehyden umsetzt. Diese neue Seaktion besifztIu^a0' wegen der obenerwähnten Eigenschaften bestimmter Thiosemicarbazone cyclischer Aldehyde große technische Bedeutung0 Außerdem bietet sie gegenüber dem bisher angewendeten Verfahren zur Herstellung von Thiosemicarbazonen cyclischer Aldehyde Vorteile, da die Thiosemicarbazone von Ketonen leichter zugänglich sind als das bisher eingesetzte Thiosemicarbazide Die Thiosemicarbazone der Ketone lassen sich ZoBo in einfacher Ifeise durch Umsetzen von-Hydrazinrhodanid mit Ketonen in der Wärme herstellen (verglo ^frnmeldnng vnm glot-.It has now been found that thiosemicarbazones of cyclic aldehydes can be obtained in a completely new way if thiosemicarbazones of zetones are reacted with cyclic aldehydes. This new Seaktion besifztIu ^ a 0 'cyclic because of the above-mentioned properties of certain thiosemicarbazones aldehydes great industrial importance 0 In addition, it offers over the previously used method for producing thiosemicarbazones cyclic aldehydes advantages since the thiosemicarbazones are more accessible from ketones as the thiosemicarbazides previously used the thiosemicarbazone of ketones zobo can be easily Ifeise by reacting-Hydrazinrhodanid with ketones in the heat produced (verglo ^ frnmeldnng vnm glot-.
8S5 Gewichtsteile Aceton^iiosemicarbazon werden in 85 Gewichtsteilen 3o $iger Essigsäure gelöst und zusammen mit einer Lösung von 7? 5 GewichtBteilen Benzaldehyd==4~carbonsäure in 15o Gewichtsteilen Methanol kurze Zeit erwärmt0 Es scheidet sich das Thiosemicarbazon der Bensaldehyd=-4=carbonsäure ab, das nach dem Abkühlen in einer Ausbeute von 7?5 Gewichtsteilen isoliert Wird0 8 S 5 parts by weight of acetone iiosemicarbazone are dissolved in 85 parts by weight of 30% acetic acid and combined with a solution of 7? 5 GewichtBteilen benzaldehyde == 4 ~ carboxylic acid in 15o by weight of methanol heated briefly 0 It separates the thiosemicarbazone the Bensaldehyd = -4 = carboxylic acid from which is isolated, after cooling in a yield of 7? 5 parts by weight 0
In analoger Weise wird aus dem Acetoh-Thiosemicar-In an analogous manner, the Acetoh-Thiosemicar-
bazon mit m-Nitrobenzaldehyd das m-Uitrobenzal^ffhiosemicarbazon vom Schmelzpunkt 235°» mit p-Ithylsulfo&benzaldehyd das Thiosemicarbazon vom Schmelzpunkt 238°, mit 2-Chlor-5~nitrobenzaldshyd das Thiosemicarbazon vom Schmelzpunkt > 25o°, mit p-Ac©1pm'inobenzaldehyd das Thiosemicarbazon vom Schmelzpunkt 233° erhalten.bazon with m-nitrobenzaldehyde the m-uritrobenzal ^ ffhiosemicarbazon with melting point 235 ° »with p-ethylsulfo & benzaldehyde that Thiosemicarbazone with a melting point of 238 °, with 2-chloro-5-nitrobenzaldehyde the thiosemicarbazone with a melting point of> 25o °, with p-Ac © 1 pm'inobenzaldehyde, the thiosemicarbazone with a melting point of 233 ° is obtained.
3,4 Gewichtsteile Gyclohexanon-JThiosemicarbazon werden in 7o Gewichtsteilen 5o $iger Essigsäure heiß gelöst und mit einer Lösung von 3,2 Gewichtsteilen p-Acetaminobenz» aldehyd in 5o Gewichtsteilen Wasser einige Zeit zum Sieden erhitzt. Nach dem Erkalten werden durch Absaugen 3,6 Gewichtsteile des 4-Acetaminobenzal3^hiosemicarbazone erhalten. Schmelzpunkt nach der Umlösung aus Methanol-Hatronlaug® = 233°«3.4 parts by weight of cyclohexanone-thiosemicarbazone are dissolved in 70 parts by weight of 50% acetic acid while hot and boiling for some time with a solution of 3.2 parts by weight of p-acetaminobenzaldehyde in 50 parts by weight of water heated. After cooling, 3.6 parts by weight of 4-acetaminobenzal3 ^ hiosemicarbazone are obtained by suction. Melting point after redissolving from methanol-Hatronlaug® = 233 ° «
Claims (1)
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