DE923191C - Process for the preparation of 5-cycloalkylidene-pseudothiohydantoins - Google Patents
Process for the preparation of 5-cycloalkylidene-pseudothiohydantoinsInfo
- Publication number
- DE923191C DE923191C DEL14080A DEL0014080A DE923191C DE 923191 C DE923191 C DE 923191C DE L14080 A DEL14080 A DE L14080A DE L0014080 A DEL0014080 A DE L0014080A DE 923191 C DE923191 C DE 923191C
- Authority
- DE
- Germany
- Prior art keywords
- cycloalkylidene
- pseudothiohydantoins
- preparation
- general formula
- cycloalkyl
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung von 5-Cycloalkyliden-pseudothiohydantoinen Die Kondensation von. Pseudothiohydantoin mit aromatischen Aldehyden ist schon lange bekannt; sie führt zu 5-Ben.zyliden-pseu:dothiohydantoinen (vgl. z. B. F. Kucera, Monatshefte für Chemie, Bd. 35, Jahrgang 1914, S. 653).Process for the preparation of 5-cycloalkylidene-pseudothiohydantoins The condensation of. Pseudothiohydantoin with aromatic aldehydes has been around for a long time known; it leads to 5-benzylidene-pseu: dothiohydantoins (cf.e.g. F. Kucera, Monthly books for chemistry, vol. 35, year 1914, p. 653).
5-Cycloalkyliden-pseudothiohydantoine wurden noch nicht beschrieben. Es wurde nun gefunden, daß man 5-Cy cloalkyli:den-pseudothiobydantoine der allgemeinen Formel worin Y einen gegebenenfalls substituierten 2wertigen aliphatischen Rest mit mindestens 4 Kohlenstoffatomen, der mit dem außerhalb des Heteroringes stehenden Kohlenstoffatom zu einem Cycloalkylring geschlossen ,ist, bedeutet, herstellen kann, indem man ß, ß-Cycloalkyliden-Glycidester der allgemeinen Formel worin Y die gleiche Bedeutung hat wie oben und R einen niedrigmolekularen Alkylrest bedeutet, mit Thioharnstoff, zweckmäßig in einem Lösungsmittel innerhalb eines längeren Zeitraums, umsetzt und die entstandenen 5-(r'-Oxycycloalkyl)-pseudothlohydantoine mit einem dehydratisierenden Mittel behandelt. Dabei spielen sich die folgenden Reaktionen ab: Als Lösungsmittel sind brauchbar Alkohole, Eisessig, Dioxan u. dgl.5-Cycloalkylidene-pseudothiohydantoins have not yet been described. It has now been found that 5-Cy cloalkyli: den-pseudothiobydantoine of the general formula wherein Y is an optionally substituted divalent aliphatic radical with at least 4 carbon atoms, which is closed with the carbon atom outside the hetero ring to form a cycloalkyl ring, can be prepared by β, β-cycloalkylidene glycidate of the general formula where Y has the same meaning as above and R is a low molecular weight alkyl radical, reacted with thiourea, advantageously in a solvent within a relatively long period of time, and treated the 5- (r'-oxycycloalkyl) -pseudothlohydantoine with a dehydrating agent. The following reactions take place: Alcohols, glacial acetic acid, dioxane and the like can be used as solvents.
Die entstehenden Produkte sind wertvolle Zwischenprodukte für Phartnazeutioa und Farbstoffe und besitzen selbst beachtliche sedative Eigenschaften.The resulting products are valuable intermediate products for Phartnazeutioa and dyes and have considerable sedative properties themselves.
Beispiel 38 g Thioharnstoff werden in. 350 ccm Methanol gelöst und 96 g Pentamethylenglycidäthylester zugegeben. Die nach 3wöchigem Stehen abgeschiedenen Kristalle werden abgesaugt und mit Wasser ausgekocht. Durch Einengen der Mutterlauge, Auskochen des Rückstandes mit Wasser und Digerieren mit Äther erhält man eine weitere Menge der Substanz. Nach Umkristallisation aus Alkohol erhält man 26g 5-(i'-Oxycyclohexyl)-pseudoth,-iohydantoin, F. = 245°' (unter Zersetzung). io g davon werden 6 Stunden in Eisessig unter Rückfluß gehalten. Nach dem Erkalten wird das auskristallisierte Produkt abgesaugt. Man erhält 1,7 g 5-Cyclohexyliden - pseudothiohydantoin als hellgelbe Kristalle, F. = 252° (unter Zersetzung). Durch Einengere der Mutterlauge erhält man noch weitere Mengen des Produktes.EXAMPLE 38 g of thiourea are dissolved in 350 cc of methanol and 96 g of ethyl pentamethylene glycidate are added. The crystals separated out after standing for 3 weeks are filtered off with suction and boiled with water. A further amount of the substance is obtained by concentrating the mother liquor, boiling the residue with water and digesting with ether. After recrystallization from alcohol, 26 g of 5- (i'-oxycyclohexyl) -pseudoth, -iohydantoin, mp = 245 ° '(with decomposition) are obtained. 10 g of it are refluxed in glacial acetic acid for 6 hours. After cooling, the product which has crystallized out is filtered off with suction. 1.7 g of 5-cyclohexylidene-pseudothiohydantoin are obtained as pale yellow crystals, mp = 252 ° (with decomposition). More quantities of the product are obtained by reducing the amount of mother liquor.
Claims (1)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEL14080A DE923191C (en) | 1952-12-04 | 1952-12-04 | Process for the preparation of 5-cycloalkylidene-pseudothiohydantoins |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEL14080A DE923191C (en) | 1952-12-04 | 1952-12-04 | Process for the preparation of 5-cycloalkylidene-pseudothiohydantoins |
Publications (1)
Publication Number | Publication Date |
---|---|
DE923191C true DE923191C (en) | 1955-02-07 |
Family
ID=7259707
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DEL14080A Expired DE923191C (en) | 1952-12-04 | 1952-12-04 | Process for the preparation of 5-cycloalkylidene-pseudothiohydantoins |
Country Status (1)
Country | Link |
---|---|
DE (1) | DE923191C (en) |
-
1952
- 1952-12-04 DE DEL14080A patent/DE923191C/en not_active Expired
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