DE923191C - Process for the preparation of 5-cycloalkylidene-pseudothiohydantoins - Google Patents

Process for the preparation of 5-cycloalkylidene-pseudothiohydantoins

Info

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
Application number
DEL14080A
Other languages
German (de)
Inventor
Heinz Dr Schubert
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 DEL14080A priority Critical patent/DE923191C/en
Application granted granted Critical
Publication of DE923191C publication Critical patent/DE923191C/en
Expired legal-status Critical Current

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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

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  • 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)

PATENTANSPRUCH: Verfahren zur Herstellung von 5-Cycloalkyliden-pseudothiohydantoinen der allgemeinen Formel worin Y einen gegebenenfalls substituierten 2wertigen abiphatischen Rest mit mindestens 4 Kohlenstoffatomen, der mit dem außerhalb des Heteroringes stehenden Kohlenstoffatom zu einem Cycloalkylring geschlossen ist, bedeutet, dadurch gekennzeichnet, daß man ß, ß-Cycloalkyl-ndenglyci,dester .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-(i'-Oxycycloalkyl) -pseudothiohydantoine mit einem dehydratisierenden Mittel behandelt.PATENT CLAIM: Process for the preparation of 5-cycloalkylidene-pseudothiohydantoins of the general formula wherein Y is an optionally substituted divalent abiphatic radical with at least 4 carbon atoms, which is closed with the carbon atom outside the hetero ring to form a cycloalkyl ring, characterized in that β, ß-cycloalkyl-ndene glyci, dester .der 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- (i'-oxycycloalkyl) -pseudothiohydantoine with a dehydrating agent.
DEL14080A 1952-12-04 1952-12-04 Process for the preparation of 5-cycloalkylidene-pseudothiohydantoins Expired DE923191C (en)

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)

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