DE1020339B - Process for the preparation of 3-amino-oxazolidonen- (2) - Google Patents

Process for the preparation of 3-amino-oxazolidonen- (2)

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Publication number
DE1020339B
DE1020339B DEE12151A DEE0012151A DE1020339B DE 1020339 B DE1020339 B DE 1020339B DE E12151 A DEE12151 A DE E12151A DE E0012151 A DEE0012151 A DE E0012151A DE 1020339 B DE1020339 B DE 1020339B
Authority
DE
Germany
Prior art keywords
amino
oxazolidonen
preparation
general formula
cyclized
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.)
Pending
Application number
DEE12151A
Other languages
German (de)
Inventor
Gabriel Gever
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.)
Warner Chilcott Pharmaceuticals Inc
Original Assignee
Norwich Pharmacal Co
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 Norwich Pharmacal Co filed Critical Norwich Pharmacal Co
Publication of DE1020339B publication Critical patent/DE1020339B/en
Pending legal-status Critical Current

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  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Description

Verfahren zur Herstellung von 3-Amino-oxazolidonen-(2) 3-Amino-oxazolidone-(2) der allgemeinen Formel in welcher R, R1, R2 und R3 Wasserstoff, niedere Alkyl-oder Oxyalkylreste bedeuten und gleich oder verschieden sein können, sind bisher noch nicht beschrieben worden. Sie sind als Zwischenprodukte zur Herstellung wertvoller Chemotherapeutika wichtig.Process for the preparation of 3-amino-oxazolidonen- (2) 3-amino-oxazolidone- (2) of the general formula in which R, R1, R2 and R3 denote hydrogen, lower alkyl or oxyalkyl radicals and can be identical or different have not yet been described. They are important as intermediates in the manufacture of valuable chemotherapeutic agents.

Es wurde nun gefunden, daß man 3-Amino-oxazolidone-(2) der angegebenen Formel in guter Ausbeute und Reinheit erhält, wenn man die Hydrochloride entsprechender ß-Oxyalkylsemicarbazide durch Behandlung mit Säuren unter Austritt von Ammoniak cyclisiert.It has now been found that 3-Amino-oxazolidone- (2) of the specified Formula is obtained in good yield and purity if the hydrochloride is used more appropriately ß-Oxyalkylsemicarbazide by treatment with acids with release of ammonia cyclized.

Das Verfahren der vorliegenden Erfindung wird durch das nachfolgende Beispiel erläutert.The method of the present invention is carried out by the following Example explained.

Beispiel Eine Mischung von 1500 ccm Wasser und 500 ccm konzentrierter Salzsäure wird am Rückfluß erhitzt und mit 100" g ß-Oxyäthylsemicarbazidhydrochlorid in kleinen Anteilen versetzt. Die erhaltene Lösung wird 30 Minuten am Rückfluß erhitzt, dann auf Raumtemperatur abgekühlt und dann aufgearbeitet. Man erhält das 3-Aminooxazolidon-(2) in einer Ausbeute von 210/, der Theorie vom Schmelzpunkt 55 bis 62° C. Nach dem Umkristallisieren aus Äthanol steigt der Schmelzpunkt auf 69 bis 710 C.EXAMPLE A mixture of 1500 cc of water and 500 cc of concentrated hydrochloric acid is refluxed and 100 g of β-oxyethylsemicarbazide hydrochloride are added in small portions. The resulting solution is refluxed for 30 minutes, then cooled to room temperature and then worked up 3-Aminooxazolidon- (2) in a yield of 21% , the theory from melting point 55 to 62 ° C. After recrystallization from ethanol, the melting point rises to 69 to 710 C.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung von 3-Amino-oxazolidonen-(2) der allgemeinen Formel in welcher R, R1, R2 und R3 Wasserstoff, niedere Alkyl- oder Oxyalkylreste bedeuten und gleich oder verschieden sein können, dadurch gekennzeichnet, daß man ß-Oxyalkylsemicarbazide der allgemeinen Formel in welcher R, R1, R2 und R; die oben angegebene Bedeutung haben, durch Behandlung mit Säuren cyclisiert. PATENT CLAIM: Process for the preparation of 3-Amino-oxazolidonen- (2) of the general formula in which R, R1, R2 and R3 denote hydrogen, lower alkyl or oxyalkyl radicals and can be identical or different, characterized in that ß-oxyalkylsemicarbazides of the general formula in which R, R1, R2 and R; have the meaning given above, cyclized by treatment with acids.
DEE12151A 1952-02-28 1953-02-27 Process for the preparation of 3-amino-oxazolidonen- (2) Pending DE1020339B (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US1020339XA 1952-02-28 1952-02-28

Publications (1)

Publication Number Publication Date
DE1020339B true DE1020339B (en) 1957-12-05

Family

ID=22287760

Family Applications (1)

Application Number Title Priority Date Filing Date
DEE12151A Pending DE1020339B (en) 1952-02-28 1953-02-27 Process for the preparation of 3-amino-oxazolidonen- (2)

Country Status (1)

Country Link
DE (1) DE1020339B (en)

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