DE1020339B - Process for the preparation of 3-amino-oxazolidonen- (2) - Google Patents
Process for the preparation of 3-amino-oxazolidonen- (2)Info
- 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
Links
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 229940127089 cytotoxic agent Drugs 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- 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)
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) |
-
1953
- 1953-02-27 DE DEE12151A patent/DE1020339B/en active Pending
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