AT396932B - Process for the preparation of 5-hydroxy-2-imino-4- imidazolinone - Google Patents
Process for the preparation of 5-hydroxy-2-imino-4- imidazolinone Download PDFInfo
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- AT396932B AT396932B AT109092A AT109092A AT396932B AT 396932 B AT396932 B AT 396932B AT 109092 A AT109092 A AT 109092A AT 109092 A AT109092 A AT 109092A AT 396932 B AT396932 B AT 396932B
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- hydroxy
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- imidazolinone
- alcohol
- filtered
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/88—Nitrogen atoms, e.g. allantoin
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
AT 396 932 BAT 396 932 B
Die Erfindung betrifft ein Verfahren zur Herstellung von 5-Hydroxy-2-imino-4-imidazolinon (5-Hydroxy-glycocyamidin).The invention relates to a process for the preparation of 5-hydroxy-2-imino-4-imidazolinone (5-hydroxy-glycocyamidine).
Glycocyamidinderivate werden bereits in der europäischen PatentschriftEP-0381628beschrieben, gemäß dieser Patentschrift müssen die Verbindungen jedoch in einer vierstufigen Synthese hergestellt werden.Glycocyamidine derivatives are already described in European patent EP-0381628, but according to this patent the compounds have to be prepared in a four-step synthesis.
Eskonntenun unerwarteterweise ein Verfahren zur Herstellung von 5-Hydroxyglycocyamidin gefunden werden, das von dem gemäß EP-0 099 981 leicht zugänglichen Glyoxylsäuremethylesterhalbacetal ausgeht und die gewünschte Verbindung in nur einem einzigen Reaktionsschritt in hoher Ausbeute und Reinheit liefertIt was unexpectedly possible to find a process for the preparation of 5-hydroxyglycocyamidine which starts from the glyoxylic acid methyl ester hemiacetal which is easily accessible according to EP-0 099 981 and which provides the desired compound in a single reaction step in high yield and purity
Gegenstand der Erfindung ist demnach ein Verfahren zur Herstellung von 5-Hydroxy-2-imino4-imidazolinon der FormellThe invention accordingly relates to a process for the preparation of 5-hydroxy-2-imino4-imidazolinone of the formula
OO
H HO —H HO -
HNHN
NHNH
NH oder dessen pharmazeutisch verträglichen Salze, das dadurch gekennzeichnet ist daß Glyoxylsäuremethylesterhalb-acetal in Gegenwart eines Alkohols mit Guanidincarbonat umgesetzt wird und das dabei ausfallende Reaktionsprodukt anschließend abfiltriert wird.NH or its pharmaceutically acceptable salts, which is characterized in that glyoxylic acid methyl ester half-acetal is reacted with guanidine carbonate in the presence of an alcohol and the reaction product which precipitates is then filtered off.
Bei dem erfindungsgemäßen Verfahren wird ein Überschuß an Alkohol in einem geeigneten Reaktionsgefäß vorgelegt Als Alkohol eignen sich besonders Methanol und Ethanol, bevorzugt wird jedoch Methanol eingesetzt Es soll dabei soviel Alkohol eingesetzt werden, daß nach Zugabe der Reaktionspartner eine noch gut rührbare, etwa 20 - 30 %ige Suspension entstehtIn the process according to the invention, an excess of alcohol is placed in a suitable reaction vessel. Methanol and ethanol are particularly suitable as alcohol, but methanol is preferably used % suspension is formed
Dem Alkohol werden zuerst Glyoxylsäuremethylesterhalbacetal (GMHA) und anschließend Guanidincarbonat bei Raumtemperatur in äquivalenten Mengen zudosiert Ein geringer Überschuß an GMHA kann ebenfalls verwendet werden, es ist jedoch von Vorteil, GMHA und Guanidincarbonat in einem Verhältnis von 2:1 einzusetzen.Equivalent amounts of methyl ester hemiacetal (GMHA) and then guanidine carbonate are added to the alcohol at room temperature in equivalent amounts. A small excess of GMHA can also be used, but it is advantageous to use GMHA and guanidine carbonate in a ratio of 2: 1.
Die so erhaltene Suspension wird dann etwa 45 bis 90 Minuten, bevorzugt etwa 55 - 70 Minuten, auf Rückflußtemperatur erhitzt, wobei CO2 entweichtThe suspension obtained in this way is then heated to the reflux temperature for about 45 to 90 minutes, preferably about 55-70 minutes, CO2 being released
Anschließend läßt man das Reaktionsgemisch auf Raumtemperatur abkühlen, wobei 5-Hydroxyglycocyamidin ausfallt Der gebildete Niederschlag wird abfiltriert und mit dem Alkohol gewaschen, der auch bei der Reaktion eingesetzt wurde. Gegebenenfalls kann eine Reinigung durch übliche Methoden, wie etwa Umkristallisieien, erfolgen.The reaction mixture is then allowed to cool to room temperature, 5-hydroxyglycocyamidine precipitating out. The precipitate formed is filtered off and washed with the alcohol which was also used in the reaction. If necessary, cleaning can be carried out by customary methods, such as recrystallization.
Beispiel 1 5-Hvdroxvglvcocvamidin 100 ml Methanol wurden in einem Rundkolben vorgelegt und der Reihe nach 12 g (0,1 mol) GMHA und 9 g (0,05 mol) Guanidincarbonat bei Raumtemperatur zudosiert Anschließend wurde 60 Minuten auf Rückflußtemperatur erhitzt wobei CO2 entwich. Das Reaktionsgemisch wurde auf Raumtemperatur abkühlen gelassen, wobei sich ein Niederschlag bildete, der abfiltriert und mit Methanol gewaschen wurde. Es wurden 10,5 g (913 % d. Th.) an 5-Hydroxyglycocyamidin erhalten.Example 1 5-Hvdroxvglvcocvamidin 100 ml of methanol were placed in a round bottom flask and 12 g (0.1 mol) GMHA and 9 g (0.05 mol) guanidine carbonate were metered in at room temperature. The mixture was then heated to reflux temperature for 60 minutes, with CO2 escaping. The reaction mixture was allowed to cool to room temperature to form a precipitate which was filtered off and washed with methanol. 10.5 g (913% of theory) of 5-hydroxyglycocyamidine were obtained.
ElemgntaranalYse; berechnet gefunden c 31,3 31,2 H 4,4 4,6 N 36,5 36,1 C13-NMR: delta = 187,25 ppm (C = NH), 171,55 ppm (C = O), 79,09 ppm (HC-OH) -2-Elemental Analysis; calculated found c 31.3 31.2 H 4.4 4.6 N 36.5 36.1 C13-NMR: delta = 187.25 ppm (C = NH), 171.55 ppm (C = O), 79 , 09 ppm (HC-OH) -2-
Claims (4)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT109092A AT396932B (en) | 1992-05-26 | 1992-05-26 | Process for the preparation of 5-hydroxy-2-imino-4- imidazolinone |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT109092A AT396932B (en) | 1992-05-26 | 1992-05-26 | Process for the preparation of 5-hydroxy-2-imino-4- imidazolinone |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| ATA109092A ATA109092A (en) | 1993-05-15 |
| AT396932B true AT396932B (en) | 1993-12-27 |
Family
ID=3506373
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT109092A AT396932B (en) | 1992-05-26 | 1992-05-26 | Process for the preparation of 5-hydroxy-2-imino-4- imidazolinone |
Country Status (1)
| Country | Link |
|---|---|
| AT (1) | AT396932B (en) |
-
1992
- 1992-05-26 AT AT109092A patent/AT396932B/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| ATA109092A (en) | 1993-05-15 |
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|---|---|---|---|
| ELJ | Ceased due to non-payment of the annual fee |