DE2641979A1 - PROCESS FOR THE PREPARATION OF 5-AMINOCARBONYL-2,4,6-TRIHYDROXYPYRIMIDINE - Google Patents
PROCESS FOR THE PREPARATION OF 5-AMINOCARBONYL-2,4,6-TRIHYDROXYPYRIMIDINEInfo
- Publication number
- DE2641979A1 DE2641979A1 DE19762641979 DE2641979A DE2641979A1 DE 2641979 A1 DE2641979 A1 DE 2641979A1 DE 19762641979 DE19762641979 DE 19762641979 DE 2641979 A DE2641979 A DE 2641979A DE 2641979 A1 DE2641979 A1 DE 2641979A1
- Authority
- DE
- Germany
- Prior art keywords
- urea
- aminocarbonyl
- trihydroxypyrimidine
- preparation
- acid
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/60—Three or more oxygen or sulfur atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Paper (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pyridine Compounds (AREA)
Description
Die Erfindung bezieht sich auf ein neues Verfahren zur Herstellung von 5-Aminocarbonyl-2,4,6-trihydroxypyrimidin, welches sich unter anderem als Zwischenprodukt für die Herstellung von Farbstoffen eignet.The invention relates to a new process for the preparation of 5-aminocarbonyl-2,4,6-trihydroxypyrimidine, which is suitable, inter alia, as an intermediate for the preparation of dyes.
Es ist bekannt, 5-Aminocarbonyl-2,4,6-trihydroxypyrimidin dadurch herzustellen, dass man Harnstoff und Barbitursäure gemeinsam in Gegenwart von Kaliumcyanat erhitzt oder dass man Harnstoff und Barbitursäure gemeinsam in stark polaren Lösungsmitteln, wie z.B. 1-Methyl-2-pyrrolidon, erhitzt.It is known that 5-aminocarbonyl-2,4,6-trihydroxypyrimidine can be prepared by heating urea and barbituric acid together in the presence of potassium cyanate or by heating urea and barbituric acid together in strongly polar solvents such as 1-methyl-2-pyrrolidone , heated.
Gemäß der Erfindung wird nunmehr ein neues Verfahren zur Herstellung von 5-Aminocarbonyl-2,4,6-trihydroxypyrimidin vorgeschlagen, welches dadurch ausgeführt wird, dass man Barbitursäure mit einer wässrigen Lösung von Harnstoff erhitzt.According to the invention, a new process for the preparation of 5-aminocarbonyl-2,4,6-trihydroxypyrimidine is now proposed, which is carried out by heating barbituric acid with an aqueous solution of urea.
Es wird bevorzugt, einen stöchimetrischen Überschuss an Harnstoff, und zwar insbesondere 3 bis 8 Mol Harnstoff je Mol Barbitursäure, zu verwenden. Größere Mengen können verwendet werden, ergeben aber offensichtlich keinen ausreichenden Vorteil, als dass die übermäßigen Kosten aufgewogen würden.It is preferred to use a stoichimetric excess of urea, in particular 3 to 8 moles of urea per mole of barbituric acid. Larger amounts can be used but obviously do not provide sufficient benefit to outweigh the excessive cost.
Das Gewicht der verwendeten Wassermenge ist vorzugsweise mindestens gleich dem Gewicht des verwendeten Harnstoffs. Unter normalen Umständen ist es mindestens zweimal so groß wie das Gewicht des Harnstoffs, da sonst die Zersetzung des Produkts im Reaktionsgemisch während des Verlaufs der Reaktion zu Schwierigkeiten beim Rühren führt. Gewünschtenfalls kann anstelle von Wasser alleine als Verdünnungsmittel ein Gemisch aus Wasser mit einer kleineren Menge einer mit Wasser mischbaren organischen Flüssigkeit, wie z.B. Äthylenglycol, verwendet werden. Es kann auch ein oberflächenaktives Mittel dem Reaktionsgemisch zugesetzt werden.The weight of the amount of water used is preferably at least equal to the weight of the urea used. Under normal circumstances it will be at least twice the weight of the urea, otherwise the decomposition of the product in the reaction mixture during the course of the reaction will lead to difficulties in stirring. If desired, a mixture of water with a minor amount of a water-miscible organic liquid such as ethylene glycol can be used as the diluent instead of water alone. A surfactant can also be added to the reaction mixture.
Das gebildete Produkt ist vermutlich ein Ammoniumsalz von 5-Aminocarbonylbarbitursäure. Die freie Säure kann durch Zusatz von wässriger Säure, beispielsweise wässriger Salzsäure, erhalten werden.The product formed is believed to be an ammonium salt of 5-aminocarbonylbarbituric acid. The free acid can be obtained by adding aqueous acid, for example aqueous hydrochloric acid.
Das neue Verfahren ergibt eine Anzahl von betriebstechnischen Vorteilen gegenüber den bekannten Verfahren. Beispielsweise wird die Verwendung eines großen Überschusses an Harnstoff und die Rückgewinnung von teuren Lösungsmitteln vermieden.The new method results in a number of operational advantages over the known methods. For example, will the use of a large excess of urea and the recovery of expensive solvents are avoided.
Die Erfindung wird nun durch die folgenden Beispiele näher erläutert, worin die Teile und Prozentangaben in Gewicht ausgedrückt sind.The invention will now be explained in more detail by the following examples, in which the parts and percentages are expressed by weight.
Beispiel 1example 1
128 Teile Barbitursäure werden zu einer Lösung von 240 Teilen Harnstoff und 8,5 Teilen des Natriumsalzes eines Kondensats von Formaldeyd und Naphthalinsulfonsäure in 600 Teilen Wasser zugegeben. Das Gemisch wird 18 st auf Rückfluß erhitzt und dann auf 50°C abgekühlt, durch Zusatz von 200 Teilen 34,5%iger wässriger Salzsäure angesäuert, 16 st gerührt und dann auf Raumtemperatur abkühlen gelassen. Das Produkt wird abfiltriert, mit kaltem Wasser von Säure freigewaschen und bei 100°C getrocknet. Es werden 131 g 5-Aminocarbonyl-2,4,6-trihydroxyprimidin erhalten.128 parts of barbituric acid are added to a solution of 240 parts of urea and 8.5 parts of the sodium salt of a condensate of formaldehyde and naphthalenesulfonic acid in 600 parts of water. The mixture is heated to reflux for 18 hours and then cooled to 50 ° C., acidified by adding 200 parts of 34.5% strength aqueous hydrochloric acid, stirred for 16 hours and then allowed to cool to room temperature. The product is filtered off, washed free of acid with cold water and dried at 100.degree. 131 g of 5-aminocarbonyl-2,4,6-trihydroxyprimidine are obtained.
Einzelheiten und Ausbeuten weiterer Beispiele finden sich in der folgenden Tabelle. Das Verfahren war das gleiche wie in Beispiel 1, wobei jedoch Änderungen hinsichtlich des Harnstoffs, des Lösungsmittels und des oberflächenaktiven Mittels durchgeführt wurden.Details and yields of further examples can be found in the following table. The procedure was the same as in Example 1 except that changes were made to the urea, solvent and surfactant.
Claims (5)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB4575575A GB1499850A (en) | 1975-11-04 | 1975-11-04 | Process for the manufacture of 5-aminocarbonyl-2,4,6-trihydroxypyrimidine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2641979A1 true DE2641979A1 (en) | 1977-05-12 |
Family
ID=10438457
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19762641979 Pending DE2641979A1 (en) | 1975-11-04 | 1976-09-17 | PROCESS FOR THE PREPARATION OF 5-AMINOCARBONYL-2,4,6-TRIHYDROXYPYRIMIDINE |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS5259176A (en) |
| CH (1) | CH599170A5 (en) |
| DE (1) | DE2641979A1 (en) |
| FR (1) | FR2330683A1 (en) |
| GB (1) | GB1499850A (en) |
| IT (1) | IT1070801B (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0191474A1 (en) * | 1985-02-15 | 1986-08-20 | Ciba-Geigy Ag | Barbituric-acid derivatives |
| EP0192180A1 (en) * | 1985-02-15 | 1986-08-27 | Ciba-Geigy Ag | 5-(Azolyloxyphenylcarbamoyl)-barbituric acid derivatives as active agents in anthelmics |
-
1975
- 1975-11-04 GB GB4575575A patent/GB1499850A/en not_active Expired
-
1976
- 1976-09-13 IT IT2715676A patent/IT1070801B/en active
- 1976-09-17 DE DE19762641979 patent/DE2641979A1/en active Pending
- 1976-10-12 FR FR7630645A patent/FR2330683A1/en active Granted
- 1976-11-01 JP JP13158076A patent/JPS5259176A/en active Pending
- 1976-11-01 CH CH1374676A patent/CH599170A5/xx not_active IP Right Cessation
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0191474A1 (en) * | 1985-02-15 | 1986-08-20 | Ciba-Geigy Ag | Barbituric-acid derivatives |
| EP0192180A1 (en) * | 1985-02-15 | 1986-08-27 | Ciba-Geigy Ag | 5-(Azolyloxyphenylcarbamoyl)-barbituric acid derivatives as active agents in anthelmics |
| US4762830A (en) * | 1985-02-15 | 1988-08-09 | Ciba-Geigy Corporation | 5-(azolyloxyphenylcarbamoyl)barbituric acid derivatives as anthelmintics |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2330683B3 (en) | 1979-06-22 |
| GB1499850A (en) | 1978-02-01 |
| JPS5259176A (en) | 1977-05-16 |
| IT1070801B (en) | 1985-04-02 |
| FR2330683A1 (en) | 1977-06-03 |
| CH599170A5 (en) | 1978-05-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHJ | Non-payment of the annual fee |