DE836803C - Process for the production of xanthine from uric acid - Google Patents
Process for the production of xanthine from uric acidInfo
- Publication number
- DE836803C DE836803C DEB497A DEB0000497A DE836803C DE 836803 C DE836803 C DE 836803C DE B497 A DEB497 A DE B497A DE B0000497 A DEB0000497 A DE B0000497A DE 836803 C DE836803 C DE 836803C
- Authority
- DE
- Germany
- Prior art keywords
- xanthine
- uric acid
- production
- acid
- parts
- 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
Links
- LRFVTYWOQMYALW-UHFFFAOYSA-N 9H-xanthine Chemical compound O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 title claims description 20
- LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 title claims description 13
- TVWHNULVHGKJHS-UHFFFAOYSA-N Uric acid Natural products N1C(=O)NC(=O)C2NC(=O)NC21 TVWHNULVHGKJHS-UHFFFAOYSA-N 0.000 title claims description 13
- 229940116269 uric acid Drugs 0.000 title claims description 13
- 229940075420 xanthine Drugs 0.000 title claims description 10
- 238000000034 method Methods 0.000 title claims description 8
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical class NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 8
- 238000009835 boiling Methods 0.000 claims description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- KERBAAIBDHEFDD-UHFFFAOYSA-N n-ethylformamide Chemical compound CCNC=O KERBAAIBDHEFDD-UHFFFAOYSA-N 0.000 description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- DYDNPESBYVVLBO-UHFFFAOYSA-N formanilide Chemical compound O=CNC1=CC=CC=C1 DYDNPESBYVVLBO-UHFFFAOYSA-N 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- YAPQBXQYLJRXSA-UHFFFAOYSA-N theobromine Chemical compound CN1C(=O)NC(=O)C2=C1N=CN2C YAPQBXQYLJRXSA-UHFFFAOYSA-N 0.000 description 2
- RTAPDZBZLSXHQQ-UHFFFAOYSA-N 8-methyl-3,7-dihydropurine-2,6-dione Chemical compound N1C(=O)NC(=O)C2=C1N=C(C)N2 RTAPDZBZLSXHQQ-UHFFFAOYSA-N 0.000 description 1
- 101150095408 CNMD gene Proteins 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- LPHGQDQBBGAPDZ-UHFFFAOYSA-N Isocaffeine Natural products CN1C(=O)N(C)C(=O)C2=C1N(C)C=N2 LPHGQDQBBGAPDZ-UHFFFAOYSA-N 0.000 description 1
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229960001948 caffeine Drugs 0.000 description 1
- VJEONQKOZGKCAK-UHFFFAOYSA-N caffeine Natural products CN1C(=O)N(C)C(=O)C2=C1C=CN2C VJEONQKOZGKCAK-UHFFFAOYSA-N 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- WBEPJBUBTRUGLX-UHFFFAOYSA-N formic acid;propane-1,2,3-triol Chemical compound OC=O.OCC(O)CO WBEPJBUBTRUGLX-UHFFFAOYSA-N 0.000 description 1
- 229940083251 peripheral vasodilators purine derivative Drugs 0.000 description 1
- 150000003212 purines Chemical class 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229960004559 theobromine Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/04—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Verfahren zur Herstellung von Xanthin aus Harnsäure Die Überführung von Harnsäure in Xanthin bzw. substituierte Xanbhine ist an sich lange bekannt und noch in letzter Zeit wieder bearbeitet worden. S u n d w i k (vgl. Hoppe-Seylers Zeitschrift für physiologische Chemie Bd.23, S.476 [r897], Bd.26, S. 131 [ i898/99], Bd. 76, S. 486 [1911/121) konnte I lariisäure durch Einwirkung von Glycerin-Amei sensäure bei @;ttva 200° in Xanthin überführen, allerdings nur in schlechter Ausbeute. B i 1 t z und S c h m i <L t (vgl. Liebigs Annalen der Chemie, l;<1. 43 1 . S.70 [19231) setzten Harnsäure mit Essigs<itire2inliydrid um und erhielten 8-Methylxanthin. Weiter haben B i 1 t z und B e c k (vgl. Journal für praktische Chemie [2] Bd. 118, S. 166 [1928]) das Stiirc[wiksohe Verfahren weiter ausgearbeitet und aus Harnsäure durch Behandlung mit Glycerin-:\n1eisensäure etwa 40% der Theorie Xanthin erhalten. Die Reaktionstemperatur ist 22o bis 23o°. Diese Autoren zeigten auch, daß sich an Stelle von Ameisensäure auch Formamid verwenden läßt, wobei allerdings die Ausbeute absank.Process for the production of xanthine from uric acid The conversion of uric acid into xanthine or substituted xanbhine has been known per se for a long time and has only recently been reworked. S undwik (cf. Hoppe-Seylers Zeitschrift für Physiologische Chemie Vol. 23, p. 476 [r897], Vol. 26, p. 131 [1898/99], Vol. 76, p. 486 [1911/121) could I. Convert lariic acid into xanthine by the action of glycerol-formic acid at @; ttva 200 °, but only in poor yield. B i 1 tz and S chmi <L t (cf. Liebigs Annalen der Chemie, 1; <1.43, p.70 [19231) reacted uric acid with acetic itire2inhydride and obtained 8-methylxanthine. In addition, Bitez and Beck (cf. Journal for Practical Chemistry [2], Vol. 118, p. 166 [1928]) worked out the Stiirc [wiksohe process further and made about 40 from uric acid by treatment with glycerol: \ n1icic acid % of theory received xanthine. The reaction temperature is from 22o to 23o °. These authors also showed that formamide can also be used instead of formic acid, although the yield decreased.
Es wurde nun gefunden, daß es möglich ist, die Umwandlung der Harnsäure in Xanthin so zu gestalten, daß die Ausbeuten besonders hoch sind, Erfindungsgemäß wird dieses Zieldadurch erreicht, daß man auf Harnsäure bei höherer Temperatur solche Amide der Ameisensäure einwirken läßt, die einen höheren Siedepunkt als Formamid und vorzugsweise einen über 200° gelegenen Siedepunkt aufweisen. Beispielsweise wandelt Äthylformamid bei etwas über 200° gelegener Temperatur und Formanilid bei etwa 24o° Harnsäure in fast quantitativer Ausbeute in Xanthin um.It has now been found that it is possible to convert uric acid to make in xanthine so that the yields are particularly high, according to the invention this goal is achieved by using uric acid at a higher temperature such Amides of formic acid can act, which have a higher boiling point than formamide and preferably have a boiling point above 200 °. For example converts ethylformamide at a temperature slightly above 200 ° and formanilide about 240 ° uric acid in almost quantitative yield in xanthine.
Die Verfahrensprodukte sind als Ausgangsmaterial für die Synthese von Purinderivaten, z. B. Theobromin, Coffein u. dgl., geeignet. Im soll die Durchführung des erfindungsgemäBen Verfahrerns durch zwei Ausführungsheispiele näher erläutert werden.The process products are used as starting material for the synthesis of purine derivatives, e.g. B. theobromine, caffeine and the like., Suitable. in the is intended to carry out the method according to the invention by means of two exemplary embodiments are explained in more detail.
Ausführungsbeispiele i. 5,Teile Harnsäure werden mit i5o Teilen Äthylformamid auf 2oo° erhitzt und bei dieser oder ein wenig höherer Temperatur so lange gehalten, bis die Harnsäure völlig in Lösung gegangen ist; was nach etwa 30 Minuten der Fall ist. Nachdem Erkalten wird das Reaktionsgemisch vom Äthylformamid befreit. Das erhaltene Rohxanthin (4,5 Teile) kann nach bekannten Methoden gereinigt werden.Embodiments i. 5 parts of uric acid are heated to 200 ° with 150 parts of ethylformamide and kept at this temperature or a slightly higher temperature until the uric acid has completely dissolved; which is the case after about 30 minutes. After cooling, the reaction mixture is freed from ethylformamide. The raw xanthine obtained (4.5 parts) can be purified by known methods.
2. 5 Teile Harnsäure werden mit i5o Teilen Formanilid rasch auf etwa 24o° erhitzt und bei dieser oder ein wenig höherer Temperatur so lange gehalten, bis .die Harnsäure, völlig in Lösung gegangen ist, was nach etwa 30 -bis 40 Minuten erreicht ist. Nach dem Erkalten wird das Reaktionsgemisch vom Formarnilid befreit, z. B. mit heißem Alkohol. Das erhaltene Rohxanthin (4,5 Teile) kann nach den bekannten Methoden gereinigt werden.2. 5 parts of uric acid are rapidly reduced to about 150 parts of formanilide Heated to 24o ° and kept at this temperature or a slightly higher temperature for so long until the uric acid has completely dissolved, which takes about 30 to 40 minutes is reached. After cooling, the reaction mixture is freed from the formarnilide, z. B. with hot alcohol. The raw xanthine obtained (4.5 parts) can according to the known Methods to be cleaned.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB497A DE836803C (en) | 1949-11-01 | 1949-11-01 | Process for the production of xanthine from uric acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB497A DE836803C (en) | 1949-11-01 | 1949-11-01 | Process for the production of xanthine from uric acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE836803C true DE836803C (en) | 1952-04-17 |
Family
ID=6951893
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEB497A Expired DE836803C (en) | 1949-11-01 | 1949-11-01 | Process for the production of xanthine from uric acid |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE836803C (en) |
-
1949
- 1949-11-01 DE DEB497A patent/DE836803C/en not_active Expired
Non-Patent Citations (1)
| Title |
|---|
| None * |
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