DE842060C - Process for the production of synthetic caffeine - Google Patents

Process for the production of synthetic caffeine

Info

Publication number
DE842060C
DE842060C DEB1643D DEB0001643D DE842060C DE 842060 C DE842060 C DE 842060C DE B1643 D DEB1643 D DE B1643D DE B0001643 D DEB0001643 D DE B0001643D DE 842060 C DE842060 C DE 842060C
Authority
DE
Germany
Prior art keywords
caffeine
alkali
production
diamino
dioxypyrimidine
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
Application number
DEB1643D
Other languages
German (de)
Inventor
Bruno Dr Walach
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.)
CH Boehringer Sohn AG and Co KG
Original Assignee
CH Boehringer Sohn AG and Co KG
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 CH Boehringer Sohn AG and Co KG filed Critical CH Boehringer Sohn AG and Co KG
Priority to DEB1643D priority Critical patent/DE842060C/en
Application granted granted Critical
Publication of DE842060C publication Critical patent/DE842060C/en
Expired legal-status Critical Current

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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
    • C07D473/06—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3
    • C07D473/12—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3 with methyl radicals in positions 1, 3, and 7, e.g. caffeine

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Description

Verfahren zur Herstellung von synthetischem Coffein Die vorliegende Erfindung betrifft ein Verfahren zur Herstellung von synthetischem Coffein durch Methylierung von Monoformyl-4, 5-diamino-2, 6-dioxypyrimidin mit Chlormethyl.Process for the manufacture of synthetic caffeine The present Invention relates to a method for the production of synthetic caffeine by Methylation of monoformyl-4,5-diamino-2,6-dioxypyrimidine with chloromethyl.

Bei der Herstellung von Monoformyl- t, 3-dimethyl-4, 5-diamino-2, 6-dioxypyrimidin durch Behandlung von Monoformyl-4, 5-diamino-2, 6-dioxypyrimidin oderl Moiroformyl-.3-methyl-4,, 5-diamino-2, 6-dioxypyrimidirr mit Methylierungsmitteln bei niedrigen Temperaturen entsteht als Nebenprodukt Coffein, wenn man mit Alkalimengen arbeitet, die in bezug auf die für die Herstellung von Monoformyl- r, 3-dimethyl-4, 5-diamino-2, 6-dioxypyrimidin erforderliche theoretische Menge einen Überschußdarstellen. Bei Verwendung von Monoformyl-4, 5-diamino-2, 6-dioxypyrimidin als Ausgangsmaterial sind 2 Mol Alkali und bei Verwendung von MonofOtmyl-3-methyl-4, 5-diamino-2, 6-dioxypyrimidin r Mol Alkali nach der Theorie erforderlich.In the production of monoformyl- t, 3-dimethyl-4, 5-diamino-2, 6-dioxypyrimidine by treating monoformyl-4, 5-diamino-2, 6-dioxypyrimidine oderl Moiroformyl-3-methyl-4, 5-diamino-2,6-dioxypyrimidir with methylating agents At low temperatures, caffeine is produced as a by-product when dealing with amounts of alkali works in relation to the production of monoformyl-r, 3-dimethyl-4, 5-diamino-2,6-dioxypyrimidine required theoretical amount represent an excess. When using monoformyl-4, 5-diamino-2, 6-dioxypyrimidine as starting material are 2 moles of alkali and when using MonofOtmyl-3-methyl-4, 5-diamino-2, 6-dioxypyrimidine r mole of alkali required according to the theory.

Bei derlHersbellungvon Coffeinaus;MonoforrnyT-4, 5-diamino-2, 6-dioxypyrimiditt durch Behandlung mit Methylierungsmitteln werden theoretisch 3 Mol Alkali benötigt. Bei Verwendung dieser Menge ist indessen. wie festgestellt wurde, keine optimale Ausbeute an Coffein zu erzielen.In the production of caffeine from; MonoforrnyT-4, 5-diamino-2, 6-dioxypyrimidite treatment with methylating agents theoretically requires 3 moles of alkali. However, when using this amount. as found, not an optimal one Achieve yield of caffeine.

Erfindungsgemäß wird daher in der Weise gearbeitet, daß erheblich mehr als 3 Mol Alldali; verwendet werden. Bei Anwendung eines derartigen Alkaliüberschusses werden beim Arbeiten mit überschüssigem Chlormethyl Ausbeuten von über 9o% der Theorie an Coffein erhalten. Dabei ist es zweckmäßig, bei Temperaturen von 7o bis 95° zu arbeiten.According to the invention is therefore worked in such a way that significantly more than 3 moles of alldali; be used. When using such an excess of alkali when working with excess chloromethyl yields of over 90% the Theory of caffeine received. It is useful at temperatures from 7o to 95 ° to work.

In Anbetracht der hohen Empfindlichkeit von Coffein gegen Alkali bei höheren Temperaturen (vgl. Berichte der Deutschen Chemischen Gesellschaft, Bd.31, .S.3269 und Bd.61. S. 1409) war der Erfolg eines Arbeitens bei höheren Temperaturen mit erheblichem Alkaliüberschuß nicht ohne weiteres vorauszusehen, da eine Schädigung des Coffeins zu erwarten war.In view of the high sensitivity of caffeine to alkali higher temperatures (see reports of the German Chemical Society, Vol. 31, .P.3269 and vol.61. P. 1409) was the success of working at higher temperatures with a considerable excess of alkali cannot be foreseen without further ado, since damage will result of caffeine was to be expected.

Vorzugsweise wird bei der Durchführung des erfindungsmäßigen Verfahrens mit Alkalimengen von 3,6 bis 4 Mol pro Mol angewandtes Monoformyl-4, 5-diamino-2, 6-dioxypyrimidin gearbeitet.When carrying out the method according to the invention, preference is given to with alkali amounts of 3.6 to 4 moles per mole of monoformyl-4, 5-diamino-2 used, 6-dioxypyrimidine worked.

Im folgenden soll die Durchführung des erfindungsmäßigen Verfahrens an Hand eines Ausführungsbeispieles näher erläutert werden: Beispiel 7,65 kg rohes Monoformyl-4, 5-diamino-2, 6-dioxypyrimidin (45 MOI) werden mit 281 Wasser in einem Rührwerksautoklaven von 651 Inhalt zusammen mit i o kg Chlormethyl (198 Mol) erwärmt und bei einer Temperatur von 81 bis 8 5° im Verlauf von 3 bis 31i Stunden 14,9k9 45 oioige Na.trönlärxge (167,6 Mol), d. h. 3,73 Mol Alkali je Mol Formylverbindung, eingedrückt. Nachdem diese Alkalimenge -eingeführt -ist, wird der Autoklaveninhalt über ein Entspannungsgefäß bei gleichzeitiger Wiedergewinnung des Chlormethylüberschusses entleert. Es werden 8, t kg Coffein (Molgewicht 194) vom F. 232 bis 233° erhalten. Die Ausbeute beträgt 92,8% der Theorie.In the following, the implementation of the method according to the invention will be explained in more detail using an exemplary embodiment: Example 7.65 kg of crude monoformyl-4,5-diamino-2,6-dioxypyrimidine (45 MOI) are combined with 281 of water in a stirrer autoclave with a capacity of 651 io heated with chloromethyl kg (198 mol), and at a temperature of 81-8 5 ° over a period of 3 to 31i hours 14,9k9 45 oioige Na.trönlärxge (167.6 mol), ie 3.73 moles of alkali per mole of formyl compound , depressed. After this amount of alkali has been introduced, the contents of the autoclave are emptied via an expansion vessel while the excess chloromethyl is recovered at the same time. 8. t kg of caffeine (molecular weight 194) with a temperature of 232 to 233 ° are obtained. The yield is 92.8% of theory.

Verwendet nran bei dem gleichen Ansatz 12,o kg 45 %ige Natronlauge (135 Mol), d. h. 3,o Mol je Mol Formylverbindung, so werden nur 4,4 kg Coffein, d. h. 50,40;o der Theorie erhalten.In the same batch, 12.0 kg of 45% sodium hydroxide solution are used (135 moles), i.e. H. 3, o moles per mole of formyl compound, only 4.4 kg of caffeine, d. H. 50.40; o obtained from theory.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung von Coffein durch Methylierung von Monoformyl-4, 5-diamino-2, 6-dioxypyrimidin, dadurch gekennzeichnet, daß die Methylierung mit überschüssigem Chlormethyl bei Temperaturen von etwa 7o bis 95° und bei Gegenwart eines Alkaliüberschusses, d. h. mit mehr als 3 Mol Alkali, vorgenommen wird. Angezogene Druckschriften: Deutsche Patentschrift Nr. 148 2o8.PATENT CLAIM: Process for the production of caffeine by methylation of monoformyl-4, 5-diamino-2, 6-dioxypyrimidine, characterized in that the Methylation with excess chloromethyl at temperatures of about 7o to 95 ° and in the presence of an excess of alkali, d. H. with more than 3 moles of alkali will. Referenced publications: German patent specification No. 148 2o8.
DEB1643D 1942-03-05 1942-03-05 Process for the production of synthetic caffeine Expired DE842060C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEB1643D DE842060C (en) 1942-03-05 1942-03-05 Process for the production of synthetic caffeine

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEB1643D DE842060C (en) 1942-03-05 1942-03-05 Process for the production of synthetic caffeine

Publications (1)

Publication Number Publication Date
DE842060C true DE842060C (en) 1952-06-23

Family

ID=6952379

Family Applications (1)

Application Number Title Priority Date Filing Date
DEB1643D Expired DE842060C (en) 1942-03-05 1942-03-05 Process for the production of synthetic caffeine

Country Status (1)

Country Link
DE (1) DE842060C (en)

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