DE870417C - Process for the production of caffeine - Google Patents

Process for the production of caffeine

Info

Publication number
DE870417C
DE870417C DEB10274D DEB0010274D DE870417C DE 870417 C DE870417 C DE 870417C DE B10274 D DEB10274 D DE B10274D DE B0010274 D DEB0010274 D DE B0010274D DE 870417 C DE870417 C DE 870417C
Authority
DE
Germany
Prior art keywords
caffeine
production
xanthine
yield
solution
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
DEB10274D
Other languages
German (de)
Inventor
Hellmut Dr Bredereck
Annelise Dr Martini
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.)
Individual
Original Assignee
Individual
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 Individual filed Critical Individual
Priority to DEB10274D priority Critical patent/DE870417C/en
Application granted granted Critical
Publication of DE870417C publication Critical patent/DE870417C/en
Expired legal-status Critical Current

Links

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)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Description

Verfahren zur Herstellung von Coffein Es ist bereits bekannt, Coffeini durch Methylserung von Xanthin herzustellen, jedoch ist die Ausbeute bei dieser Reaktion unibefriedigend. So hat z. B. E. F i s c h e r (Berichte der deutschen chemischen Gesellschaft 32 [1,899], 454) Coffeiin durch Erwärmen von Xanthin mit 3 Mol Normalalkali und 3 Mol Jodmethyl erhalten. Aber die Ausbeute ist nach seinen eigenen Angaben ziemlich schlecht.Process for the production of caffeine It is already known Caffeini to be produced by the methylation of xanthine, but the yield is in this case Unsatisfactory reaction. So has z. B. E. F i s c h e r (reports of the German chemical society 32 [1,899], 454) Coffeiin by heating xanthine with 3 moles of normal alkali and 3 moles of iodomethyl obtained. But the yield is up to his own information pretty bad.

H. B. i 1 t z und A. B e c k (Journal für praktische Chemie, N. F. i i8 [1928], 2o6) führen die Alkylierung des Xanthin in sehr verdünnter Lösung und mit einem großen Überschuß an Dimethylsulfat durch. Die anfangs -stark alkalische Lösung wird dabei bis zum Sauerwerden steh@engelassen, d. h. es wird der gesamte pH-Bereich vom stark alkalischen bis zum sauren durchlaufen. Die Ausbeute an Coffein beträgt 390/0.H. B. i 1 t z and A. B e c k (Journal for Practical Chemistry, N. F. i i8 [1928], 2o6) carry out the alkylation of xanthine in very dilute solution and with a large excess of dimethyl sulfate. The initially strongly alkaline The solution is left to stand until it becomes acidic, i. H. it becomes the whole Run through pH range from strongly alkaline to acidic. The yield of caffeine is 390/0.

Es wurde nun gefunden, daß man Coffein in sehr guter Ausbeute gewinnt, wenn man Xanthin bei einem pH von etwa 8 bis io mit D@imethylsulfat methyliiert.It has now been found that caffeine can be obtained in a very good yield, if xanthine is methylated with D @ imethyl sulfate at a pH of about 8 to 10.

Man gibt zweckmäß.igerweise das D:imethylsulfat und die Natronlauge so zu"daß ein pH-Wert in der Lösung von etwa 8 bis io aufrechterhalten wird. Nach beendeter Reaktion kann man das, Coffein mit Lösungsmitteln, z. B. Chloroform, extrahieren. Die Ausbeute an. Coffein beträgt etwa 9o °/o. `@Beispiel- Zu iog Xanthin, aufgeschlämmt in Wa;sser,- werden bei pH 8 bis 9 24,ccm Dime"thylsulfat und- i8 ccm 37o/oige Natronlauge . gegeben (Tempe- ratur 35°). Die wäßrigie Lösung ward mit Chloro- form extrahiert: Nach Abdampfen des Chloroforms- hinterbleiben io bis i i g Coffein. The methyl sulfate and sodium hydroxide solution are expediently added in such a way that a pH value of about 8 to 10 is maintained in the solution. After the reaction has ended, the caffeine can be extracted with solvents, e.g. chloroform. The yield of caffeine is about 90%. `@ Example To iog xanthine, slurried in water, are at pH 8 to 9 24, ccm dimethyl sulfate and- 18 cc 37% sodium hydroxide solution. given (temperature temperature 35 °). The aqueous solution was treated with chlorine form extracted: After evaporation of the chloroform left behind io to iig caffeine.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung von Coffein durch Methylierung von, Xanthin mit Dimethylsitjfat, dadurch gekennzeichnet, daß man die Umsetzung bei einem pH von B. bis io *durchführt. Angezogene Druckschriften L a s.s a r - C o h n : »Arbeitsmethoden für organisch-chemische Laboratorien«, 5. Aufl., Spezieller Teil, S. 188; Berichte der deutschen chemischen Gesellschaft, Bd. 35, S. 322; Journal für praktische Chemie, NF. 118 [i928], S. 2o6 und 2o7.PATENT CLAIM: Process for the production of caffeine by methylation von, xanthine with Dimethylsitjfat, characterized in that the reaction at a pH of B. to io *. Referred publications L a s.s a r - C o h n: "Working methods for organic-chemical laboratories", 5th edition, special Part, p. 188; Reports of the German Chemical Society, Vol. 35, p. 322; journal for practical chemistry, NF. 118 [1928], pp. 2o6 and 2o7.
DEB10274D 1943-03-02 1943-03-02 Process for the production of caffeine Expired DE870417C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEB10274D DE870417C (en) 1943-03-02 1943-03-02 Process for the production of caffeine

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEB10274D DE870417C (en) 1943-03-02 1943-03-02 Process for the production of caffeine

Publications (1)

Publication Number Publication Date
DE870417C true DE870417C (en) 1953-03-12

Family

ID=6956735

Family Applications (1)

Application Number Title Priority Date Filing Date
DEB10274D Expired DE870417C (en) 1943-03-02 1943-03-02 Process for the production of caffeine

Country Status (1)

Country Link
DE (1) DE870417C (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE944312C (en) * 1953-08-09 1956-06-14 Boehringer Sohn Ingelheim Process for the N-alkylation of compounds which are free of reactive methylene groups and contain NH groups in heterocyclic grouping which are connected to a CO group directly or through a system of conjugated double bonds

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
None *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE944312C (en) * 1953-08-09 1956-06-14 Boehringer Sohn Ingelheim Process for the N-alkylation of compounds which are free of reactive methylene groups and contain NH groups in heterocyclic grouping which are connected to a CO group directly or through a system of conjugated double bonds

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