CH228147A - Process for the preparation of 5-5-C-C-1-cycloheptenyl-methyl-N-methyl-barbituric acid. - Google Patents

Process for the preparation of 5-5-C-C-1-cycloheptenyl-methyl-N-methyl-barbituric acid.

Info

Publication number
CH228147A
CH228147A CH228147DA CH228147A CH 228147 A CH228147 A CH 228147A CH 228147D A CH228147D A CH 228147DA CH 228147 A CH228147 A CH 228147A
Authority
CH
Switzerland
Prior art keywords
methyl
cycloheptenyl
barbituric acid
preparation
dicyandiamide
Prior art date
Application number
Other languages
German (de)
Inventor
Ag J R Geigy
Original Assignee
Ag J R Geigy
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 Ag J R Geigy filed Critical Ag J R Geigy
Publication of CH228147A publication Critical patent/CH228147A/en

Links

Landscapes

  • Medicinal Preparation (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Description

  

  Verfahren zur Darstellung von     5-5-C-C-41-Cycloheptenyl-methyl-N-methyl-barbitursäure.       Gegenstand des vorliegenden Zusatz  patentes ist ein Verfahren zur Herstellung  von     5-5-C-C-d1-Cycloheptenyl-methyl-N-me-          thyl-barbitursäure,    dadurch gekennzeichnet,  dass ein     dl-Cycloheptenyl-methyl-cyanessig-          säureester    mit     Dicyandiamid    kondensiert,

   das  erhaltene Produkt mit     Dimethylsulfat        me-          thyliert    und das als Zwischenprodukt ent  stehende     Cyan-iminoderivat    zur     Barbitur-          säureverbindung        hydrolysiert    wird.  



  <I>Beispiel:</I>  20,7 Teile     dl-Cycloheptenyl-methyl-cyan-          essigsäuremethylester    erhitzt man mit einer  Lösung von 4,6 Teilen Natrium in 100 Tei  len Methanol unter Zugabe von 9 Teilen       Dicy        andiamid    8 Stunden auf ca. 70 . Nach  dem Erkalten fügt man tropfenweise 24 Teile       Dimethylsulfat    hinzu, wobei     man    dafür  Sorge trägt, dass die Temperatur nicht über  50  steigt.  



  Hierauf verjagt man das Methanol im    Wasserbade und verkocht den Rückstand mit  der zehnfachen Menge<B>25%</B> Schwefelsäure.  Die sich abscheidende     C-C-Cycloheptenyl-          methyl-N-methyl-barbitursäure    bildet nach  dem     Umlösen    aus<B>30%</B> Alkohol farblose  Prismen vom F. 124 .



  Process for the preparation of 5-5-C-C-41-cycloheptenyl-methyl-N-methyl-barbituric acid. The subject of the present additional patent is a process for the production of 5-5-C-C-d1-cycloheptenyl-methyl-N-methyl-barbituric acid, characterized in that a dl-cycloheptenyl-methyl-cyanoacetic acid ester condenses with dicyandiamide,

   the product obtained is methylated with dimethyl sulfate and the cyano-imino derivative formed as an intermediate is hydrolyzed to the barbituric acid compound.



  <I> Example: </I> 20.7 parts of dl-cycloheptenyl-methyl-cyano-acetic acid methyl ester are heated with a solution of 4.6 parts of sodium in 100 parts of methanol with the addition of 9 parts of dicyandiamide for 8 hours for approx. 70. After cooling, 24 parts of dimethyl sulfate are added dropwise, taking care that the temperature does not rise above 50.



  The methanol is then chased away in a water bath and the residue is boiled with ten times the amount <B> 25% </B> sulfuric acid. The C-C-cycloheptenyl-methyl-N-methyl-barbituric acid which separates out forms colorless prisms of F. 124 after dissolving from <B> 30% </B> alcohol.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung von 5-5-C-C dl-Cycloheptenyl-methyl-N-methyl-barbitur- säure, dadurch gekennzeichnet, dass ein dl Cycloheptenyl-methyl-cyanessigsäureestermit Dicyandiamid kondensiert, das erhaltene Pro dukt mit Dimethylsulfat methyliert und das als Zwischenprodukt entstehende Cyan-imino- derivat zur Barbitursäureverbindung hydro- lysiert wird. PATENT CLAIM: Process for the production of 5-5-CC dl-cycloheptenyl-methyl-N-methyl-barbituric acid, characterized in that a dl cycloheptenyl-methyl-cyanoacetic acid ester condenses with dicyandiamide, the product obtained is methylated with dimethyl sulfate and that as an intermediate resulting cyano-imino derivative is hydrolyzed to the barbituric acid compound. Die neue Verbindung wird nach dem Umlösen aus Alkohol in Form farbloser Nadeln von schwach bitterem Geschmack, Schmelzpunkt 124 , erhalten. Sie besitzt wertvolle therapeutische Eigenschaften. The new compound is obtained after dissolving from alcohol in the form of colorless needles with a slightly bitter taste, melting point 124. It has valuable therapeutic properties.
CH228147D 1940-03-09 1941-03-07 Process for the preparation of 5-5-C-C-1-cycloheptenyl-methyl-N-methyl-barbituric acid. CH228147A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
CH228147X 1940-03-09
CH228147T 1941-03-07
CH224789T 1941-03-07

Publications (1)

Publication Number Publication Date
CH228147A true CH228147A (en) 1943-07-31

Family

ID=27177946

Family Applications (1)

Application Number Title Priority Date Filing Date
CH228147D CH228147A (en) 1940-03-09 1941-03-07 Process for the preparation of 5-5-C-C-1-cycloheptenyl-methyl-N-methyl-barbituric acid.

Country Status (1)

Country Link
CH (1) CH228147A (en)

Similar Documents

Publication Publication Date Title
CH228147A (en) Process for the preparation of 5-5-C-C-1-cycloheptenyl-methyl-N-methyl-barbituric acid.
CH224899A (en) Process for the preparation of 4-oxy-1-dimethylaminoacetoxy-2-methyl-naphthalene-chloromethylate.
CH85310A (en) Process for the preparation of allyl morphine.
DE823446C (en) Process for the production of thiosemicarbazones
CH235225A (en) Process for the preparation of 5.7-dibromo-8-oxy-quinaldine.
DE526719C (en) Process for the preparation of diacetyldiphenolisatin
CH261821A (en) Process for the preparation of a substituted 2,4-diamino-1,3,5-triazine.
CH187362A (en) Process for the production of symm. Cyanuric acid di (2-methyl-4-aminoquinolyl-6) diamide.
CH228146A (en) Process for the preparation of 5-5-C-C- 1-Cycloheptenylethylbarbituric acid.
CH221819A (en) Process for the preparation of 2-methyl-4-aminopyrimidine-5-carboxylic acid ethyl ester.
CH203592A (en) Process for the preparation of an aminoarylsulfone.
CH176225A (en) Process for the preparation of 2-chloro-2&#39;-aminoazobenzene.
CH188765A (en) Process for the preparation of a quinoline series amino compound.
CH171981A (en) Process for the preparation of a barbituric acid derivative.
CH272249A (en) Process for the preparation of a derivative of benzotetronic acid.
CH169509A (en) Process for the preparation of a derivative of 5,5-phenylethylhydantoin.
CH93749A (en) Process for the preparation of a halogen-substituted barbituric acid derivative.
CH179692A (en) Process for the preparation of 1-methyl-5,5-phenylmethylhydantoin.
CH221220A (en) Process for the preparation of 3,5-dimethyl-isoxazole-carboxylic acid- (4) -di-n-propyl-amide.
CH191417A (en) Process for the preparation of 4&#39;-oxyphenyl-2-aminochrysen.
CH276621A (en) Process for the preparation of p-amino-salicylic acid-n-butylmide.
CH179691A (en) Process for the preparation of 1,3-dimethyl-5,5-phenylmethylhydantoin.
CH211294A (en) Process for the production of a condensation product.
CH135161A (en) Process for the preparation of isobutylallylbarbituric acid.
CH307482A (en) Process for the preparation of N.S-diacetylcysteamine.