CH132529A - Process for the preparation of allyl isobutyl acetylurea. - Google Patents

Process for the preparation of allyl isobutyl acetylurea.

Info

Publication number
CH132529A
CH132529A CH132529DA CH132529A CH 132529 A CH132529 A CH 132529A CH 132529D A CH132529D A CH 132529DA CH 132529 A CH132529 A CH 132529A
Authority
CH
Switzerland
Prior art keywords
allyl
preparation
acetylurea
alcohol
isobutylacetylurea
Prior art date
Application number
Other languages
German (de)
Inventor
F Hoffmann- Aktiengesellschaft
Original Assignee
Hoffmann La Roche
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 Hoffmann La Roche filed Critical Hoffmann La Roche
Publication of CH132529A publication Critical patent/CH132529A/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C273/00—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C273/18—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas
    • C07C273/1854—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas by reactions not involving the formation of the N-C(O)-N- moiety

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

  

  Verfahren zur Darstellung von     Allylisobutylazetylharnstoff.       Unter den Ureiden der     disubstituierten     Essigsäure finden sich Verbindungen von  sehr guter hypnotischer Wirkung. Für die  Gewinnung solcher Verbindungen stand bis  her hauptsächlich der Weg über den     Malon-          ester,    den     Monoalkylmalonester,    den     Dialkyl-          malonester,    die     Dialkylmalonsäure    offen..  Dabei war eine zeitraubende Isolierung von       Zwischenprodukten    notwendig.  



  Gegenstand der vorliegenden Erfindung  ist ein Verfahren.     gemäss    welchem man mit  guter Ausbeute zum     Allylisobutylacetyl-          harnstoff    gelangen kann. Es ist dadurch  gekennzeichnet, dass man     Allylisobutylbar-          bitursäure    in schwach alkalischer Lösung  erhitzt. Da sämtliche Reaktionen in alka  lischer Lösung verlaufen, so ist die Isolie  rung der Zwischenprodukte nicht erforder  lich.  



  Der     Allylisobutylacetylharnstoff    kristal  lisiert aus Alkohol in farblosen Nadeln vom  Schmelzpunkt 139  . Er löst sich in Alkohol  und Chloroform leicht, in Äther ziemlich    schwer. In Wasser ist er fast unlöslich. Die  Verbindung soll als Arzneimittel Verwen  dung finden.  



  <I>Beispiel:</I>  22,4 Teile     Allylisobutylbarbitursäure     werden in 250 Teilen 2,5     %igem    wässerigem  Ammoniak gelöst und 48 Stunden auf dem  siedenden Wasserbad     erhitzt.    Während dem  Erhitzen beginnt der     Allylisobutylacetyl-          harnstoff    bereits auszufallen. Beim Abküh  len nimmt der Niederschlag zu. Er     wird    von  der Flüssigkeit getrennt, mit verdünntem  Ammoniak nachgewaschen. Durch     Umkri-          stallisieren    aus Alkohol erhält man den  reinen     Allylisobutylacetylharnstoff    vom  Schmelzpunkt 139  .



  Process for the preparation of allyl isobutyl acetylurea. Among the ureides of disubstituted acetic acid are compounds with a very good hypnotic effect. To obtain such compounds, the main route up to now was via the malonic ester, the monoalkyl malonic ester, the dialkyl malonic ester and the dialkyl malonic acid. This required the time-consuming isolation of intermediates.



  The present invention relates to a method. according to which one can get to allylisobutylacetyl urea with good yield. It is characterized in that allyl isobutylbarbituric acid is heated in a weakly alkaline solution. Since all reactions take place in alkaline solution, isolation of the intermediate products is not required.



  The allyl isobutylacetylurea crystallizes from alcohol in colorless needles with a melting point of 139. It dissolves easily in alcohol and chloroform, rather heavily in ether. It is almost insoluble in water. The compound is intended to be used as a medicinal product.



  <I> Example: </I> 22.4 parts of allylisobutylbarbituric acid are dissolved in 250 parts of 2.5% aqueous ammonia and heated on a boiling water bath for 48 hours. The allyl isobutylacetyl urea begins to precipitate during the heating process. When cooling down, the precipitation increases. It is separated from the liquid and washed with dilute ammonia. The pure allylisobutylacetylurea with a melting point of 139 is obtained by recrystallization from alcohol.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung von Allyl- isobutylacetylharnstoff, dadurch gekenn zeichnet, daB man Allylisobutylbarbitur- säure in schwach alkalischer Lösung er hitzt. Der Allylisobutylacetylharnstoff kristal- lisiert aus Alkohol in farblosen Nadeln vom Schmelzpunkt 139 . Er löst sich in Alkohol und Chloroform leicht, in Äther ziemlich schwer. In Wasser ist er fast unlöslich. Die Verbindung soll als Arzneimittel Verwen dung finden. PATENT CLAIM: Process for the preparation of allyl isobutylacetylurea, characterized in that allyl isobutylbarbituric acid is heated in a weakly alkaline solution. The allyl isobutylacetylurea crystallizes from alcohol in colorless needles with a melting point of 139. It dissolves easily in alcohol and chloroform, rather heavily in ether. It is almost insoluble in water. The compound is intended to be used as a medicinal product.
CH132529D 1928-11-10 1928-11-10 Process for the preparation of allyl isobutyl acetylurea. CH132529A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH132529T 1928-11-10
CH119327T 1930-09-26

Publications (1)

Publication Number Publication Date
CH132529A true CH132529A (en) 1929-04-15

Family

ID=25709245

Family Applications (1)

Application Number Title Priority Date Filing Date
CH132529D CH132529A (en) 1928-11-10 1928-11-10 Process for the preparation of allyl isobutyl acetylurea.

Country Status (1)

Country Link
CH (1) CH132529A (en)

Similar Documents

Publication Publication Date Title
CH132529A (en) Process for the preparation of allyl isobutyl acetylurea.
DE812316C (en) Process for the preparation of 2- (p-aminobenzenesulfonamido) -4-methylpyrimidine
CH151588A (en) Process for the preparation of allyl sec.-butylazetylurea.
DE372842C (en) Process for the preparation of amidines
CH119642A (en) Process for the preparation of diallylazetylurea.
AT158301B (en) Process for the production of vitamin B1.
DE713079C (en) Process for the preparation of clusters of 4-aminobenzenesulfonamides
DE921148C (en) Process for the preparation of a condensation product from a p-aminobenzenesulfonamidopyrimidine, cinnamaldehyde and alkali bisulfite
DE730018C (en) Process for the preparation of imidazolines containing sulfuric acid residues
CH119327A (en) Process for the preparation of allylisopropylacetylurea.
DE415314C (en) Process for the production of a nuclear brominated acetobrenzcatechin dibenzyl ether
CH143616A (en) Process for the preparation of a guanidine derivative.
DE903574C (en) Process for the preparation of Pentaerythritdiiodohydrinphosphoric acid
CH116815A (en) Process for the preparation of the phenyl ester of 4-nitro-1-aminobenzene-2-sulfonic acid.
DE537767C (en) Production of acridyl-9-carbamic acid esters
DE575364C (en) Process for the production of water-soluble organic salts, in particular soaps
DE581328C (en) Process for the preparation of acridone and substituted acridones
DE476663C (en) Process for the preparation of N-methylsulfurous acid salts of secondary aromatic-aliphatic amines
CH198137A (en) Process for the preparation of p-sulfamidophenylcarbamic acid choline chloride.
CH134220A (en) Process for the production of choline monoborate from choline and boric acid.
CH125397A (en) Process for the preparation of di-O-isopropylphenolisatin.
CH234990A (en) Process for the preparation of a new therapeutically effective amidine.
CH171981A (en) Process for the preparation of a barbituric acid derivative.
CH205526A (en) Process for the preparation of a 2,4-dioxo-3,3-dialkyl-tetrahydropyridine-6-carboxylic acid ester.
CH307877A (en) Process for the production of guanidyl acetic acid.