CH284072A - Process for the preparation of 3,4-dimethyl-5-phenyl-2-imino-thiazolidine. - Google Patents

Process for the preparation of 3,4-dimethyl-5-phenyl-2-imino-thiazolidine.

Info

Publication number
CH284072A
CH284072A CH284072DA CH284072A CH 284072 A CH284072 A CH 284072A CH 284072D A CH284072D A CH 284072DA CH 284072 A CH284072 A CH 284072A
Authority
CH
Switzerland
Prior art keywords
phenyl
thiazolidine
imino
dimethyl
preparation
Prior art date
Application number
Other languages
German (de)
Inventor
Ballmer-Rueedi Paul
Original Assignee
Ballmer Rueedi Paul
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 Ballmer Rueedi Paul filed Critical Ballmer Rueedi Paul
Publication of CH284072A publication Critical patent/CH284072A/en

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Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D277/00Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/08Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D277/12Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D277/18Nitrogen atoms

Description

  

  Verfahren zur Herstellung von     3,4-Dimethyl-5-phenyl-2-imino-thiazolidin.       In der Schweiz. Patentschrift     Nr.266997     ist ein Verfahren zur Herstellung von     3,4-Di-          methyl-5-phenyl-2-imino-thiazolidin    beschrie  ben, welches dadurch gekennzeichnet ist, dass  man ein     1-Phen@>1-1-halogen-2-methylamino-          propanhy        drohalogenid    mit einem Salz der       Thioeyansäure    in     CTegenwart    eines Lösungs  mittels umsetzt.  



  Es wurde nun gefunden, dass man     3,4-Di-          methyl-5-phenyl-2-imino-thiazolidin    auch da  durch herstellen kann, dass man     1-Phenyl-l-          rhodan    - 2 -     metliy        1a        minopropan-hydrorhodanid     in Gegenwart eines     Lösungsmittels,    zweck  mässig im alkalischen     -Medium,    erwärmt.

         1-Phenyl-l        -rhodan-2-methylaminopropanhydro-          rhodanid    wird erhalten durch Erwärmen von       -Phenyl-l-halogen-2-methyl-aminopropan-hy-          drohalogenid    mit einem Salz der     Thiocyan-          säure    in     saurem    Medium bei     pH    1 bis 2,5.  



  Die     Umlagerungsreaktion    kann sowohl in  Wasser unter zweckmässiger Zugabe von wenig       Alkalilauge    als auch in einem organischen  Lösungsmittel, wie Methanol,     Äthanol,        Butyl-          äther    oder Benzol, unter zweckmässiger Zugabe  eines alkalischen Mittels durchgeführt werden.  



  Das Verfahrensprodukt soll als Arzneimit  tel sowie als Zwischenprodukt bei der Her  stellung von Arzneimitteln Verwendung fin  den.    <I>Beispiel:</I>  26,6 g     1-Phenyl.-1-rhodan-2-methylamino-          propan-hydrorhodanid    werden in 150     ein-          Wasser    unter Erwärmen gelöst und mit  5     em3    konzentrierter Natronlauge versetzt,  worauf alsbald die kristalline Ausscheidung  von     Dimethylphenyliminothiazolidinhydrorho-          danid    beginnt, F. 190 bis     192 .    Ausbeute:  23,5 g = 88     @/o    d.     Th.     



  Aus der Lösung des     rhodanwasserstoffsau-          ren    Salzes in Wasser wird die Base durch  Zugabe von Alkali ausgefällt. Durch Aufneh  men des     öl.s    in Alkohol, Trocknen der Lösung  und Zugabe von alkoholischer Salzsäure wird  die Base in das     Hydrochlorid    vom F. 222 bis  224  übergeführt.



  Process for the preparation of 3,4-dimethyl-5-phenyl-2-imino-thiazolidine. In Switzerland. Patent No. 266997 describes a process for the preparation of 3,4-dimethyl-5-phenyl-2-imino-thiazolidine, which is characterized in that a 1-Phen @> 1-1-halogen-2 -methylamino-propanhy drohalide with a salt of thioeyanoic acid in the presence of a solvent.



  It has now been found that 3,4-dimethyl-5-phenyl-2-imino-thiazolidine can also be prepared by making 1-phenyl-1-rhodan - 2 - metliy 1a minopropane hydrorhodanide in the presence of a Solvent, expediently in an alkaline medium, heated.

         1-phenyl-1-rhodan-2-methylaminopropanhydrhodanide is obtained by heating -phenyl-1-halogen-2-methyl-aminopropane-hydrohalide with a salt of thiocyanoic acid in an acidic medium at pH 1 to 2, 5.



  The rearrangement reaction can be carried out either in water with the appropriate addition of a little alkali or in an organic solvent such as methanol, ethanol, butyl ether or benzene, with the appropriate addition of an alkaline agent.



  The process product is intended to be used as a drug and as an intermediate in the manufacture of drugs. <I> Example: </I> 26.6 g of 1-phenyl.-1-rhodane-2-methylamino-propane-hydrorhodanide are dissolved in 150 one-liter water with heating and mixed with 5 cubic meters of concentrated sodium hydroxide solution, whereupon the crystalline Excretion of dimethylphenyliminothiazolidine hydrorho- danide begins, F. 190 to 192. Yield: 23.5 g = 88% / o d. Th.



  The base is precipitated from the solution of the rhodanic acid salt in water by adding alkali. By taking up the oil in alcohol, drying the solution and adding alcoholic hydrochloric acid, the base is converted into the hydrochloride with a melting point of 222 to 224.

 

Claims (1)

PATENTANSPRUCH Verfahren zur Herstellung von 3,4-Dime- th5-1-5-phenyl-2-imino-thiazolidin, dadurch ge kennzeichnet, dass man 1-Phenyl-l-rhadan-2- methylaminopropan-hydrorhpdanid in Gegen wart eines Lösungsmittels erwärmt. UNTERANSPRUCH: Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man die Erwärmung in alkalischem Milieu durchführt. PATENT CLAIM Process for the production of 3,4-dimeth5-1-5-phenyl-2-imino-thiazolidine, characterized in that 1-phenyl-l-rhadane-2-methylaminopropane-hydrorhpdanid is heated in the presence of a solvent . SUBSTANTIAL CLAIM: Method according to claim, characterized in that the heating is carried out in an alkaline medium.
CH284072D 1950-02-09 1950-02-09 Process for the preparation of 3,4-dimethyl-5-phenyl-2-imino-thiazolidine. CH284072A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH284072T 1950-02-09

Publications (1)

Publication Number Publication Date
CH284072A true CH284072A (en) 1952-07-15

Family

ID=4484369

Family Applications (1)

Application Number Title Priority Date Filing Date
CH284072D CH284072A (en) 1950-02-09 1950-02-09 Process for the preparation of 3,4-dimethyl-5-phenyl-2-imino-thiazolidine.

Country Status (1)

Country Link
CH (1) CH284072A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE942027C (en) * 1954-08-11 1956-04-26 Knoll Ag Process for the preparation of substituted 2-iminothiazolidines

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE942027C (en) * 1954-08-11 1956-04-26 Knoll Ag Process for the preparation of substituted 2-iminothiazolidines
DE944551C (en) * 1954-08-11 1956-06-21 Knoll Ag Process for the preparation of substituted 2-iminothiazolidines

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