CH242292A - Process for the preparation of a quaternary salt of the dimethylcarbamic acid ester of o-dimethylaminophenol. - Google Patents

Process for the preparation of a quaternary salt of the dimethylcarbamic acid ester of o-dimethylaminophenol.

Info

Publication number
CH242292A
CH242292A CH242292DA CH242292A CH 242292 A CH242292 A CH 242292A CH 242292D A CH242292D A CH 242292DA CH 242292 A CH242292 A CH 242292A
Authority
CH
Switzerland
Prior art keywords
acid ester
dimethylcarbamic acid
dimethylaminophenol
quaternary salt
preparation
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 CH242292A publication Critical patent/CH242292A/en

Links

Landscapes

  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Description

  

  Verfahren zur Herstellung eines     quaternären    Salzes des     Dimethylcarbaminsäureesters     des     o-Dimethylamino-phenols.       Die     quaternären    Salze des     Dimethylcarb-          aminsäureesters    des     m-Dimethylamino-phe-          nols    haben sich als therapeutisch wertvolle       Verbindungen        erwiesen.     



  Es wurde nun     gefunden,    dass bei den     qua-          ternären    Salzen des     Dimethylcarbaminsäure-          esters    des     o-Dimethylamino-phenols    die glei  chen     therapeutischen    Eigenschaften noch viel       günstiger    ausgeprägt sind.

   So zeigt zum  Beispiel der     Dimethylcarbaminsäureester     des     o-Ogyphenyl-trimethylammonium    -     bro-          mids    im Vergleich mit den bis jetzt haupt  sächlich therapeutisch verwerteten     quater-          nären    Salzen des     Dimethylcarbaminsäure-          esters    des     m-Dimethylaminö-phenols    bei voll  ständig erhaltener     Aktivität    nur . halbe       Toxizität.     



  Die     quaternären    Salze des     Dimethylcarb-          aminsäureesters    des     o-Dimethylamino-phenols     bilden farblose     Kristalle,    die     in    Wasser sehr  leicht mit neutraler Reaktion, in Alkohol    leicht und in Äther schwer löslich sind. Sie  sollen als Arzneimittel verwendet werden.  



  Gegenstand des vorliegenden Patentes ist  ein Verfahren zur     Herstellung    eines     quater-          nären    Salzes des     Dimethylcarbaminsäure-          esters    des     o-Dimethylamino-phenols,    bei wel  chem der     Dimethylcarbaminsäureester    des     o-          Dimethylamino-phenols    durch     Einwirkung     von     Dimethylsulfat        in    das     quaternäre    Salz  übergeführt wird.

     <I>Beispiel:</I>  208 Gewichtsteile     Dimethylcarbamin-          säureester    des     o-Dimethylamino-phenols    wer  den     in    trockenem Aceton     mit    126 Gewichts  teilen     Dimethylsulfat    versetzt. Nach einiger  Zeit beginnt die     Kristallisation,    die nach  etwa 48     Stunden    beendet ist. Der von der  Flüssigkeit abgetrennte     Dimethylcarbamin-          säureester    des     o-Oxyphenyl-trimethylammo-          nium-methylsulfats        schmilzt    bei 148 .

   Er löst  sich leicht in Wasser     und    Alkohol     und        ist          unlöslich    in Äther und Benzol.



  Process for the preparation of a quaternary salt of the dimethylcarbamic acid ester of o-dimethylaminophenol. The quaternary salts of the dimethylcarbamic acid ester of m-dimethylaminophenol have proven to be therapeutically valuable compounds.



  It has now been found that with the quaternary salts of the dimethylcarbamic acid ester of o-dimethylaminophenol, the same therapeutic properties are even more favorable.

   Thus, for example, the dimethylcarbamic acid ester of o-ogyphenyl-trimethylammonium bromide, in comparison with the quaternary salts of the dimethylcarbamic acid ester of m-dimethylamino-phenol, which has so far mainly been used therapeutically, only shows fully retained activity. half toxicity.



  The quaternary salts of the dimethylcarbamic acid ester of o-dimethylaminophenol form colorless crystals which are very easily soluble in water with a neutral reaction, easily soluble in alcohol and sparingly in ether. They are intended to be used as medicines.



  The subject of the present patent is a process for the production of a quaternary salt of the dimethylcarbamic acid ester of o-dimethylaminophenol, in wel chem the dimethylcarbamic acid ester of o-dimethylaminophenol is converted into the quaternary salt by the action of dimethyl sulfate.

     <I> Example: </I> 208 parts by weight of dimethylcarbamic acid ester of o-dimethylaminophenol are mixed with 126 parts by weight of dimethyl sulfate in dry acetone. After some time, the crystallization begins, which ends after about 48 hours. The dimethylcarbamic acid ester of o-oxyphenyltrimethylammonium methyl sulfate separated from the liquid melts at 148.

   It dissolves easily in water and alcohol and is insoluble in ether and benzene.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines quater- nären Salzes des Dimethylcarbaminsäure- esters des o-Dimethylamino-phenols, dadurch gekennzeichnet, PATENT CLAIM: Process for the production of a quaternary salt of the dimethylcarbamic acid ester of o-dimethylaminophenol, characterized in that dass der Dimethylcarbamin- säureester des o - Dimethylamino - Phenols durch Einwirkung von Dimethylsulfat in das quaternäre Salz übergeführt wird. Der bisher unbekannte Dimethylcarbamin- säureester des o-Ogyphenyl-trimethylammo- nium-methylsulfat ist eine kristalline Ver bindung, welche sich leicht in Wasser und Alkohol, that the dimethylcarbamic acid ester of o-dimethylamino-phenol is converted into the quaternary salt by the action of dimethyl sulfate. The previously unknown dimethylcarbamic acid ester of o-ogyphenyl-trimethylammonium-methylsulfate is a crystalline compound, which can easily be dissolved in water and alcohol, nicht dagegen in Äther und Benzol löst. Sein Schmelzpunkt liegt bei 148 . does not, however, dissolve in ether and benzene. Its melting point is 148.
CH242292D 1944-06-15 1944-06-15 Process for the preparation of a quaternary salt of the dimethylcarbamic acid ester of o-dimethylaminophenol. CH242292A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH242292T 1944-06-15
CH239300T 1944-06-15

Publications (1)

Publication Number Publication Date
CH242292A true CH242292A (en) 1946-04-30

Family

ID=25728397

Family Applications (1)

Application Number Title Priority Date Filing Date
CH242292D CH242292A (en) 1944-06-15 1944-06-15 Process for the preparation of a quaternary salt of the dimethylcarbamic acid ester of o-dimethylaminophenol.

Country Status (1)

Country Link
CH (1) CH242292A (en)

Similar Documents

Publication Publication Date Title
CH242292A (en) Process for the preparation of a quaternary salt of the dimethylcarbamic acid ester of o-dimethylaminophenol.
CH239300A (en) Process for the preparation of a quaternary salt of the dimethylcarbamic acid ester of o-dimethylaminophenol.
DE963514C (en) Process for the production of poorly soluble, crystallized streptomycin and dihydrostreptomycin salts
AT235823B (en) Process for the preparation of form hydrazoic esters
DE440772C (en) Process for the preparation of acridine cyanide
AT144906B (en) Process for the preparation of compounds from C.C-disubstituted barbituric acids and pyrazolone derivatives.
CH263037A (en) Process for the preparation of a new derivative of 2-oxy-5-aminobenzoic acid.
CH243026A (en) Process for the preparation of a soluble salt of 4,4&#39;-di-amidino-diphenyl ether.
CH208133A (en) Process for the production of a new, nitrogen-containing organic compound.
CH240070A (en) Process for the preparation of a derivative of a carboxylic acid.
CH208131A (en) Process for the production of a new, nitrogen-containing organic compound.
CH218521A (en) Process for the preparation of a diphenyl sulfone derivative.
CH197718A (en) Process for the preparation of an aminobenzenesulfonic acid amide derivative.
CH284278A (en) Process for the preparation of a compound of phenyl-ethyl-barbituric acid.
CH246555A (en) Process for the production of a bile acid derivative.
CH207203A (en) Process for the production of a new, nitrogen-containing organic compound.
CH235763A (en) Process for the preparation of a thiophanone derivative.
CH303833A (en) Process for the preparation of derivatives of tetrahydro-γ-carboline.
CH299530A (en) Process for the preparation of 4- (B-amino-γ-bromo-propyl) -imidazole-dihydrobromide.
CH291379A (en) Process for the preparation of a new thioether.
CH199680A (en) Process for the preparation of 2,4-dioxo-3,3-di-n-propyl-5-bromo-6-methyl-tetrahydropyridine.
CH307798A (en) Process for the preparation of a salt of 4-amino-salicylic acid.
CH224899A (en) Process for the preparation of 4-oxy-1-dimethylaminoacetoxy-2-methyl-naphthalene-chloromethylate.
CH285622A (en) Process for the preparation of a diuretically active substituted 2,4-diamino-1,3,5-triazine.
CH208129A (en) Process for the production of a new, nitrogen-containing organic compound.