CH281035A - Process for the preparation of p-methylureido-benzalthiosemicarbazone. - Google Patents

Process for the preparation of p-methylureido-benzalthiosemicarbazone.

Info

Publication number
CH281035A
CH281035A CH281035DA CH281035A CH 281035 A CH281035 A CH 281035A CH 281035D A CH281035D A CH 281035DA CH 281035 A CH281035 A CH 281035A
Authority
CH
Switzerland
Prior art keywords
benzalthiosemicarbazone
preparation
methylureido
allowed
methyl
Prior art date
Application number
Other languages
German (de)
Inventor
Ag Dr A Wander
Original Assignee
Ag Dr A Wander
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 Dr A Wander filed Critical Ag Dr A Wander
Publication of CH281035A publication Critical patent/CH281035A/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

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

Description

  

  Verfahren zur Herstellung von     p-Methylureido-benzalthiosemicarbazon.       Es ist bereits im Hauptpatent angegeben  worden, dass die     p-Alky1ureido-benzalthiosemi-          carbazone    eine hemmende Wirkung auf das  Wachstum von Tuberkelbazillen ausüben.    Gegenstand der vorliegenden Erfindung  ist, ein Verfahren zur Herstellung von     p-Me-          thylureido-benzalthiosemicarbazon    der Formel  
EMI0001.0006     
    welches dadurch gekennzeichnet ist, dass man  den     Methylester    der     Isoeyansäure    auf p  Amino-benzaltlriosemiearbazon einwirken lässt.  Die Umsetzung wird vorzugsweise in einem  Lösungsmittel, wie z.

   B.     Py        ridin,    Aceton,     Di-          oxan,    vorgenommen.  



       Beispiel:     32     Gewichtsteile    p     Amirro-benzalthiosemi-          carbazon    werden in 150     (Tewichtsteilen        Pyri-          din    gelöst und mit 7.5 Gewichtsteilen     Methyl-          isoeyanat    versetzt. Die Lösung erwärmt sich  spontan langsam auf etwa 35 . Sie wird nach  einer Stunde Stehen noch eine Stunde auf       dein        Dampfbad    erwärmt und sodann in ver  dünnte Salzsäure eingerührt. Dabei scheidet  sieh ein gelbliches, bald erstarrendes Harz ab.

    Dieses wird     abgesauet    und mit Wasser nach-    gewaschen. Zur Reinigung wird es nun in  etwa 1 Liter 5      /oiger    Natronlauge bei 30 bis       40     aufgenommen, die trübe Lösung mit Tier  kohle versetzt und abgesaugt. Aus dem Filtrat.  wird das Produkt durch Ansäuern als gelb  liches Pulver ausgefällt und nun in der ge  rade nötigen Menge kochendem Alkohol ge  löst und heiss mit dem doppelten Volumen hei  ssen Wassers vermischt und erkalten gelassen.  



  Dabei scheidet sich das gebildete     p-Methvl-          ureido-benzalthiosemiearbazon    in feinen gelb  lichen Kristallen vom F. 220      (Zers.)    aus. Es  soll als Heilmittel verwendet. werden.



  Process for the preparation of p-methylureido-benzalthiosemicarbazone. It has already been stated in the main patent that the p-alky1ureido-benzalthiosemicarbazones exert an inhibiting effect on the growth of tubercle bacilli. The present invention provides a process for the preparation of p-methylureido-benzalthiosemicarbazone of the formula
EMI0001.0006
    which is characterized in that the methyl ester of isoeyanic acid is allowed to act on p-amino-benzaltlriosemiearbazon. The reaction is preferably carried out in a solvent such as.

   B. pyridine, acetone, dioxane made.



       Example: 32 parts by weight of amirro-benzalthiosemicarbazone are dissolved in 150 parts by weight of pyridine and 7.5 parts by weight of methyl isoeyanate are added. The solution slowly warms up spontaneously to about 35. After standing for an hour, it will be on the steam bath for another hour warmed up and then stirred into dilute hydrochloric acid, whereupon a yellowish, soon solidifying resin separates.

    This is drained and washed with water. For cleaning, it is now taken up in about 1 liter of 5% sodium hydroxide solution at 30 to 40, the cloudy solution is mixed with animal charcoal and suctioned off. From the filtrate. the product is precipitated as a yellowish powder by acidification and then dissolved in the right amount of boiling alcohol, mixed hot with twice the volume of hot water and allowed to cool.



  The p-methylo-ureido-benzalthiosemiearbazon formed is precipitated in fine yellowish crystals with a melting point of 220 (decomp.). It is said to be used as a remedy. will.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung von p-Methyl- ureido-benzalthiosemicarbazon der Formel EMI0001.0032 dadureb gekennzeichnet, dass man den Methyl- ester der Isocyansäure auf p-Amino-benzal- thiosemiearbazon einwirken lässt. Das erhaltene Produkt bildet feine gelb liche Kristalle vom F. 232 (Zers. j. PATENT CLAIM: Process for the preparation of p-methyl ureido-benzalthiosemicarbazone of the formula EMI0001.0032 dadureb indicates that the methyl ester of isocyanic acid is allowed to act on p-amino-benzal-thiosemiearbazon. The product obtained forms fine yellowish crystals of F. 232 (decomp. J.
CH281035D 1949-12-21 1949-12-21 Process for the preparation of p-methylureido-benzalthiosemicarbazone. CH281035A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH281035T 1949-12-21
CH278134T 1949-12-21

Publications (1)

Publication Number Publication Date
CH281035A true CH281035A (en) 1952-02-15

Family

ID=25731805

Family Applications (1)

Application Number Title Priority Date Filing Date
CH281035D CH281035A (en) 1949-12-21 1949-12-21 Process for the preparation of p-methylureido-benzalthiosemicarbazone.

Country Status (1)

Country Link
CH (1) CH281035A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8765802B2 (en) 2007-06-12 2014-07-01 Provid Pharmaceuticals, Inc. Kinase inhibitors, compositions thereof, and methods of use therewith

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8765802B2 (en) 2007-06-12 2014-07-01 Provid Pharmaceuticals, Inc. Kinase inhibitors, compositions thereof, and methods of use therewith

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