CH220970A - Process for the preparation of a condensation product. - Google Patents

Process for the preparation of a condensation product.

Info

Publication number
CH220970A
CH220970A CH220970DA CH220970A CH 220970 A CH220970 A CH 220970A CH 220970D A CH220970D A CH 220970DA CH 220970 A CH220970 A CH 220970A
Authority
CH
Switzerland
Prior art keywords
condensation product
preparation
monomethylurea
nitrobenzenesulfonamide
reduction
Prior art date
Application number
Other languages
German (de)
Inventor
A-G J R Geigy
Original Assignee
Geigy Ag J R
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 Geigy Ag J R filed Critical Geigy Ag J R
Publication of CH220970A publication Critical patent/CH220970A/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/50—Compounds containing any of the groups, X being a hetero atom, Y being any atom
    • C07C311/52—Y being a hetero atom
    • C07C311/54—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea

Description

  

  Verfahren zur Darstellung eines Kondensationsproduktes.    Gegenstand des vorliegenden Zusatzpaten  tes ist ein Verfahren zur Darstellung eines  Kondensationsproduktes, welches dadurch ge  kennzeichnet ist, dass ein Salz des     p-Nitro-          benzolsulfonamids    mit     Methylisocyansäure-          ester    kondensiert und der entstandene     N-(p-          Nitrobenzolsulfon)    - N'-     monomethylharnstoff     durch     Reduktion    in das entsprechende     Amino-          derivat    übergeführt wird.

   Die neue Verbin  dung ist ein farbloses Kristallpulver vom  F.<B>173'</B> und besitzt     wertvolle    therapeutische  Eigenschaften.  



  <I>Beispiel:</I>  135 Teile trockenes, feinverteiltes     p-nitro-          benzolsulfonamidsaures    Natrium werden     in     300     Volumteilen        Nitrobenzol    suspendiert und  unter Rühren mit 20 Teilen     Methylisocyan-          säureester    versetzt. Das Reaktionsgemisch  wird 15 Stunden auf 50 bis 60   gehalten,  dann mit Wasser versetzt, mit Essigsäure       phenolphthaleinneutral,    jedoch     lackmusalka-          lisch    gestellt und filtriert.

   Die     wässrige    Lö  sung wird abgetrennt,     ausgeäthert    und an  gesäuert. Das gefällte Kondensationsprodukt  wird mit Wasser gewaschen und aus Alkohol  umkristallisiert, F. 213  .    Durch Reduktion mit Wasserstoff und  Nickelkatalysator wird der     N-(p-Aminoben-          zolsulfon)-N'-monomethylharnstoff    folgender  Konstitution  
EMI0001.0026     
    erhalten, F.173  .  



  Mit gleichem Erfolg lässt sich die Reak  tion auch mit andern Salzen, beispielsweise  dem Kalium- oder     Calciumsalz    des     p-Nitro-          benzolsulfonamids,    ausführen.



  Process for the preparation of a condensation product. The subject of the present additional patent is a process for the preparation of a condensation product, which is characterized in that a salt of p-nitrobenzenesulfonamide condenses with methyl isocyanate and the resulting N- (p-nitrobenzenesulfone) -N'-monomethylurea by reduction is converted into the corresponding amino derivative.

   The new compound is a colorless crystal powder from F. <B> 173 '</B> and has valuable therapeutic properties.



  <I> Example: </I> 135 parts of dry, finely divided sodium p-nitrobenzenesulfonamides are suspended in 300 parts by volume of nitrobenzene, and 20 parts of methyl isocyanate are added while stirring. The reaction mixture is kept at 50 to 60 hours for 15 hours, then water is added, phenolphthalein-neutral with acetic acid, but litmus alkaline, and filtered.

   The aqueous solution is separated off, extracted with ether and acidified. The precipitated condensation product is washed with water and recrystallized from alcohol, mp 213. By reduction with hydrogen and a nickel catalyst, the N- (p-aminobenzenesulfone) -N'-monomethylurea is given the following constitution
EMI0001.0026
    received, F.173.



  The reaction can also be carried out with other salts, for example the potassium or calcium salt of p-nitrobenzenesulfonamide, with the same success.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung eines Konden- sationsproduktes, dadurch gekennzeichnet, dass ein Salz des p-Nitrobenzolsulfonamids mit Methylisocyansäureester kondensiert und der entstandene N-(p-Nitrobenzolsulfon)-N'- monomethylharnstoff durch Reduktion in das entsprechende Aminoderivat übergeführt wird. Die neue Verbindung ist ein farbloses Kristallpulver vom F. 173 und besitzt wert volle therapeutische Eigenschaften. Claim: Process for the preparation of a condensation product, characterized in that a salt of p-nitrobenzenesulfonamide condenses with methyl isocyanate and the resulting N- (p-nitrobenzenesulfone) -N'-monomethylurea is converted into the corresponding amino derivative by reduction. The new compound is a colorless crystal powder from F. 173 and has valuable therapeutic properties.
CH220970D 1939-12-23 1939-12-23 Process for the preparation of a condensation product. CH220970A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH215241T 1939-12-23
CH220970T 1939-12-23

Publications (1)

Publication Number Publication Date
CH220970A true CH220970A (en) 1942-04-30

Family

ID=25725705

Family Applications (1)

Application Number Title Priority Date Filing Date
CH220970D CH220970A (en) 1939-12-23 1939-12-23 Process for the preparation of a condensation product.

Country Status (1)

Country Link
CH (1) CH220970A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2977375A (en) * 1953-02-11 1961-03-28 Boehringer & Soehne Gmbh Process of manufacturing n-sulphanilyl ureas
DE1127345B (en) * 1953-02-11 1962-04-12 Boehringer & Soehne Gmbh Process for the preparation of N-sulfanilyl-N- (n-butyl) urea

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2977375A (en) * 1953-02-11 1961-03-28 Boehringer & Soehne Gmbh Process of manufacturing n-sulphanilyl ureas
DE1127345B (en) * 1953-02-11 1962-04-12 Boehringer & Soehne Gmbh Process for the preparation of N-sulfanilyl-N- (n-butyl) urea

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