CH256229A - Process for the preparation of an alkyl-substituted dicyandiamide. - Google Patents

Process for the preparation of an alkyl-substituted dicyandiamide.

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Publication number
CH256229A
CH256229A CH256229DA CH256229A CH 256229 A CH256229 A CH 256229A CH 256229D A CH256229D A CH 256229DA CH 256229 A CH256229 A CH 256229A
Authority
CH
Switzerland
Prior art keywords
ethyl
alkyl
preparation
dicyandiamide
production
Prior art date
Application number
Other languages
German (de)
Inventor
Limited Imperial Ch Industries
Original Assignee
Ici Ltd
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 Ici Ltd filed Critical Ici Ltd
Publication of CH256229A publication Critical patent/CH256229A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
    • C07C279/28—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to cyano groups, e.g. cyanoguanidines, dicyandiamides

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

Description

  

  Verfahren zur Herstellung eines     alkylsubstituierten        Dieyandiamids.       Vorliegende Erfindung bezieht sich auf  die Herstellung von     N-Äthy        ldieyandiamid,     welches eine neue Verbindung darstellt., die       .ils    Zwischenprodukt in der chemischen     Syn-          the-#e    und insbesondere bei der Herstellung  von     Biguaniddc        rivaten    wertvoll ist.  



  Das     N-Äthyldicyandiamid,    welches auch  als     N-Äthylcyangua.nidin    bezeichnet werden       Luin,        wird        erfindungsgemäss    dadurch     erha.l-          ien,    dass     N-Äthyl-N'-cyano-S-a1kyl-isothio-          barnstoff    mit     Ammonia.h    zur Umsetzung ge  bracht     -wird.     



  Der als Ausgangsmaterial verwendete     hT-          t@tliyl-N'-cy        aiio-S-alkyl-isothioharnstoff        lä,sst     sich durch Umsetzung von     Äthyl-isothiocya-          nat    mittels N     atriumcyanamid    in Alkohol und       durch    nachträgliche direkte     Alkylierung          (beispielsweise    mit     -llethyljodid)    des Reak  tionsproduktes, welches aus dem     Natriumsalz     des     N-Äthyl-N'-cy        ano-isothioharnstoffes    be  steht,

   leicht     hergestellen.     



       Das    folgende Beispiel diene zur Erläute  rung der vorliegenden Erfindung.  



       Beispiel:          14,;    Teile     N-Äthyl-N'-cyano=S-methyl-          isothioliarnstoff    und 160 Teile einer bei     Lim-          inertemperatur    gesättigten alkoholischen     Am-          moniaklösung         =erden    während 6 Stunden  zusammen auf     120     C im geschlossenen Ge  fäss erhitzt.

   Das Gemisch     wird    gekühlt, das       Gefäss    geöffnet und die     flüchtigen    Bestand-    teile durch Erhitzen auf dem Wasserbade  unter vermindertem     Druck        abdestilliert.    Es  verbleibt das     N-Äthyldicyandnamid    in Form  eines Öls, welches in Wasser löslich ist und  als Kristalle vom     Smp.    von 65 bis 66  C er  halten     wird,    sofern eine heisse     Dioxanlösung     kühlen     gelassen    wird. Die neue, Verbindung  bildet mit     Pikrinsäure    und     F'laviansäure     Salze.  



  Der als     Ausgangsmaterial        verwendete     N-     Äthyl-N'-cyano-S-methyl-isothioharnstoff     kann dadurch erhalten werden, dass     Äthyl-          isothiocyana.t    mit     Natizumcyanamid    umge  setzt wird und     hierauf    die direkte     Alkylierung          de:s    erhaltenen     Natriumderivats    mittels     Me-          thyljodid    erfolgt.

   Das Produkt kristallisiert  aus Alkohol in     weissen        Kristallen    vom     Smp.     161     bis    163<B>0</B> C.



  Process for the preparation of an alkyl-substituted dieyandiamide. The present invention relates to the production of N-ethyl ldieyandiamide, which is a new compound which is valuable as an intermediate in chemical synthesis and in particular in the production of biguanide derivatives.



  According to the invention, N-ethyl-dicyandiamide, which is also referred to as N-ethylcyangua.nidine, is obtained by reacting N-ethyl-N'-cyano-S-alkyl-isothiobar with ammonia will be brought.



  The hT-t @ tliyl-N'-cy aiio-S-alkyl-isothiourea used as starting material can be obtained by converting ethyl isothiocyanate into alcohol by means of sodium cyanamide and by subsequent direct alkylation (for example with ethyl iodide) Reaction product, which consists of the sodium salt of N-ethyl-N'-cy ano-isothiourea,

   easily made.



       The following example serves to illustrate the present invention.



       Example: 14 ,; Parts of N-ethyl-N'-cyano = S-methyl-isothiolarea and 160 parts of an alcoholic ammonia solution, which is saturated at liminal temperature, are heated together for 6 hours at 120 ° C. in a closed vessel.

   The mixture is cooled, the vessel is opened and the volatile constituents are distilled off by heating on the water bath under reduced pressure. The N-ethyl dicyandnamide remains in the form of an oil, which is soluble in water and as crystals with a melting point of 65 to 66 ° C., provided that a hot dioxane solution is allowed to cool. The new compound forms salts with picric acid and flavic acid.



  The N-ethyl-N'-cyano-S-methyl-isothiourea used as starting material can be obtained by reacting ethyl isothiocyana.t with sodium cyanamide and then directly alkylating the sodium derivative obtained by means of methyl iodide.

   The product crystallizes from alcohol in white crystals with a m.p. 161 to 163 <B> 0 </B> C.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung von N-Äthyl- dicyandiamid, dadurch gekennzeichnet, dass N - Äthyl- N'- cya.no.- S-all,yl-is othioharnstoff mit Ammoniak zur Umsetzung gebracht wird. N-Äthyldicyandiamid ist ein kristallines Produkt vom Smp. 65 bis 66 C, welches mit Pikrinsäure und Flaviansäure Salze bildet und für die Herstellung von Biguanidderiva- ten wertvoll ist. PATENT CLAIM: Process for the production of N-ethyl-dicyandiamide, characterized in that N-ethyl-N'- cya.no.-S-all, yl-isothiourea is reacted with ammonia. N-Ethyl dicyandiamide is a crystalline product with a melting point of 65 to 66 C, which forms salts with picric acid and flavic acid and is valuable for the production of biguanide derivatives.
CH256229D 1945-10-08 1946-10-07 Process for the preparation of an alkyl-substituted dicyandiamide. CH256229A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB256229X 1945-10-08

Publications (1)

Publication Number Publication Date
CH256229A true CH256229A (en) 1948-08-15

Family

ID=10230648

Family Applications (3)

Application Number Title Priority Date Filing Date
CH261809D CH261809A (en) 1945-10-08 1946-10-07 Process for the preparation of an alkyl-substituted dicyandiamide.
CH256229D CH256229A (en) 1945-10-08 1946-10-07 Process for the preparation of an alkyl-substituted dicyandiamide.
CH261810D CH261810A (en) 1945-10-08 1946-10-07 Process for the preparation of an alkyl-substituted dicyandiamide.

Family Applications Before (1)

Application Number Title Priority Date Filing Date
CH261809D CH261809A (en) 1945-10-08 1946-10-07 Process for the preparation of an alkyl-substituted dicyandiamide.

Family Applications After (1)

Application Number Title Priority Date Filing Date
CH261810D CH261810A (en) 1945-10-08 1946-10-07 Process for the preparation of an alkyl-substituted dicyandiamide.

Country Status (2)

Country Link
CH (3) CH261809A (en)
NL (1) NL63282C (en)

Also Published As

Publication number Publication date
CH261809A (en) 1949-05-31
CH261810A (en) 1949-05-31
NL63282C (en)

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