CH416595A - Process for the production of pentafluorophenyl urea or -thiourea - Google Patents

Process for the production of pentafluorophenyl urea or -thiourea

Info

Publication number
CH416595A
CH416595A CH542061A CH542061A CH416595A CH 416595 A CH416595 A CH 416595A CH 542061 A CH542061 A CH 542061A CH 542061 A CH542061 A CH 542061A CH 416595 A CH416595 A CH 416595A
Authority
CH
Switzerland
Prior art keywords
pentafluorophenyl
cyanate
urea
thiourea
production
Prior art date
Application number
CH542061A
Other languages
German (de)
Inventor
Jerzy Belf Leon
Original Assignee
Nat Smelting Company Limited
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 Nat Smelting Company Limited filed Critical Nat Smelting Company Limited
Publication of CH416595A publication Critical patent/CH416595A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C275/30—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by halogen atoms, or by nitro or nitroso groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C273/00—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C273/18—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas
    • C07C273/1809—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas with formation of the N-C(O)-N moiety
    • C07C273/1818—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas with formation of the N-C(O)-N moiety from -N=C=O and XNR'R"
    • C07C273/1827—X being H
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C275/46—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups containing any of the groups, X being a hetero atom, Y being any atom, e.g. acylureas
    • C07C275/48—Y being a hydrogen or a carbon atom
    • C07C275/50—Y being a hydrogen or an acyclic carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C275/46—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups containing any of the groups, X being a hetero atom, Y being any atom, e.g. acylureas
    • C07C275/48—Y being a hydrogen or a carbon atom
    • C07C275/54—Y being a carbon atom of a six-membered aromatic ring, e.g. benzoylureas
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C335/04—Derivatives of thiourea
    • C07C335/16—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Description

  

  



  Verfahren zur Herstellung von Pentafluor-phenyl-harnstoff   bzw.-thioharnstoff   
Die vorliegende Erfindung betrifft ein Verfahren zur Herstellung von   Pentafluor-phenyl-harnstoff    bzw.



     Pentafluor-phenyl-thioharns, toff,    das dadurch gekennzeichnet ist, dass man 2,3,4,5,6-Pentafluoranilin in saurer Lösung mit einer   Cyanat-oder    Thio  cyanat-Ionen    abgebenden Verbindung reagieren   lässt    und   dan-n    erhitzt. Die zu diesem Zwecke   benützte    Säure ist   passenderweise      Essig-oder      Chlorwasser-      stoffsäure    und als   Cyanrat-oder Thiocyanat-Ionen    abgebende Verbindungen kommen leicht lösliche Salze, z. B.   Kalium-oder    Ammoniumcyanat bzw.



  -thiocyanat in Betracht.



   Die   erfindungsgemäss    hergestellten Harnstoffe   besitzen sedative oder    hypnotische Eigenschaften.



   Beispiel   1   
Die   Herstellung von Pentafluor-phenyl-harnstoff    kann durch die folgende Reaktionsgleichung veranschaulicht wer, den :
EMI1.1     

Das Amin wurde in Eisessigsäure gelöst und zu dem Gemisch eine wässrige Lösung von Kaliumcya  nat hinzugesetzt. Das    Gemisch wurde heftig, unter Aufrechterhalten der Temperatur im Bereiche von   50-60 C    während 2   SXtunden geriihrt.    Durch   Abküh-    len fiel das Produkt aus. Anschliessend wurde dasselbe aus Athanol/Wasser rekristallisiert ; F = 161 bis   162  C.   



   Der   Pentafluor-phenyl-harnstoff ist ein    weisses, leicht wasserlösliches Material, welches am Licht blau wirkt. Es   wirld durch    starke Säuren und Alkalien nach Erwärmen zersetzt.



   Beispiel 2
Der   Pentafluor-phenyl-thioharnstoff    wurde durch Reaktion von   Pentafluor-anilin-hydrochloridsalz mit      Ammoniumthiocyamat,    in konzentrierter   Chlorwas-    serstoffsäure-Lösung, entsprechend der Gleichung :
EMI1.2     
 hergestellt.



   Zunächst   wurde das Chlorwasserstoffsalz von      Pentafluor-anilin, durch. Auflöslen    von   Pentafluor-ani-    lin in konzentrierter Chlorwasserstoffsäure bei etwa   80  C erzeugt.    Nach Abkühlen auf Zimmertemperatur wurde zu dieser Lösung   gemahlenes'Ammonium-    thiocyanat hinzugesetzt und das ganze Reaktionsgemisch auf   100  C während    3 Stunden erhitzt.



   Der Gehalt der Flasche wurde : dann bis zur Trockne abge, dampft und in Wasser bei   70  C gelöst.   



  Das Produkt schied sich nach Kühlen in feinem kri  stallinen    Plättchen aus, welche nach Rekristallisiere. n einen F = 151 bis   152 C    aufwiesen.



   Der   Pe, nbafluor-phenyl-thioharnstoff    kristallisiert in matten gelben Plättchen, und ist in Wasser sehr leicht löslich.



   Es hat sich ergeben, dass beide Verbindungen Eigenschaften für eine Verwendung als Sedativa oder Hypnotika zeigen. Sie können auch Zwischenprodukt bei der Herstellung von   tandem,    heilkräftigen Verbindungen sein.  



   PATENTANSPRUCH
Verfahren zur Herstellung von   Pentafluor-phe-      nyl-harnstoff bzw.-thioharnstoff,    dadurch gekennzeichnet, dass man 2,3,4,5,6-Pentafluor-, anilin mit 

**WARNUNG** Ende DESC Feld konnte Anfang CLMS uberlappen**.





  



  Process for the production of pentafluorophenyl urea or thiourea
The present invention relates to a process for the production of pentafluorophenyl urea or



     Pentafluorophenyl-thiourine, which is characterized in that 2,3,4,5,6-pentafluoroaniline is allowed to react in acidic solution with a compound which gives off cyanate or thio cyanate ions and then heated. The acid used for this purpose is suitably acetic or hydrochloric acid and compounds which release cyanate or thiocyanate ions are readily soluble salts, e.g. B. potassium or ammonium cyanate or



  thiocyanate into consideration.



   The ureas produced according to the invention have sedative or hypnotic properties.



   Example 1
The production of pentafluorophenyl urea can be illustrated by the following reaction equation:
EMI1.1

The amine was dissolved in glacial acetic acid and an aqueous solution of potassium cyanate was added to the mixture. The mixture was stirred vigorously, maintaining the temperature in the range of 50-60 ° C. for two and a half hours. The product precipitated out on cooling. The same was then recrystallized from ethanol / water; F = 161 to 162 C.



   Pentafluorophenyl urea is a white, easily water-soluble material that appears blue in light. It is decomposed by strong acids and alkalis after heating.



   Example 2
The pentafluorophenyl thiourea was obtained by reacting pentafluoro aniline hydrochloride salt with ammonium thiocyamate in a concentrated hydrochloric acid solution according to the equation:
EMI1.2
 manufactured.



   First, the hydrogen chloride salt of pentafluoro aniline was made by. Dissolving pentafluoro-aniline in concentrated hydrochloric acid at about 80 ° C produces. After cooling to room temperature, ground ammonium thiocyanate was added to this solution and the entire reaction mixture was heated to 100 ° C. for 3 hours.



   The contents of the bottle were: then evaporated to dryness, evaporated and dissolved in water at 70.degree.



  After cooling, the product separated out in fine, crystalline platelets, which after recrystallization. n had an F = 151 to 152 C.



   The Pe, nbafluor-phenyl-thiourea crystallizes in matt yellow flakes and is very easily soluble in water.



   Both compounds have been found to exhibit properties for use as sedatives or hypnotics. They can also be an intermediate in the making of tandem, medicinal compounds.



   PATENT CLAIM
Process for the preparation of pentafluorophenyl urea or thiourea, characterized in that 2,3,4,5,6-pentafluoro-, aniline with

** WARNING ** End of DESC field could overlap beginning of CLMS **.

Claims (1)

**WARNUNG** Anfang CLMS Feld konnte Ende DESC uberlappen **. ** WARNING ** Beginning of CLMS field could overlap end of DESC **. Verfahren zur Herstellung von Pentafluor-phenyl-harnstoff bzw.-thioharnstoff Die vorliegende Erfindung betrifft ein Verfahren zur Herstellung von Pentafluor-phenyl-harnstoff bzw. Process for the production of pentafluorophenyl urea or thiourea The present invention relates to a process for the production of pentafluorophenyl urea or Pentafluor-phenyl-thioharns, toff, das dadurch gekennzeichnet ist, dass man 2,3,4,5,6-Pentafluoranilin in saurer Lösung mit einer Cyanat-oder Thio cyanat-Ionen abgebenden Verbindung reagieren lässt und dan-n erhitzt. Die zu diesem Zwecke benützte Säure ist passenderweise Essig-oder Chlorwasser- stoffsäure und als Cyanrat-oder Thiocyanat-Ionen abgebende Verbindungen kommen leicht lösliche Salze, z. B. Kalium-oder Ammoniumcyanat bzw. Pentafluorophenyl-thiourine, which is characterized in that 2,3,4,5,6-pentafluoroaniline is allowed to react in acidic solution with a compound which gives off cyanate or thio cyanate ions and then heated. The acid used for this purpose is suitably acetic or hydrochloric acid and compounds which release cyanate or thiocyanate ions are readily soluble salts, e.g. B. potassium or ammonium cyanate or -thiocyanat in Betracht. thiocyanate into consideration. Die erfindungsgemäss hergestellten Harnstoffe besitzen sedative oder hypnotische Eigenschaften. The ureas produced according to the invention have sedative or hypnotic properties. Beispiel 1 Die Herstellung von Pentafluor-phenyl-harnstoff kann durch die folgende Reaktionsgleichung veranschaulicht wer, den : EMI1.1 Das Amin wurde in Eisessigsäure gelöst und zu dem Gemisch eine wässrige Lösung von Kaliumcya nat hinzugesetzt. Das Gemisch wurde heftig, unter Aufrechterhalten der Temperatur im Bereiche von 50-60 C während 2 SXtunden geriihrt. Durch Abküh- len fiel das Produkt aus. Anschliessend wurde dasselbe aus Athanol/Wasser rekristallisiert ; F = 161 bis 162 C. Example 1 The production of pentafluorophenyl urea can be illustrated by the following reaction equation: EMI1.1 The amine was dissolved in glacial acetic acid and an aqueous solution of potassium cyanate was added to the mixture. The mixture was stirred vigorously, maintaining the temperature in the range of 50-60 ° C. for two and a half hours. The product precipitated out on cooling. The same was then recrystallized from ethanol / water; F = 161 to 162 C. Der Pentafluor-phenyl-harnstoff ist ein weisses, leicht wasserlösliches Material, welches am Licht blau wirkt. Es wirld durch starke Säuren und Alkalien nach Erwärmen zersetzt. Pentafluorophenyl urea is a white, easily water-soluble material that appears blue in light. It is decomposed by strong acids and alkalis after heating. Beispiel 2 Der Pentafluor-phenyl-thioharnstoff wurde durch Reaktion von Pentafluor-anilin-hydrochloridsalz mit Ammoniumthiocyamat, in konzentrierter Chlorwas- serstoffsäure-Lösung, entsprechend der Gleichung : EMI1.2 hergestellt. Example 2 The pentafluorophenyl thiourea was obtained by reacting pentafluoro aniline hydrochloride salt with ammonium thiocyamate in a concentrated hydrochloric acid solution according to the equation: EMI1.2 manufactured. Zunächst wurde das Chlorwasserstoffsalz von Pentafluor-anilin, durch. Auflöslen von Pentafluor-ani- lin in konzentrierter Chlorwasserstoffsäure bei etwa 80 C erzeugt. Nach Abkühlen auf Zimmertemperatur wurde zu dieser Lösung gemahlenes'Ammonium- thiocyanat hinzugesetzt und das ganze Reaktionsgemisch auf 100 C während 3 Stunden erhitzt. First, the hydrogen chloride salt of pentafluoro aniline was made by. Dissolving pentafluoro-aniline in concentrated hydrochloric acid at about 80 ° C produces. After cooling to room temperature, ground ammonium thiocyanate was added to this solution and the entire reaction mixture was heated to 100 ° C. for 3 hours. Der Gehalt der Flasche wurde : dann bis zur Trockne abge, dampft und in Wasser bei 70 C gelöst. The contents of the bottle were: then evaporated to dryness, evaporated and dissolved in water at 70.degree. Das Produkt schied sich nach Kühlen in feinem kri stallinen Plättchen aus, welche nach Rekristallisiere. n einen F = 151 bis 152 C aufwiesen. After cooling, the product separated out in fine, crystalline platelets, which after recrystallization. n had an F = 151 to 152 C. Der Pe, nbafluor-phenyl-thioharnstoff kristallisiert in matten gelben Plättchen, und ist in Wasser sehr leicht löslich. The Pe, nbafluor-phenyl-thiourea crystallizes in matt yellow flakes and is very easily soluble in water. Es hat sich ergeben, dass beide Verbindungen Eigenschaften für eine Verwendung als Sedativa oder Hypnotika zeigen. Sie können auch Zwischenprodukt bei der Herstellung von tandem, heilkräftigen Verbindungen sein. Both compounds have been found to exhibit properties for use as sedatives or hypnotics. They can also be an intermediate in the making of tandem, medicinal compounds. PATENTANSPRUCH Verfahren zur Herstellung von Pentafluor-phe- nyl-harnstoff bzw.-thioharnstoff, dadurch gekennzeichnet, dass man 2,3,4,5,6-Pentafluor-, anilin mit einer Cyanat-bzw. Thiocyanat-Ionen abgebenden Verbindung in saurer Losung reagieren lässt und dann erhitzt. PATENT CLAIM Process for the production of pentafluorophenyl urea or thiourea, characterized in that 2,3,4,5,6-pentafluoro, aniline with a cyanate or. Thiocyanate ion releasing compound can react in acidic solution and then heated. UNTERANSPRUCH Verfahren nach Patentanspruch, dadurch gekenn- zeichnet, dass man Kalium-oder Ammoniumcyanat bzw.-thiocyanatverwendet. SUBClaim Process according to patent claim, characterized in that potassium or ammonium cyanate or thiocyanate is used.
CH542061A 1960-05-12 1961-05-09 Process for the production of pentafluorophenyl urea or -thiourea CH416595A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB1676760A GB923365A (en) 1960-05-12 1960-05-12 Pentafluorophenyl compounds

Publications (1)

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CH416595A true CH416595A (en) 1966-07-15

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CH (1) CH416595A (en)
FR (1) FR1291887A (en)
GB (1) GB923365A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102649775A (en) * 2011-02-26 2012-08-29 吉木青 Synthetic method of tricyclazole intermediate

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102649775A (en) * 2011-02-26 2012-08-29 吉木青 Synthetic method of tricyclazole intermediate

Also Published As

Publication number Publication date
GB923365A (en) 1963-04-10
FR1291887A (en) 1962-04-27

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