CH281950A - Process for the preparation of a heterocyclic carbamic acid derivative. - Google Patents

Process for the preparation of a heterocyclic carbamic acid derivative.

Info

Publication number
CH281950A
CH281950A CH281950DA CH281950A CH 281950 A CH281950 A CH 281950A CH 281950D A CH281950D A CH 281950DA CH 281950 A CH281950 A CH 281950A
Authority
CH
Switzerland
Prior art keywords
sep
acid derivative
carbamic acid
preparation
heterocyclic
Prior art date
Application number
Other languages
German (de)
Inventor
Ag J R Geigy
Original Assignee
Ag J R Geigy
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 J R Geigy filed Critical Ag J R Geigy
Priority claimed from GB3001049A external-priority patent/GB681376A/en
Publication of CH281950A publication Critical patent/CH281950A/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D277/34—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D249/12—Oxygen or sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/34—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D309/36—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Description

  

  Verfahren zur Herstellung eines     heterocyclischen        Carbaminsäurederivates.       Gegenstand vorliegenden Patentes ist ein  Verfahren zur     Herstellung    eines     het.erocycli-          schen        Carbaminsäurederivates.    Das Verfahren  ist     dadurch        -ekennzeichnet,    dass man eile     Ver-          binduiig    der Formel  
EMI0001.0011     
    mit einem     Carbonsäurederivat    der Formel  
EMI0001.0013     
    umsetzt,

   worin     Y    und V     zwei    sich im Verlaufe  des Verfahrens abspaltende Reste     bedeuten.     



  Die erhaltene neue Verbindung, das     1-Phe-          nyl-3-methyl-1,2,4-triazolyl-    (5     )-climethy        learba-          mat,    siedet unter 0,12 mm Druck bei 1.70 bis  172 . Sie soll. als Wirkstoff für Schädlings  bekämpfungsmittel Verwendung finden.  



  <I>Beispiel:</I>  16 Teile     1-Phenyl-3-methyl-1,2,4-triazolon-          (51werden    mit. 7 Teilen     Kalüunkarbonat    und  200 Teilen Benzol an einem     Rüeldlusskühler     mit     -V        asserabscheider    so lange erhitzt, bis kein  Wasser mehr übergebt. Dann kühlt man das  Reaktionsgemisch etwas ab und gibt 12 Teile         Dimethylcarbaminsäurechlorid    hinzu. Durch  Erhitzen zum     Rückfluss    über Nacht wird die  Reaktion vervollständigt.

   Um eventuell nicht  umgesetztes     Triazolon    zu entfernen, wird die  erkaltete     benzolische    Lösung mit     Kaliumkar-          bonatlösung    durchgerührt, die     benzolische     Schicht abgehoben, mit Wasser     neutralgewa-          schen    und getrocknet. Nach Entfernung des  Lösungsmittels wird der Rückstand durch De  stillation im Hochvakuum gereinigt.

   Das     1-          Phenyl    - 3 -     methyl-1,2,4-triazolyl-    (5)     -dimethyl-          carbamat    siedet bei 170 bis 172  und 0,12 mm  und erstarrt zu einer farblosen Kristallmasse,  die, aus     Cyclohexan    umkristallisiert, einen  Schmelzpunkt von 72 bis 73  zeigt.



  Process for the preparation of a heterocyclic carbamic acid derivative. The present patent relates to a process for the production of a heterocyclic carbamic acid derivative. The method is characterized by the fact that the formula is quickly connected
EMI0001.0011
    with a carboxylic acid derivative of the formula
EMI0001.0013
    implements,

   where Y and V are two radicals which are split off in the course of the process.



  The new compound obtained, the 1-phenyl-3-methyl-1,2,4-triazolyl- (5) -climethy learba- mat, boils under 0.12 mm pressure at 1.70 to 172. She should. find use as an active ingredient for pesticides.



  <I> Example: </I> 16 parts of 1-phenyl-3-methyl-1,2,4-triazolon- (51 are heated with 7 parts of potassium carbonate and 200 parts of benzene in a flow condenser with water separator until The reaction mixture is then cooled somewhat, 12 parts of dimethylcarbamic acid chloride are added and the reaction is completed by heating to reflux overnight.

   In order to remove any unreacted triazolone, the cooled benzene solution is stirred with potassium carbonate solution, the benzene layer is lifted off, washed neutral with water and dried. After removing the solvent, the residue is purified by distillation in a high vacuum.

   The 1-phenyl - 3 - methyl-1,2,4-triazolyl (5) -dimethyl carbamate boils at 170 to 172 and 0.12 mm and solidifies to a colorless crystal mass which, recrystallized from cyclohexane, has a melting point of 72 to 73 shows.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines hetero- cyelischen Carbaminsäurederivates, dadurch gekennzeichnet, dass man eine Verbindung der Formel EMI0001.0047 mit. einem CarbaminsäureAerivat der Formel EMI0001.0049 EMI0002.0001 umsetzt, <SEP> worin <SEP> X <SEP> und <SEP> Y <SEP> zwei <SEP> sich <SEP> im <SEP> Verlaufe <tb> des <SEP> Verfahrens <SEP> abspaltende <SEP> Reste <SEP> bedeuten. <tb> Die <SEP> erhaltene <SEP> neue <SEP> Verbindung, <SEP> das <SEP> 1.-Phe ny <SEP> 1-3-m <SEP> eth-#rl-1.,2,.1-triazol <SEP> y1- <SEP> (5) <SEP> -dimethylcarba mat, <SEP> siedet <SEP> unter <SEP> 0,12 <SEP> mm <SEP> Druek <SEP> bei <SEP> 170 <SEP> bis <tb> 172 . PATENT CLAIM: Process for the preparation of a heterocyclic carbamic acid derivative, characterized in that a compound of the formula EMI0001.0047 With. a carbamic acid derivative of the formula EMI0001.0049 EMI0002.0001 implements, <SEP> where <SEP> X <SEP> and <SEP> Y <SEP> two <SEP> are <SEP> in the <SEP> course <tb> of the <SEP> process <SEP> means <SEP> separating residues <SEP>. <tb> The <SEP> received <SEP> new <SEP> connection, <SEP> the <SEP> 1.-Phe ny <SEP> 1-3-m <SEP> eth- # rl-1., 2, .1-triazole <SEP> y1- <SEP> (5) <SEP> -dimethylcarba mat, <SEP> boils <SEP> under <SEP> 0.12 <SEP> mm <SEP> pressure <SEP> at <SEP > 170 <SEP> to <tb> 172. EMI0002.0002 UNTERANSPRUCFI <tb> Verfahren <SEP> nach <SEP> Patentansprueh, <SEP> dadureh <tb> gekennzeichnet, <SEP> dass <SEP> man <SEP> ein <SEP> Alkalisalz <SEP> des <SEP> 1 Phenyl-3-nnethyl-1,2,4-triazolons-(5) <SEP> mit <SEP> einem <tb> Dimethylear-baminsäurehalogenid <SEP> umsetzt. EMI0002.0002 UNDER CLAIMS <tb> Method <SEP> according to <SEP> patent claim, <SEP> dadureh <tb>, <SEP> that <SEP> one <SEP> is a <SEP> alkali salt <SEP> of <SEP> 1 phenyl-3-methyl-1,2,4-triazolons- (5) <SEP> with <SEP> one <tb> Dimethylearbamic acid halide <SEP> converts.
CH281950D 1949-08-22 1949-08-26 Process for the preparation of a heterocyclic carbamic acid derivative. CH281950A (en)

Applications Claiming Priority (7)

Application Number Priority Date Filing Date Title
CH2681915X 1949-08-22
CH2681879X 1949-08-22
CH2694712X 1949-08-22
CH2681914X 1949-08-22
CH2681916X 1949-08-22
CH281950T 1949-08-26
GB3001049A GB681376A (en) 1949-11-23 1949-11-23 Manufacture of heterocyclic carbamic acid derivatives and their use as agents for combating pests

Publications (1)

Publication Number Publication Date
CH281950A true CH281950A (en) 1952-03-31

Family

ID=32303871

Family Applications (1)

Application Number Title Priority Date Filing Date
CH281950D CH281950A (en) 1949-08-22 1949-08-26 Process for the preparation of a heterocyclic carbamic acid derivative.

Country Status (1)

Country Link
CH (1) CH281950A (en)

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