CH281968A - 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
CH281968A
CH281968A CH281968DA CH281968A CH 281968 A CH281968 A CH 281968A CH 281968D A CH281968D A CH 281968DA CH 281968 A CH281968 A CH 281968A
Authority
CH
Switzerland
Prior art keywords
acid derivative
carbamic acid
preparation
heterocyclic
formula
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 CH281968A publication Critical patent/CH281968A/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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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
    • C07D333/30—Hetero atoms other than halogen
    • C07D333/32—Oxygen atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Description

  

  Verfahren zur Herstellung eines     heterocyclischen        Carbaminsäurederivates.       Gegenstand vorliegenden Patentes ist ein  Verfahren     zur    Herstellung eines     heterocycli-          schen        Carbaminsäurederivates.    Das Verfahren  ist dadurch gekennzeichnet, dass man eine Ver  bindung der Formel  
EMI0001.0007     
    mit einem     Carbaminsäurederivat    der Formel  
EMI0001.0009     
    umsetzt, worin X und Y zwei sich im Verlaufe       (]es    Verfahrens     abspaltende    Reste bedeuten.  



  Die erhaltene neue Verbindung, das     2-Me-          tliyl-thienyl-(5)-dimethylcarbamat,    siedet un  ter 0,03 mm Druck bei 89 bis 90 . Sie soll als  Wirkstoff für     Schädlingsbekämpfungsmittel     Verwendung finden.         Beispiel:       175 Teile     2-Methyl-5-oxy-thiophen    werden  mit. 600 Teilen     Benzol    und 135 Teilen     Kalium-          earbonat    unter Rühren zum Sieden erhitzt       und    so lange Benzol     abdestilliert,    bis kein       Wasser    mehr übergeht.

   Das Gemisch wird ab  gekühlt und dann mit. 120 Teilen     Dimethyl-          earbaminsäurechlorid    versetzt. Dabei ist Sorge       zii    tragen, dass die Reaktion nicht zu stürmisch    verläuft, was     gegebenenfalls    durch Kühlen er  reicht wird. Wenn die Reaktion abgeklungen  ist, wird 10 bis 12 Stunden zum Sieden erhitzt,  wobei sich bildendes Wasser in einem     Abschei-          der    entfernt wird.

   Dann wird .das Reaktions  gemisch abgekühlt, mit 400 Teilen Wasser und  so viel     konz.        Pottaschelösung    versetzt, dass die  Reaktion der wässerigen Lösung nach dem  Durchschütteln mit der     benzolischen    Schicht  deutlich     phenolphthaleinalkaliseh    bleibt. Nach  Abtrennen des wässerigen     Teils    wird die     ben-          zolische    Lösung mit Wasser bis zur neutralen       Reaktion    gewaschen,     dann    das Benzol ab  destilliert.

   Das     2-Methyl-thienyl-(5)-dimethyl-          carbamat    siedet. unter 0,03 mm Druck bei 89       bis    90 .



  Process for the preparation of a heterocyclic carbamic acid derivative. The present patent relates to a process for the preparation of a heterocyclic carbamic acid derivative. The method is characterized in that one is a compound of the formula
EMI0001.0007
    with a carbamic acid derivative of the formula
EMI0001.0009
    converts, in which X and Y are two radicals split off in the course of the process.



  The new compound obtained, 2-methylthienyl (5) -dimethylcarbamate, boils at 89 to 90 under 0.03 mm pressure. It should be used as an active ingredient for pesticides. Example: 175 parts of 2-methyl-5-oxy-thiophene are mixed with. 600 parts of benzene and 135 parts of potassium carbonate are heated to boiling with stirring and benzene is distilled off until no more water passes over.

   The mixture is cooled off and then with. 120 parts of dimethyl earbamic acid chloride are added. Care must be taken that the reaction does not proceed too stormy, which can be achieved by cooling if necessary. When the reaction has subsided, the mixture is heated to the boil for 10 to 12 hours, with any water that forms being removed in a separator.

   Then. The reaction mixture is cooled, with 400 parts of water and as much conc. Potash solution added that the reaction of the aqueous solution after shaking with the benzene layer remains clearly phenolphthalein alkali. After separating off the aqueous part, the benzene solution is washed with water until a neutral reaction is obtained, then the benzene is distilled off.

   The 2-methyl-thienyl- (5) -dimethyl-carbamate boils. under 0.03 mm pressure at 89 to 90.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines hetero- cyclischen Carbaminsäurederivates, dadurch gekennzeichnet, da.ss man eine Verbindung der Formel EMI0001.0045 0 mit einem Carbaminsäurederivat der Formel EMI0001.0047 umsetzt, worin X und Y zwei sich im Verlaufe des Verfahrens abspaltende Reste bedeuten. Die erhaltene neue Verbindung, das 2-Me- thyl-thienyl-(5)-dimethylcarbamat, siedet un ter 0,03 mm Druck bei 89 bis 90 . PATENT CLAIM: Process for the preparation of a heterocyclic carbamic acid derivative, characterized in that one is a compound of the formula EMI0001.0045 0 with a carbamic acid derivative of the formula EMI0001.0047 converts, where X and Y are two radicals split off in the course of the process. The new compound obtained, 2-methylthienyl- (5) -dimethylcarbamate, boils at 89 to 90 under 0.03 mm pressure. UNTERANSPRUCH: Verfahren nach Patentanspruch, dadurch jekennzeichnet, dass man ein Alkalisalz des 2-Methyl-5-oxy-thiophens mit Dimethylcarb- aminsäurechlorid umsetzt. SUBCLAIM: Process according to claim, characterized in that an alkali salt of 2-methyl-5-oxy-thiophene is reacted with dimethylcarbamic acid chloride.
CH281968D 1949-08-22 1949-08-26 Process for the preparation of a heterocyclic carbamic acid derivative. CH281968A (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
CH281968T 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
CH281968A true CH281968A (en) 1952-03-31

Family

ID=32303883

Family Applications (1)

Application Number Title Priority Date Filing Date
CH281968D CH281968A (en) 1949-08-22 1949-08-26 Process for the preparation of a heterocyclic carbamic acid derivative.

Country Status (1)

Country Link
CH (1) CH281968A (en)

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