CH281963A - 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
CH281963A
CH281963A CH281963DA CH281963A CH 281963 A CH281963 A CH 281963A CH 281963D A CH281963D A CH 281963DA CH 281963 A CH281963 A CH 281963A
Authority
CH
Switzerland
Prior art keywords
sep
carbamic acid
acid derivative
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 CH281963A publication Critical patent/CH281963A/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
    • C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D271/10—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles
    • C07D271/113—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
    • 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
    • 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
    • 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

Description

  

  <B>Verfahren zur Herstellung eines</B>     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  
EMI0001.0006     
    mit einem     Carbaminsäurederivat    der Formel  
EMI0001.0008     
    umsetzt, worin     .K    und Y zwei sich im Verlaufe  des Verfahrens abspaltende Reste bedeuten.  



  Die erhaltene neue Verbindung, das     2-Me-          thyl    -1,3,4 -     oxdiazolyl    - (5) -     dimethylcarbamat,     zeigt einen Schmelzpunkt von 73 bis 74 . Sie  soll als Wirkstoff für Schädlingsbekämpfungs  mittel Verwendung finden.  



  <I>Beispiel:</I>  95 Teile     2-Methyl-5-oxy-1,3,4-oxdiazol    wer  den mit 600 Teilen Benzol und 135 Teilen     Ka-          liumcarbonat    unter Rühren     zum    Sieden erhitzt  und so lange Benzol     abdestilliert,    bis kein Was  ser mehr übergeht. Das Gemisch wird abge  kühlt und dann mit 120 Teilen     Dimethyl-          earbaminsäurechlorid    versetzt. Dabei ist Sorge  zu tragen, dass die Reaktion nicht zu stürmisch    verläuft, was gegebenenfalls durch Kühlen  erreicht 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     phenolphthaleinalkalisch    bleibt.

   Nach  Abtrennen des wässerigen Teils wird die     ben-          zolische    Lösung mit Wasser bis zur neutralen  Reaktion     gewaschen,    dann das Benzol     abdestil-          liert.    Das     2-lIethyl-1,3,4-oxdiazolyl-(5)-dime-,          thylcarbamat    zeigt einen Schmelzpunkt von  73 bis 74 .



  <B> Process for the production of </B> 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
EMI0001.0006
    with a carbamic acid derivative of the formula
EMI0001.0008
    converts, wherein .K and Y are two radicals split off in the course of the process.



  The new compound obtained, the 2-methyl -1,3,4 - oxdiazolyl - (5) - dimethyl carbamate, has a melting point of 73 to 74. It should be used as an active ingredient for pest control agents.



  <I> Example: </I> 95 parts of 2-methyl-5-oxy-1,3,4-oxdiazole are heated to the boil with 600 parts of benzene and 135 parts of potassium carbonate while stirring and benzene is distilled off until no more water passes over. The mixture is cooled and then treated with 120 parts of dimethyl earbamic acid chloride. 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 so much conc. Potash solution added that the reaction of the aqueous solution after shaking with the benzene layer remains clearly phenolphthalein alkaline.

   After the aqueous part has been separated off, the benzene solution is washed with water until the reaction is neutral, then the benzene is distilled off. The 2-ethyl-1,3,4-oxdiazolyl- (5) -dimethylcarbamate has a melting point of 73 to 74.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines hetero- cyclischen Carbaminsäurederivates, dadurch gekennzeichnet, da.ss man eine Verbindung der Formel EMI0001.0038 mit einem Carbaminsäurederivat der Formel EMI0001.0040 umsetzt, worin Y und Y zwei sich im Verlaufe des Verfahrens abspaltende Reste bedeuten. Die erhaltene neue Verbindung, das 2-Me- thy1-1,3,4-oxdia.zolyl:- (5) -dimethylcarbamat, <B>5</B> zeigt einen Schmelzpunkt von 73 bis 74 . PATENT CLAIM: Process for the preparation of a heterocyclic carbamic acid derivative, characterized in that one is a compound of the formula EMI0001.0038 with a carbamic acid derivative of the formula EMI0001.0040 converts, in which Y and Y are two radicals split off in the course of the process. The new compound obtained, 2-methy1-1,3,4-oxdia.zolyl: - (5) -dimethylcarbamate, <B> 5 </B> has a melting point of 73 to 74. EMI0002.0007 UN <SEP> TERAN <SEP> SPRC: <SEP> CII <tb> Verfahren <SEP> naeh <SEP> Patezitanspruch, <SEP> dadurch <tb> gekennzeichnet, <SEP> da.ss <SEP> man <SEP> ein <SEP> Alkalisalz <SEP> des <tb> 2-IVIethyl-5-oxy-1,3,4-oxdiazols <SEP> mit <SEP> Dimethyl carbaminsäurechlorid <SEP> umsetzt. EMI0002.0007 UN <SEP> TERAN <SEP> SPRC: <SEP> CII <tb> Procedure <SEP> after <SEP> patent claim, <SEP> thereby <tb> marked, <SEP> da.ss <SEP> man <SEP> a <SEP> alkali salt <SEP> des <tb> 2-IVIethyl-5-oxy-1,3,4-oxdiazoles <SEP> with <SEP> dimethyl carbamic acid chloride <SEP>.
CH281963D 1949-08-22 1949-08-26 Process for the preparation of a heterocyclic carbamic acid derivative. CH281963A (en)

Applications Claiming Priority (7)

Application Number Priority Date Filing Date Title
CH2694712X 1949-08-22
CH2681914X 1949-08-22
CH2681879X 1949-08-22
CH2681916X 1949-08-22
CH2681915X 1949-08-22
CH281963T 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
CH281963A true CH281963A (en) 1952-03-31

Family

ID=32303879

Family Applications (1)

Application Number Title Priority Date Filing Date
CH281963D CH281963A (en) 1949-08-22 1949-08-26 Process for the preparation of a heterocyclic carbamic acid derivative.

Country Status (1)

Country Link
CH (1) CH281963A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1020633B (en) * 1953-05-15 1957-12-12 Pennsylvania Salt Mfg Co Process for the preparation of derivatives of 2,5-dimercapto-1,3-, 4-thiadiazole
DE1023038B (en) * 1953-05-28 1958-01-23 Pennsylvania Salt Mfg Co Process for the preparation of 1, 3, 4-thiodiazoles

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1020633B (en) * 1953-05-15 1957-12-12 Pennsylvania Salt Mfg Co Process for the preparation of derivatives of 2,5-dimercapto-1,3-, 4-thiadiazole
DE1023038B (en) * 1953-05-28 1958-01-23 Pennsylvania Salt Mfg Co Process for the preparation of 1, 3, 4-thiodiazoles

Similar Documents

Publication Publication Date Title
CH281963A (en) Process for the preparation of a heterocyclic carbamic acid derivative.
DE2942140A1 (en) METHOD FOR PRODUCING SUBSTITUTED PYRROL DIESTERS
CH281952A (en) Process for the preparation of a heterocyclic carbamic acid derivative.
CH281965A (en) Process for the preparation of a heterocyclic carbamic acid derivative.
CH281968A (en) Process for the preparation of a heterocyclic carbamic acid derivative.
CH282252A (en) Process for the preparation of a heterocyclic carbamic acid derivative.
CH281957A (en) Process for the preparation of a heterocyclic carbamic acid derivative.
CH300741A (en) Process for producing a phosphoric acid ester.
CH300748A (en) Process for producing a phosphoric acid ester.
CH232273A (en) Process for the production of a cyclopentano-dimethyl-polyhydro-phenanthrene-carboxylic acid.
CH300758A (en) Process for producing a phosphoric acid ester.
CH281955A (en) Process for the preparation of a heterocyclic carbamic acid derivative.
CH300760A (en) Process for producing a phosphoric acid ester.
CH300744A (en) Process for producing a phosphoric acid ester.
CH306793A (en) Process for making a new salt.
CH300739A (en) Process for producing a phosphoric acid ester.
CH300738A (en) Process for producing a phosphoric acid ester.
CH300742A (en) Process for producing a phosphoric acid ester.
CH311558A (en) Process for the production of a new basic substituted fatty acid amide.
CH313373A (en) Process for the preparation of crystallized cyclohexyl peroxides
CH141455A (en) Process for the preparation of an o-aminoarylrhodane compound.
CH281964A (en) Process for the preparation of a heterocyclic carbamic acid derivative.
CH300757A (en) Process for producing a phosphoric acid ester.
CH304557A (en) Process for the preparation of a new tetrahydropyridine.
CH370065A (en) Process for the production of D-ascorbic acid