CH300740A - Process for producing a phosphoric acid ester. - Google Patents

Process for producing a phosphoric acid ester.

Info

Publication number
CH300740A
CH300740A CH300740DA CH300740A CH 300740 A CH300740 A CH 300740A CH 300740D A CH300740D A CH 300740DA CH 300740 A CH300740 A CH 300740A
Authority
CH
Switzerland
Prior art keywords
methyl
phosphoric acid
acid ester
producing
isopropyl
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
Publication of CH300740A publication Critical patent/CH300740A/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
    • C07F9/6509—Six-membered rings
    • C07F9/6512—Six-membered rings having the nitrogen atoms in positions 1 and 3

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)

Description

  

  Verfahren     zur    Herstellung     eines        Phosphorsäureesters.            Gegenstand        des    vorliegenden Patentes ist  ein Verfahren zur Herstellung eines     Phos-          phorsäureesters.    Das Verfahren ist dadurch  gekennzeichnet, dass man     eine    Verbindung  der Formel  
EMI0001.0009     
         worin.    X Chlor oder Brom bedeutet, mit einer       Verbindung    der Formel  
EMI0001.0012     
    worin Y einen im Verlaufe des Verfahrens  sich abspaltenden Rest; wie Wasserstoff oder  ein Kation, bedeutet,     umsetzt.     



  Die erhaltene neue Verbindung, der     Thio-          phosphorsäure-        [2-isopropyl    - 4 -     methyl-        pyrimi-          dyl-(6)]-n-propyl-methyl-ester,    stellt eine  leicht gefärbte Flüssigkeit dar, die unter  0,2 mm Druck bei 124 bis 126  siedet.  



  Sie soll als Wirksubstanz für Schädlings  bekämpfungsmittel     Verwendung    finden.  <I>Beispiel:</I>  152 Teile     2-Isopropyl-4-methyl-6-oxy-pyri-          midin    werden mit 138 Teilen     Kaliumcarbonat       und 2000 Teilen Benzol versetzt und unter  Rühren zum Sieden erhitzt.

   Dabei wird das  bei der     Enolatbildung    freiwerdende Wasser  mit Benzol     azeotrop        abdestilliert:    Sobald sieh  im     Destillat    kein Wasser mehr abscheidet,  wird auf 60 bis     70     abgekühlt, 190 Teile       n-Propyl-methyl=thiophosphorsäurechlorid    zu  getropft und anschliessend 10 Stunden unter       Rückfluss    gekocht.

   Nach dem Erkalten wird  der     Reaktionsmischung        unter    gutem Rühren  so lange     Kalium        carbonatlösung    .zugesetzt, bis  die     wässrige    Schicht     Phenolphthaleinpapier     eben rot anfärbt.

   Nach     Abtrennen    der     wäss-          rigen    Schicht wird     das        Lösungsmittel        abde-          atilliert.    Es bleibt der     Thiophosphorsäure-          [2    -     isopropyl        ).    4 -     methyl-pyrimidyl-    (6) ] -n     pro-          pyl-methyl-ester    als schwach gefärbte Flüssig  keit zurück, der unter 0,2 min Druck bei 124  bis 126  siedet.



  Process for producing a phosphoric acid ester. The present patent relates to a process for the production of a phosphoric acid ester. The process is characterized in that a compound of the formula
EMI0001.0009
         wherein. X signifies chlorine or bromine with a compound of the formula
EMI0001.0012
    wherein Y is a radical which is split off in the course of the process; such as hydrogen or a cation, means, converts.



  The new compound obtained, the thiophosphoric acid [2-isopropyl - 4 - methylpyrimidyl- (6)] - n-propylmethyl ester, is a lightly colored liquid that can be used under 0.2 mm pressure boils at 124 to 126.



  It should be used as an active ingredient for pesticides. <I> Example: </I> 152 parts of 2-isopropyl-4-methyl-6-oxy-pyrimidine are mixed with 138 parts of potassium carbonate and 2000 parts of benzene and heated to the boil with stirring.

   The water released during enolate formation is azeotropically distilled off with benzene: As soon as no more water separates out in the distillate, the mixture is cooled to 60 to 70, 190 parts of n-propyl-methyl = thiophosphoric acid chloride are added dropwise and then refluxed for 10 hours.

   After cooling, the reaction mixture is added with potassium carbonate solution with thorough stirring until the aqueous layer of phenolphthalein paper just stains red.

   After the aqueous layer has been separated off, the solvent is distilled off. It remains the thiophosphoric acid [2 - isopropyl). 4 - methyl-pyrimidyl- (6)] -n propyl-methyl-ester returns as a weakly colored liquid which boils at 124 to 126 under a pressure of 0.2 min.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines Phos- phorsäureesters, dadurch gekennzeichnet, dass man eine Verbindung der Formel EMI0001.0055 worin X Chlor oder Brom bedeutet, mit einer Verbindung der Formel EMI0002.0001 worin Y einen im Verlaufe des Verfahrens sich abspaltenden Rest bedeutet, umsetzt. PATENT CLAIM: Process for the production of a phosphoric acid ester, characterized in that a compound of the formula EMI0001.0055 wherein X is chlorine or bromine, with a compound of the formula EMI0002.0001 where Y is a radical which is split off in the course of the process. Die erhaltene neue Verbindung, der Thio- phosphorsäure- [2- isopropyl- 4 -methyl-pyrimi- dyl-(6)]-n-propyl-methyl-ester, stellt eine leicht gefärbte Flüssigkeit dar, die unter 0,2 mm Druck bei 124 bis 126 siedet. UNTERANSPRUCH: Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man ein Alkalisalz des 2 - Isopropyl- 4 -methyl - 6 - oxy-pyrimidins mit n-Propyl-methyl-thiophosphorsäurechlorid um setzt. The new compound obtained, the thiophosphoric acid [2-isopropyl-4-methyl-pyrimidyl- (6)] -n-propyl-methyl ester, is a slightly colored liquid that can be used under 0.2 mm pressure boils at 124 to 126. SUBSTANTIAL CLAIM: Process according to patent claim, characterized in that an alkali salt of 2 - isopropyl-4-methyl-6-oxy-pyrimidine is reacted with n-propyl-methyl-thiophosphoric acid chloride.
CH300740D 1951-04-20 1951-04-20 Process for producing a phosphoric acid ester. CH300740A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH294598T 1951-04-20
CH300740T 1951-04-20

Publications (1)

Publication Number Publication Date
CH300740A true CH300740A (en) 1954-08-15

Family

ID=25733501

Family Applications (1)

Application Number Title Priority Date Filing Date
CH300740D CH300740A (en) 1951-04-20 1951-04-20 Process for producing a phosphoric acid ester.

Country Status (1)

Country Link
CH (1) CH300740A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3981993A (en) 1974-03-28 1976-09-21 Bayer Aktiengesellschaft O-Alkyl-O-n-propyl-O-pyrimidin(2)yl-thiono-phosphoric acid esters
US4093718A (en) 1975-02-22 1978-06-06 Bayer Aktiengesellschaft O,O-dialkyl-5-halo-pyrimidin(2) yl-thionophosphoric acid esters

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3981993A (en) 1974-03-28 1976-09-21 Bayer Aktiengesellschaft O-Alkyl-O-n-propyl-O-pyrimidin(2)yl-thiono-phosphoric acid esters
US4093718A (en) 1975-02-22 1978-06-06 Bayer Aktiengesellschaft O,O-dialkyl-5-halo-pyrimidin(2) yl-thionophosphoric acid esters

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