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US4066642A Expired / Lapsed US ⏱️ 0.0 years remaining

Process for the production of thiophosphoric acid esters

Assignee: Novartis Corp
•
Filing: 1976-04-19
•
Granted: 1978-01-03
•
Expires: 1996-04-19
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Abstract

Abstract An improved process for the production of dialkoxy phosphoric acid esters of substituted hydroxypyrimidines which involves reacting a dialkyl phosphoric acid halide with a substituted hydroxypyrimidine at elevated temperatures and in the presence of an inert non-polar organic solvent and an acid binding agent but without catalyst, wherein the phosphoric acid halide and sodium or potassium hydroxide in molar excess of about 5 to 10% are added to a reaction mixture in reflux consisting essentially of the hydroxypyrimidine in molar excess of about 1 to 5% and the non-polar solvent at uniform rates over a period of 1 to 7 hours while removing water substantially as it is formed thereby impeding formation of cholinesterase inhibiting impurities. A preferred embodiment is the preparation of Diazinon.

Inventors

  • 👤 Yel S. Sury
  • 👤 James M. Lignos

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-29 20:12
CPC Classifications
C; C07; C07F; C07F9/00; C07F9/02; C07F9/547; C07F9/645; C07F9/6509; C07F9/6512

Claims Analysis

Total Claims: 4
Claim 1
Independent Claim 208 words
In a process for the production of thiophosphoric acid esters of the formula I ##STR4## wherein R 1 is lower alkyl, lower alkenyl, lower alkoxy(lower)alkyl or lower alkylmercapto(lower)alkyl, R 2 is hydrogen, lower alkyl or lower alkenyl and R 3 and R 4 are lower alkyl, which comprises reacting a dialkyl phosphoric acid halide of the formula II ##STR5## wherein Hal represents chlorine or bromine and R 3 and R 4 are as defined hereinabove, with a hydroxypyrimidine of the formula III ##STR6## wherein R 1 and R 2 have the significance given to them above, at elevated temperatures and in the presence of an organic solvent and an acid binding agent, the improvement which comprises adding the reactant of formula II and sodium or potassium hydroxide concomitantly to a reaction mixture in reflux consisting essentially of reactant of formula III and an inert non-polar organic solvent at uniform rates over a period of 1 to 7 hours while removing water substantially as it is formed, said reactant of formula III being in a molar excess of about 1 to 5% and said acid binding agent being in a molar excess of about 5 to 10%, and said reaction being carried out in the absence of a catalyst.
Claim 2
Dependent Claim 208 words
In a process for the production of thiophosphoric acid esters of the formula I ##STR4## wherein R 1 is lower alkyl, lower alkenyl, lower alkoxy(lower)alkyl or lower alkylmercapto(lower)alkyl, R 2 is hydrogen, lower alkyl or lower alkenyl and R 3 and R 4 are lower alkyl, which comprises reacting a dialkyl phosphoric acid halide of the formula II ##STR5## wherein Hal represents chlorine or bromine and R 3 and R 4 are as defined hereinabove, with a hydroxypyrimidine of the formula III ##STR6## wherein R 1 and R 2 have the significance given to them above, at elevated temperatures and in the presence of an organic solvent and an acid binding agent, the improvement which comprises adding the reactant of formula II and sodium or potassium hydroxide concomitantly to a reaction mixture in reflux consisting essentially of reactant of formula III and an inert non-polar organic solvent at uniform rates over a period of 1 to 7 hours while removing water substantially as it is formed, said reactant of formula III being in a molar excess of about 1 to 5% and said acid binding agent being in a molar excess of about 5 to 10%, and said reaction being carried out in the absence of a catalyst.
Claim 3
Dependent Claim 14 words
A process as claimed in claim 1, wherein the solvent is dichloroethane or trichloroethane.
Claim 4
Dependent Claim 26 words
A process as claimed in claim 1, wherein the reactant of formula II is o,o-diethyl thiophosphoric acid chloride and the reactant of formula III is 2-isopropyl-4-methyl-6-hydroxypyrimidine.

References Cited (Backward Citations)

US2754243A Cited
US3004054A Cited
US3107246A Cited
US3329678A Cited
US3432503A Cited
US3741968A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1981-01-02 1981-07-04 1982-01-03 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1985-01-02 1985-07-04 1986-01-03 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1989-01-02 1989-07-04 1990-01-03 $7700.00 Window Closed / Lapsed

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