Process for preparing phosphorothioates and phenylphosphonothioa

Organic compounds -- part of the class 532-570 series – Organic compounds – Four or more ring nitrogens in the bicyclo ring system

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2602948K, 260973, 544337, C07F 909, C07F 9165

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active

040923126

ABSTRACT:
Mixtures of (1) a quaternary ammonium salt(s) and (2) 1,4-diazabicyclo[2.2.2]octane are novel catalysts in the process of reacting an alkali metal phenate, pyridinate or pyrimidinate with an O,O-dialkyl phosphorochloridothioate or O-alkyl phenylphosphonochloridothioate to produce the corresponding phosphorothioates and phenylphosphonothioates. The process is conducted under alkaline conditions in a liquid reaction medium. As an example, O,O-diethyl O-(3,5,6-trichloro-2-pyridyl)phosphorothioate is prepared in excellent yields and purity by reacting sodium 3,5,6-trichloropyridinate with O,O-diethyl phosphorochloridothioate in a stirred methylene chloride-water reaction medium in the presence of a catalytic amount of benzyltriethylammonium chloride and 1,4-diazabicyclo[2.2.2]octane.

REFERENCES:
patent: 3244586 (1966-04-01), Rigterink
patent: 3792132 (1974-02-01), Bernhart
patent: 3907815 (1975-09-01), Kroposki et al.
patent: 3972887 (1976-08-01), Freedman
patent: 4016225 (1977-04-01), Kroposki et al.

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