Pyridine → Methyl N-[[[[[(diethoxyphosphinothioyl)ethylamino]sulfinyl]methylamino]carbonyl]oxy]ethanimidothioate

HRID 647788Notes

Reaction equation

[CH3:1][NH:2][C:3]([O:5][N:6]=[C:7]([S:9][CH3:10])[CH3:8])=[O:4].[S:11](Cl)(Cl)=[O:12].C(N[P:18](=[S:25])([O:22][CH2:23][CH3:24])[O:19][CH2:20][CH3:21])C.[N:26]1C=CC=[CH:28][CH:27]=1>>[CH2:23]([O:22][P:18]([CH2:28][CH2:27][NH:26][S:11]([CH2:1][NH:2][C:3]([O:5][N:6]=[C:7]([S:9][CH3:10])[CH3:8])=[O:4])=[O:12])([O:19][CH2:20][CH3:21])=[S:25])[CH3:24]

Participants

Reactant 4

HCID 1049Pyridine

HCID 4109Methomyl

HCID 24386Thionyl Chloride

HCID 352352O,O-Diethyl N-ethylphosphoramidothioate

Product 1

HCID 86739073Methyl N-[[[[[(diethoxyphosphinothioyl)ethylamino]sulfinyl]methylamino]carbonyl]oxy]ethanimidothioate

Procedure

Methyl N-[[[[[(diethoxyphosphinothioyl)ethylamino]sulfinyl]methylamino]carbonyl]oxy]ethanimidothioate was prepared by the procedure employed in Example 9, by reacting methyl N-[[(methylamino)carbonyl]oxy]ethanimidothioate (2.43 g, 0.015 mole), thionyl chloride (1.79 g, 0.015 mole), and O,O-diethyl ethylphosphoramidothioate (2.96 g, 0.015 mole) in pyridine (10 ml). Recrystallization from chloroform-hexane afforded 2.95 g of colorless prisms of the formula below, mp 67~68°. ##STR25##

Workup

customRecrystallization from chloroform-hexane

Sources & evidence

ORD record: ord-3e866b333c244192bacb55b5ff56d21b
Source dataset: uspto-grants-1983_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04410518

Reaction notes

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