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

HRID 647789

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:19](=[S:26])([O:23][CH2:24][CH3:25])[O:20][CH2:21][CH3:22])CC.[N:27]1C=C[CH:30]=[CH:29][CH:28]=1>>[CH2:24]([O:23][P:19]([CH2:30][CH2:29][CH2:28][NH:27][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:20][CH2:21][CH3:22])=[S:26])[CH3:25]

Participants

Reactant 4

HCID 1049Pyridine

HCID 4109Methomyl

HCID 24386Thionyl Chloride

HCID 2172696O,O-diethyl propylphosphoramidothioate

Product 1

HCID 86739074Methyl N-[[[[[(diethoxyphosphinothioyl)propylamino]sulfinyl]methylamino]carbonyl]oxy]ethanimidothioate

Procedure

Methyl N-[[[[[(diethoxyphosphinothioyl)propylamino]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 propylphosphoramidothioate (3.17 g, 0.015 mole) in pyridine (10 ml). Recrystallization from benzene-hexane afforded 3.87 g of colorless prisms of the formula below, mp 58~59°. ##STR26##

Workup

customRecrystallization from benzene-hexane

Sources & evidence

ORD record: ord-9d82e983495342eb853bb716e11d862a
Source dataset: uspto-grants-1983_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04410518

Linked notes

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