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

HRID 647787Notes

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].CN[P:17](=[S:24])([O:21][CH2:22][CH3:23])[O:18][CH2:19][CH3:20].[N:25]1C=CC=C[CH:26]=1>>[CH2:22]([O:21][P:17]([CH2:26][NH:25][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:18][CH2:19][CH3:20])=[S:24])[CH3:23]

Participants

Reactant 4

HCID 1049Pyridine

HCID 4109Methomyl

HCID 24386Thionyl Chloride

HCID 759370O,O-diethyl methylamidothiophosphate

Product 1

HCID 86739072Methyl N-[[[[[(diethoxyphosphinothioyl)methylamino]sulfinyl]methylamino]carbonyl]oxy]ethanimidothioate

Procedure

Methyl N-[[[[[(diethoxyphosphinothioyl)methylamino]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 methylphosphoramidothioate (2.75 g, 0.015 mole) in pyridine (10 ml). Recrystallization from chloroformhexane afforded 2.75 g of colorless prisms of the formula below, mp 78~78.5°. ##STR24##

Workup

customRecrystallization from chloroformhexane

Sources & evidence

ORD record: ord-265b5a901a7441c6a088e0deb982ff31
Source dataset: uspto-grants-1983_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04410518

Reaction notes

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