Sodium Chloride → S-[(Diethoxyphosphoryl)methyl] ethanethioate

HRID 1978368Notes

Reaction equation

Cl[CH2:2][P:3](=[O:10])([O:7][CH2:8][CH3:9])[O:4][CH2:5][CH3:6].[C:11]([O-:14])(=[S:13])[CH3:12].[K+].[Cl-].[Na+]>CN(C)C=O.O>[C:11]([S:13][CH2:2][P:3]([O:7][CH2:8][CH3:9])([O:4][CH2:5][CH3:6])=[O:10])(=[O:14])[CH3:12]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 17.527 g (93.938 mM) of diethyl chloromethylphosphonate in 50 ml of N,N-dimethylformamide was added 12.9 g (113 mM) of potassium thioacetate and the mixture was stirred at 100° C. for 3 hours. This reaction mixture was poured in water, saturated with sodium chloride, and extracted with 4 portions of ethyl acetate. The organic layers were pooled and dried over MgSO4 and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate:3/1 to 1/1) to provide the title compound.

Workup

extractionextracted with 4 portions of ethyl acetate
dry with materialdried over MgSO4
distillationthe solvent was distilled off under reduced pressure
customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate:3/1 to 1/1)

Sources & evidence

ORD record: ord-6eb2c8e3688544a9878cf83dfabbd033
Source dataset: uspto-grants-2001_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06235731B1

Reaction notes

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