Methyl iodide → Diethyl ({[(methylsulfanyl)carbonothioyl]amino}methyl)phosphonate

Carbon disulfide (0.88 ml, 1.11 g) was added dropwise to a stirred solution of 2.45 g (14.6 mmol) of diethyl aminomethylphosphonate and 0.82 g (14.6 mmol) of potassium hydroxide in 25 ml of ethanol. During addition the temperature of the reaction mixture rose from 26° to 33°. A second portion of 0.88 ml of carbon disulfide was added and the mixture was stirred at 50° for 1 hour. The mixture was cooled to ambient temperature, 2.08 g (14.6 mmol) of methyl iodide was added dropwise and the resulting mixture was stirred for 1.5 hours. The mixture was evaporated to dryness, the residue was dissolved in water and the aqueous solution was extracted twice with ethyl acetate. The extracts were combined, dried (MgSO4) and evaporated to dryness to give methyl 1-diethoxyphosphinylmethyldithiocarbamate.

1. additionDuring addition the temperature of the reaction mixture
2. customrose from 26° to 33°
3. stirringthe resulting mixture was stirred for 1.5 hours
4. customThe mixture was evaporated to dryness
5. dissolutionthe residue was dissolved in water
6. extractionthe aqueous solution was extracted twice with ethyl acetate
7. dry with materialdried (MgSO4)
8. customevaporated to dryness

ORD record

ord-76d02733418e4883a283cf2b56dd5446

Source dataset

uspto-grants-1980_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04211703