Triethylamine → Diethyl 2-(chlorosulfonylamino)ethylphosphonate

Temperature

0 °C

Into a 100-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of sulfuryl dichloride (1.1 g, 8.15 mmol, 1.47 equiv) in dichloromethane (10 mL). This was followed by the addition of a solution of diethyl 2-aminoethylphosphonate (intermediate 1.9) (1.0 g, 5.52 mmol, 1.00 equiv) and triethylamine (800 mg, 7.92 mmol, 1.43 equiv) in dichloromethane (20 mL) dropwise with stirring at 0° C. The resulting solution was stirred for 2 h at 0° C. The reaction was then quenched by the addition of ice water. The organic layer was washed with saturated sodium chloride (20 mL), dried over anhydrous sodium sulfate and concentrated under vacuum. This resulted in 0.5 g (crude) of the title compound as a colorless oil.

1. customInto a 100-mL round-bottom flask purged
2. temperaturemaintained with an inert atmosphere of nitrogen
3. stirringThe resulting solution was stirred for 2 h at 0° C
4. customThe reaction was then quenched by the addition of ice water
5. washThe organic layer was washed with saturated sodium chloride (20 mL)
6. dry with materialdried over anhydrous sodium sulfate
7. concentrationconcentrated under vacuum

ORD record

ord-d60148665bbc415a9121d782c3cf3426

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09408840B2