Methanol → Diethyl 3-(N-Hydroxyamino)propylphosphate

Firstly 32.0 g (0.8 mol) of sodium hydroxide dissolved in 75 ml water then 75 ml methanol, and finally 25.5 g (0.098 mol) 3-bromopropyl phosphonic acid diethylester were added drop by drop to a solution of 55.6 g (0.8 mol) hydroxylamine hydrochloride in 100 ml water with cooling with ice. This led to a clouding of the solution. After 3 hours stirring at a temperature of 40 to 45° C. methanol was removed under reduced pressure, the resulting aqueous solution was saturated with NaHCO3 (pH=8), shaken out three times with 60 ml toluene in each case (the toluene phase was discarded) and then shaken out with chloroform (1× with 90 ml, 2× with 50 ml in each case). The slightly yellowy chloroform phase was dried over MgSO4. After filtering of the dehydrating agent the solution was concentrated under reduced pressure. 15.43 g (0.0728 mol) 3-(N-hydroxyamino)-propylphosphonic acid diethylester were obtained as an almost colourless oil. This corresponds to a yield of 74.3% (DE-A-27 33 658).

1. temperaturewith cooling with ice
2. customwas removed under reduced pressure
3. stirringthen shaken out with chloroform (1× with 90 ml, 2× with 50 ml in each case)
4. dry with materialThe slightly yellowy chloroform phase was dried over MgSO4
5. filtrationAfter filtering of the dehydrating agent the solution
6. concentrationwas concentrated under reduced pressure

ORD-Eintrag

ord-4b8f464720ae403aa64e018e5ada8618

Quelldatensatz

uspto-grants-2004_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06680308B1