Chloroacetyl chloride → HCID 20185730, compound

Participants

Reaction Conditions

Reaction Steps

Chloroacetyl chloride (4.52 g.) was added dropwise to a solution of 3-(N-hydroxyamino)propylphosphonic acid (2.46 g.) in a mixture of water (15 ml.) and acetone (15 ml.) over a 20 minutes-interval with stirring under ice-cooling and maintaining the pH at around 7-8 by adding 5% aqueous sodium bicarbonate solution. After stirring for further hour, the reaction mixture was adjusted to pH 9 with 1 N aqueous sodium hydroxide solution and stirred at ambient temperature for 35 minutes. After acetone was distilled off under reduced pressure, the aqueous solution was acidified to pH 1.8 with 10% hydrochloric acid and evaporated to dryness under reduced pressure. The residue was dissolved in ethanol (40 ml.) and heated for 10 minutes at 60° C. The insoluble substance was separated out and the ethanolic layer was allowed to stand overnight at ambient temperature to give crystalline 3-(N-chloroacetyl-N-hydroxyamino)propylphosphonic acid (1.85 g.), mp: 163°-165° C. (dec.).

Provenance & Evidence