Diphenylphosphinic chloride → O-(Diphenylphosphinyl)hydroxylamine

Temperature

0 °C

To a suspension of hydroxylamine hydrochloride (29.4 g) in dichloromethane (200 mL) was added diisopropylethylamine (54.6 g) over 3 minutes in a methanol-ice bath under a nitrogen atmosphere. A white precipitate was formed upon the addition. After stirring for 1 hour under the bath, a solution of diphenylphosphinic chloride (20.0 g) in dichloromethane (20 mL) was added over 60 minutes. A white crystal was formed upon the addition. The mixture was warmed to 0° C. over 1 hour with stirring. The reaction was quenched by adding water (200 mL) over 3 minutes. After stirring the mixture for 0.5 hour, the crystal was collected by filtration. The crystal was washed with water (50×3 mL) followed by diisopropyl ether (50×3 mL). The collected crystal was dried overnight in the air and 3 hours under a reduced pressure with slight warming (4° C.) to give a crude product. The crude product was triturated in EtOH (ethanol) to give (aminooxy)(diphenyl)phosphine oxide as a white crystal (15.3 g).

1. customA white precipitate was formed upon the addition
2. customA white crystal was formed upon the addition
3. stirringwith stirring
4. customThe reaction was quenched
5. additionby adding water (200 mL) over 3 minutes
6. stirringAfter stirring the mixture for 0.5 hour
7. filtrationthe crystal was collected by filtration
8. washThe crystal was washed with water (50×3 mL)
9. customThe collected crystal was dried overnight in the air and 3 hours under a reduced pressure
10. temperaturewith slight warming (4° C.)
11. customto give a crude product
12. customThe crude product was triturated in EtOH (ethanol)

ORD record

ord-80161415dc3d4f128536e89db425e061

Source dataset

uspto-grants-2006_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07153854B2