Sodium Hydroxide → O-(Diphenylphosphinyl)hydroxylamine

HRID 469533Notes

Reaction equation

HRID 469533 reaction equation
Cl.[NH2:2][OH:3].[OH-].[Na+].[C:6]1([P:12](Cl)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:13])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>O.O1CCOCC1>[C:6]1([P:12]([O:3][NH2:2])([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:13])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 3

HCID 14798Sodium Hydroxide2×HCID 73910Diphenylphosphinic chlorideHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 10955453O-(Diphenylphosphinyl)hydroxylamineYield 59%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent3×HCID 312751,4-DioxaneSolvent2×

Procedure

To a stirred solution of hydroxylamine hydrochloride (9.5 g, 137 mmol) in H2O (21 mL) was added aqueous sodium hydroxide (4.6 g, 116 mmol) in H2O (16 mL), followed by dioxane (66 mL). The resulting solution was cooled in an ice/salt bath, and diphenylphosphinyl chloride (11.8 g, 50 mmol) in dioxane (50 mL) was added in one portion with vigorous stirring. Stirring was continued for 5 minutes as copious precipitation ensued. Water (200 mL) was added, and the slurry filtered, and was purified by stirring the slurry with aqueous sodium hydroxide (1 g, 25 mmol) in water (100 mL) at 0° C. for 30 min, followed by filtration and drying in vacuo to afford 6.8 g (59%) of the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 7.38-7.57 (m, 6H) 7.64-7.79 (m, 4H).

Workup

  1. temperatureThe resulting solution was cooled in an ice/salt bath
  2. customwas continued for 5 minutes as copious precipitation
  3. additionWater (200 mL) was added
  4. filtrationthe slurry filtered
  5. customwas purified
  6. filtrationfollowed by filtration
  7. customdrying in vacuo

Sources & evidence

ORD record
ord-22258e619ff54725aeb08cd0acbf6b3a
Source dataset
uspto-grants-2014_01
Patent number
US08629143B2

Reaction notes

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