Diphenylphosphinic chloride → O-(Diphenylphosphinyl)hydroxylamine

HRID 1487928Notes

Reaction equation

HRID 1487928 reaction equation
Cl.[NH2:2][OH:3].C(=O)(O)[O-].[Na+].[C:9]1([P:15](Cl)([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:16])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>O.O1CCOCC1.O1CCOCC1>[NH2:2][O:3][P:15](=[O:16])([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 3

HCID 73910Diphenylphosphinic chlorideHCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 10955453O-(Diphenylphosphinyl)hydroxylamineYield 49.6%

Reagents, catalysts & solvents 2

HCID 312751,4-DioxaneSolventHCID 218864351,4-Dioxane--water (1/1)Solvent

Conditions

Temperature
2.5 °C

Procedure

Into a 500-mL three neck round-bottom flask, was placed a solution of hydroxylamine hydrochloride (30.0 g, 432 mmol) in H2O/dioxane (90/45 mL). The solution was cooled to 0-5° C., then sodium bicarbonate (36.5 g, 434 mmol) was added portion-wise over 10 min and the mixture was stirred at 0-5° C. for 30 min. A solution of diphenylphosphinoyl chloride (41.0 g, 173 mmol) in dioxane (45 mL) was added drop-wise at 0-5° C. over 30 min, then the resulting mixture was stirred for an additional 2 h at ambient temperature. The resulting solids were collected by filtration and washed with water (200 mL), NaOH (0.25 M, 200 mL) and PE (200 mL). The product was dried to yield the title compound as a white solid (20 g, crude).

Workup

  1. stirringthe resulting mixture was stirred for an additional 2 h at ambient temperature
  2. filtrationThe resulting solids were collected by filtration
  3. washwashed with water (200 mL), NaOH (0.25 M, 200 mL) and PE (200 mL)
  4. customThe product was dried

Sources & evidence

ORD record
ord-812142c8ee7940e78e4f6d2daef391c2
Source dataset
uspto-grants-2016_08
Patent number
US09428502B2

Reaction notes

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