Sodium Hydroxide → O-(Diphenylphosphinyl)hydroxylamine

HRID 229616Notes

Reaction equation

HRID 229616 reaction equation
Cl.[NH2:2][OH:3].[OH-].[Na+].Cl[P:7](=[O:20])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>O.O1CCOCC1>[NH2:2][O:3][P:7](=[O:20])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 73910Diphenylphosphinic chlorideHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 10955453O-(Diphenylphosphinyl)hydroxylamineYield 36%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent2×

Procedure

To hydroxylamine hydrochloride (15.86 g, 228.2 mmol) in H2O (35 mL) cooled in an ice-salt bath was added 7.1 N NaOH (27.4 mL, 194.4 mmol) followed by 1,4-dioxane (100 mL). The solution was vigorously stirred for 15 min and then chlorodiphenylphosphine oxide (20.00 g, 84.52 mmol) was added as a solution in 1,4-dioxane (100 mL). The solution was stirred an additional 15 min as a white precipitate formed which was filtered. The solid was suspended in 0.25 N NaOH (250 mL) while stirring in an ice-salt bath for 1 h. The solid was then collected, washed with H2O (100 mL), and thoroughly dried under vacuum to afford 7.09 g of the above compound as a white powder (30.4 mmol, yield 36%). 1H-NMR (DMSO-d6) δ 7.72 to 7.67 (m, 4H), 7.50 to 7.40 (m, 6H); −P-NMR (DMSO-d6) δ 23.11 (br s, 1P).

Workup

  1. stirringThe solution was stirred an additional 15 min as a white precipitate
  2. customformed which
  3. filtrationwas filtered
  4. stirringwhile stirring in an ice-salt bath for 1 h
  5. customThe solid was then collected
  6. washwashed with H2O (100 mL)
  7. customthoroughly dried under vacuum

Sources & evidence

ORD record
ord-84a918f334d34617b6dc37ebe7dd5dc7
Source dataset
uspto-grants-2009_07
Patent number
US07563791B2

Reaction notes

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