ChemicalBook CAS DataBase List O-Diphenylphosphinylhydroxylamine

O-Diphenylphosphinylhydroxylamine synthesis

4synthesis methods

Product Name:O-Diphenylphosphinylhydroxylamine
CAS Number:72804-96-7
Molecular formula:C12H12NO2P
Molecular Weight:233.2

1499-21-4 Synthesis

1499-21-4
332 suppliers
$11.19/5G

72804-96-7
196 suppliers
$6.00/1g

Yield:72804-96-7 82%

Reaction Conditions:

with sodium hydroxide;hydroxylamine hydrochloride in 1,4-dioxane;water at 0 - 22; for 0.166667 h;

Steps:

B.1
A 5 L 4-neck round bottom flask (rbf) fitted with an overhead stirrer & a thermocouple was charged with; (1) a solution of NaOH (60.85 g, 1.52 mol, 2.4 eq) in 180 mL water, (2) a solution of hydroxylamine-HCl (110.12 g, 1.58 mol, 2.5 eq) in 180 mL water and (3) 180 mL dioxane. The mixture was cooled in an ice/acetone bath to to 0 °C. 150 g of ice was added, followed by a precooled (to about 10 °C) solution of diphenylphosphinic chloride (150.0 g, 0.634 mol, 1 eq) in 180 mL dioxane (added all at once). The reaction became very thick with a white precipitate, requiring vigorous stirring. The internal temperature rose to 22 ⁰C. After 5 additional minutes stirring (10 minutes maximum) , the reaction mixture was diluted with 2.5 L of ice cold water and filterered thru a large fritted funnel (15 cm diameter). The crude material was left on the frit to drain for one hour, then transfered back into the 5 L rbf. The solid was suspended in 500 mL ice cold 0.25N NaOH solution and vigorously stirred for five minutes (no more than 10 min), then filterered again, washing 2x with ice cold water and left to dry overnight on the fritted filter. The partially dried material was dried for 12 h in a vacuum oven (50 °C, 0.1 torr) and then well crushed with a mortar & pestal. An additional 16 h of drying in the vacuum oven afforded 122 g (82 %) the above compound as a white powder.

References:

BAYER PHARMACEUTICALS CORPORATION WO2007/64883, 2007, A2 Location in patent:Page/Page column 190

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2524-64-3 Synthesis