Sodium Azide → P,P-Diphenylphosphinic azide

HRID 1703433Notes

Reaction equation

HRID 1703433 reaction equation
[C:1]1([P:7](Cl)([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N-:16]=[N+:17]=[N-:18].[Na+]>CC(C)=O>[P:7]([N:16]=[N+:17]=[N-:18])([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[O:8]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 73910Diphenylphosphinic chloride

Product 1

HCID 199401P,P-Diphenylphosphinic azide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Following the procedure of Baldwin and Washburn, J. Org. Chem., 30, 3860 (1965), 6.99 g (0.0297 mole) of diphenylphosphinyl chloride and 2.09 g (0.032 mole) of sodium azide were stirred in 40 ml of anhydrous acetone under a nitrogen atmosphere for 48 hours. The sodium chloride and unreacted sodium azide was removed by gravity filtration and the acetone solvent removed in vacuo. The crude diphenylphosphinic azide was analyzed for Cl content and in all cases only trace quantities (less than .1%) were found. The colorless diphenylphosphinic azide was purified by distillation to yield 6.31 g (87%) boiling at 138°-140° C./0.05 mm; literature value 137°-140° C./0.05 mm.

Workup

  1. customThe sodium chloride and unreacted sodium azide was removed by gravity filtration
  2. customthe acetone solvent removed in vacuo
  3. distillationThe colorless diphenylphosphinic azide was purified by distillation
  4. customto yield 6.31 g (87%) boiling at 138°-140° C./0.05 mm
  5. customliterature value 137°-140° C./0.05 mm

Sources & evidence

ORD record
ord-44997d8410d24fd6acc8154dc5e967d4
Source dataset
uspto-grants-1978_11
Patent number
US04124356

Reaction notes

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