Diphenylphosphinic chloride → P,P-Diphenylphosphinic azide

HRID 1863199Notes

Reaction equation

HRID 1863199 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.C[Si]([N:20]=[N+:21]=[N-:22])(C)C>>[C:1]1([P:7]([N:20]=[N+:21]=[N-:22])([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

Participants

3

Reactant 2

HCID 73910Diphenylphosphinic chlorideHCID 78378Azidotrimethylsilane

Product 1

HCID 199401P,P-Diphenylphosphinic azide

Conditions

Temperature
60 °C

Procedure

Following a previously [Paciorek et al, Inorg. Nucl. Chem. Letters, 2, 39 (1966)] developed procedure, diphenylphosphinyl chloride (14.87 g, 62.86 mmol) was introduced into a tube (in the inert atmosphere enclosure). Trimethylsilyl azide (10.45 g, 90.69 mmol) was then condensed onto this material on a vacuum line at liquid nitrogen temperature. The tube was sealed in vacuo and heated at 60° C. for 48 hr. Thereafter, it was cooled, opened to a vacuum system and the volatiles were collected in a liquid nitrogen trap (originally without pumping at room temperature, finally with pumping at 70° C.). The total time required to remove the volatiles (excess (CH3)3SiN3 and the by-product (CH3)3SiCl) was 16 hr. A quantitative yield of pure diphenylphosphinyl azide was realized.

Workup

  1. additionwas introduced into a tube (in the inert atmosphere enclosure)
  2. customcondensed onto this material on a vacuum line at liquid nitrogen temperature
  3. customThe tube was sealed in vacuo
  4. temperatureThereafter, it was cooled
  5. customthe volatiles were collected in a liquid nitrogen trap (originally
  6. customwithout pumping at room temperature
  7. customwith pumping at 70° C.
  8. customto remove the volatiles (excess (CH3)3SiN3

Sources & evidence

ORD record
ord-72b18d3b314a4b59a5da9634f484da20
Source dataset
uspto-grants-1979_09
Patent number
US04168287

Reaction notes

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