Phosphorus pentachloride → HCID 13037527, compound

HRID 2058925Notes

Reaction equation

HRID 2058925 reaction equation
[CH2:1]([O:3][C:4](=[O:19])[NH:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[P:13](OCC)([CH3:15])=[O:14])[CH3:2].P(Cl)(Cl)(Cl)(Cl)Cl>C(Cl)(Cl)(Cl)Cl>[CH3:15][P:13]1(=[O:14])[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH2:6][N:5]1[C:4]([O:3][CH2:1][CH3:2])=[O:19]

Participants

4

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 70542392HCID 70542392, compound

Product 1

HCID 13037527HCID 13037527, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

Under anhydrous conditions, a mixture of 2-[P-ethoxy-P-methylphosphinyl]benzyl carbamic acid ethyl ester (1.2 g, 0.0025 mol) and phosphorus pentachloride (0.52 g, 0.0025 mol) in 10 ml. of carbon tetrachloride was heated at reflux for 1.5 hours. The reaction mixture was concentrated in vacuo and the resulting residue was dissolved in methylene chloride. The methylene chloride solution was washed with ice water, dried over magnesium sulfate and concentrated to produce a yellow oil. Distillation of this yellow oil at 150° C. and 0.5 torr produced an oil which solidified to yield 1-methyl-2-ethoxycarbonyl-2,3-dihydro-1H-2,1-benzazaphosphole-1-oxide as a white powder having a melting point of 102°-104° C. and the following analysis:

Workup

  1. temperatureat reflux for 1.5 hours
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. dissolutionthe resulting residue was dissolved in methylene chloride
  4. washThe methylene chloride solution was washed with ice water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customto produce a yellow oil
  8. distillationDistillation of this yellow oil at 150° C.
  9. custom0.5 torr produced an oil which

Sources & evidence

ORD record
ord-8910b257fb5a4eae8f39f4d3381d5b83
Source dataset
uspto-grants-1982_03
Patent number
US04319913

Reaction notes

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