Triethyl phosphite → Diethyl ((phenylthio)methyl)phosphonate

HRID 2058143Notes

Reaction equation

HRID 2058143 reaction equation
[C:1]1([S:7][CH2:8]Cl)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:10]([O:12][P:13]([O:17]CC)[O:14][CH2:15][CH3:16])[CH3:11]>>[C:1]1([S:7][CH2:8][P:13](=[O:17])([O:14][CH2:15][CH3:16])[O:12][CH2:10][CH3:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 31215Triethyl phosphiteHCID 81623Chloromethyl phenyl sulphide

Product 1

HCID 99227Diethyl ((phenylthio)methyl)phosphonateYield 93.9%

Procedure

A stirred solution of 40.0 grams (0.25 mole) of phenylthiomethyl chloride and 58.2 grams (0.35 mole) of triethylphosphite was heated at 150°-160° C. for 4 hours, cooled and excess triethylphosphite removed by evaporation under reduced pressure. The residue was purified by distillation to give 61.1 grams (93.1%) of diethyl phenylthiomethylphosphonate; b.p. 155° C./0.6 mm. The nmr and the ir spectra were consistent with the assigned structure.

Workup

  1. temperaturecooled
  2. customexcess triethylphosphite removed by evaporation under reduced pressure
  3. distillationThe residue was purified by distillation

Sources & evidence

ORD record
ord-94e68297113243649b58753430e549ed
Source dataset
uspto-grants-1980_07
Patent number
US04215069

Reaction notes

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