Triethyl phosphite → Diethyl ((phenylthio)methyl)phosphonate

HRID 2050177Notes

Reaction equation

HRID 2050177 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-9bf45d92413a40589a2e62ed47b08b53
Source dataset
uspto-grants-1980_04
Patent number
US04200644

Reaction notes

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