Potassium Carbonate → Salithion

HRID 371695Notes

Reaction equation

HRID 371695 reaction equation
[C:1](=[O:4])([O-])[O-].[K+].[K+].Cl[P:8]1(=[S:18])[O:13][CH2:12][C:11]2[CH:14]=[CH:15][CH:16]=[CH:17][C:10]=2[O:9]1>CO>[CH3:12][O:13][P:8]1(=[S:18])[O:4][CH2:1][C:11]2[CH:14]=[CH:15][CH:16]=[CH:17][C:10]=2[O:9]1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 143466792-Chloro-2H,4H-1,3,2lambda~5~-benzodioxaphosphinine-2-thione

Product 1

HCID 19657SalithionYield 92%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Into a reaction flask was placed 150 ml methanol, 21 g (0.15 moles) potassium carbonate, and 22 g (0.1 moles) of 2-chloro-4H-1,3,2-benzodioxaphosphorin-2-sulfide. The reaction mixture was stirred at room temperature for 2 hours, filtered, and the axcess methanol recovered via reduced pressure. The residue was dissolved in 50 ml chloroform, washed with two portions of water (total of 100 ml), dried over sodium sulfate, filtered, and the solvent removed under reduced pressure. The residue crystallized to yield 19.2 g (92%) of 2-methoxy-4H-1,3,2-benzodioxaphosphorin-2-sulfide having a melting point 50°-53° C. The melting point, IR and NMR spectra of this product were identical to the known insecticide, Salithion. By using corresponding alkanols instead of methanol, the corresponding 2-alkoxy derivatives are obtained.

Workup

  1. customInto a reaction flask was placed
  2. filtrationfiltered
  3. customthe axcess methanol recovered via reduced pressure
  4. dissolutionThe residue was dissolved in 50 ml chloroform
  5. washwashed with two portions of water (total of 100 ml)
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customthe solvent removed under reduced pressure
  9. customThe residue crystallized

Sources & evidence

ORD record
ord-6bf3cd655cf6451b9afbbb9193dcc6e9
Source dataset
uspto-grants-1978_05
Patent number
US04087490

Reaction notes

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