ethyl phosphonothioic dichloride, anhydrous → O,O-bis(6-fluoro-2-pyridinyl) ethylphosphonothioate

HRID 2049121

Reaktionsgleichung

Reaktionsgleichung von HRID 2049121
[Na].[F:2][C:3]1[N:8]=[C:7]([OH:9])[CH:6]=[CH:5][CH:4]=1.[CH2:10]([P:12](Cl)(Cl)=[S:13])[CH3:11]>Cl[Hg]Cl.C(#N)C>[CH2:10]([P:12](=[S:13])([O:9][C:7]1[CH:6]=[CH:5][CH:4]=[C:3]([F:2])[N:8]=1)[O:9][C:7]1[CH:6]=[CH:5][CH:4]=[C:3]([F:2])[N:8]=1)[CH3:11]

Komponenten

6

Edukt 3

HCID 61246ethyl phosphonothioic dichloride, anhydrousHCID 5360545SodiumHCID 178516046HCID 178516046, Verbindung

Produkt 1

HCID 54415562O,O-bis(6-fluoro-2-pyridinyl) ethylphosphonothioateAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24085Mercuric ChlorideKatalysatorHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

Into a 500 milliliter (ml) flask were placed 22 grams (g) (0.15 mole (m)) of the sodium salt of 6-fluoro-2-pyridinol, 1 gram HgCl2 and 200 milliliters of acetonitrile. The mixture was stirred while 9.5 grams (0.075 mole) of ethylphosphonothioic dichloride was added. An exotherm from 24° C. to 38° C. was obtained. The mixture was stirred at 40°-45° C. for five hours and allowed to cool. The insolubles were filtered off and the liquid phase distilled under reduced pressure until all the solvent was removed. The resulting oil was taken up in 300 milliliters of methylene chloride and washed once with 200 milliliters of water, once with 200 milliliters of aqueous 2% NaOH and twice with 200 milliliters portions of water. The product layer was dried over sodium sulfate, filtered and distilled under reduced pressure at 45° C. until the solvent was removed. The resulting oil was mixed in 150 mls of n-hexane and cooled to dry ice/acetone bath temperatures. The resulting solids were filtered off and dried to give a 60% yield of O,O-bis(6-fluoro-2-pyridinyl) ethylphosphonothioate, a solid, m.p. 47°-49° C. Product was confirmed by N.M.R. and I.R. spectra (compound No. 1).

Aufarbeitung

  1. customInto a 500 milliliter (ml) flask were placed
  2. additionwas added
  3. customAn exotherm from 24° C. to 38° C. was obtained
  4. temperatureto cool
  5. filtrationThe insolubles were filtered off
  6. distillationthe liquid phase distilled under reduced pressure until all the solvent
  7. customwas removed
  8. washwashed once with 200 milliliters of water, once with 200 milliliters of aqueous 2% NaOH and twice with 200 milliliters portions of water
  9. dry with materialThe product layer was dried over sodium sulfate
  10. filtrationfiltered
  11. distillationdistilled under reduced pressure at 45° C. until the solvent
  12. customwas removed
  13. additionThe resulting oil was mixed in 150 mls of n-hexane
  14. temperaturecooled to dry ice/acetone bath temperatures
  15. filtrationThe resulting solids were filtered off
  16. customdried

Quellen und Nachweise

ORD-Eintrag
ord-224df4d94be344e799c38e6f16a7ec76
Quelldatensatz
uspto-grants-1980_04
Patentnummer
US04196293

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