Diethyl chlorophosphate → Diethyl [[(diethylamino)sulfonyl]methyl]-phosphonate

HRID 1032661

Reaktionsgleichung

Reaktionsgleichung von HRID 1032661
[CH2:1]([N:3]([CH2:8][CH3:9])[S:4]([CH3:7])(=[O:6])=[O:5])[CH3:2].C([Li])CCC.[P:15](Cl)([O:20][CH2:21][CH3:22])([O:17][CH2:18][CH3:19])=[O:16]>O1CCCC1.CCCCCC>[CH2:1]([N:3]([CH2:8][CH3:9])[S:4]([CH2:7][P:15](=[O:16])([O:20][CH2:21][CH3:22])[O:17][CH2:18][CH3:19])(=[O:6])=[O:5])[CH3:2]

Komponenten

6

Edukt 3

HCID 13139Diethyl chlorophosphateHCID 75411N,N-DiethylmethanesulphonamideHCID 178418339Butyllithium

Produkt 1

HCID 54450901Diethyl [[(diethylamino)sulfonyl]methyl]-phosphonate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8058HexaneLösungsmittel

Versuchsvorschrift

A solution of N,N diethyl methanesulfonamide (4.7 g) in tetrahydrofuran (50 ml) was stirred at 20° C and treated with butyllithium in hexane (2.6 N, 27.9 ml) and diethyl chlorophosphate (5.2 ml). The cooling bath was removed and the mixture was stirred for 1.5 hours and poured onto ice. The resulting mixture was saturated with sodium bicarbonate, extracted with methylene chloride and the organic phase was washed with water, dried with sodium sulfate and magnesium sulfate, filtered and concentrated in vacuo to give diethyl [[(diethylamino)sulfonyl]methyl]-phosphonate.

Aufarbeitung

  1. customThe cooling bath was removed
  2. additionpoured onto ice
  3. extractionextracted with methylene chloride
  4. washthe organic phase was washed with water
  5. dry with materialdried with sodium sulfate and magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-71f608b9bd8e4b1fa222a5439dd487ac
Quelldatensatz
uspto-grants-1990_09
Patentnummer
US04959360

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