Benzene → O,O-diethyl S-[alpha-(5-methyl-3-oxo-4-isoxazolin-2-yl)benzyl] phosphorodithioate

HRID 1706874Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1706874
Cl[CH:2]([N:9]1[C:13](=[O:14])[CH:12]=[C:11]([CH3:15])[O:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[P:16]([S-:24])([O:21][CH2:22][CH3:23])([O:18][CH2:19][CH3:20])=[S:17].[K+].C1C=CC=CC=1>CC(C)=O>[P:16]([S:24][CH:2]([N:9]1[C:13](=[O:14])[CH:12]=[C:11]([CH3:15])[O:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)(=[S:17])([O:21][CH2:22][CH3:23])[O:18][CH2:19][CH3:20]

Komponenten

5

Edukt 3

HCID 241BenzeneHCID 11481509Potassium diethyl dithiophosphateHCID 203329272-(alpha-Chlorobenzyl)-5-methyl-4-isoxazolin-3-one

Produkt 1

HCID 20332900O,O-diethyl S-[alpha-(5-methyl-3-oxo-4-isoxazolin-2-yl)benzyl] phosphorodithioateAusbeute 62,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

To a solution of 1.12 g of 2-(α-chlorobenzyl)-5-methyl-4-isoxazolin-3-one in 15 ml of acetone were added 1.12 g of potassium O,O-diethyl dithiophosphate, and the mixture was then shaken for several minutes. After this, 20 ml of benzene were added to the reaction mixture and then most of the acetone was distilled off. After filtering the solution, the solvent was distilled from the filtrate and the remaining yellowish-brown oil was purified by column chromatography through silica gel eluted with a 20:1 by volume mixture of benzene and acetone. There were obtained 1.16 g (62.0% of theory) of O,O-diethyl S-[α-(5-methyl-3-oxo-4-isoxazolin-2-yl)benzyl] phosphorodithioate, in the form of a pale yellow oil, n23D =1.5697.

Aufarbeitung

  1. distillationmost of the acetone was distilled off
  2. filtrationAfter filtering the solution
  3. distillationthe solvent was distilled from the filtrate
  4. customthe remaining yellowish-brown oil was purified by column chromatography through silica gel
  5. washeluted with a 20:1 by volume mixture of benzene and acetone

Quellen und Nachweise

ORD-Eintrag
ord-1a3983915c1941059db83f283768714a
Quelldatensatz
uspto-grants-1980_06
Patentnummer
US04209512

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