Ammonia → Dimethyl 3-benzyl-2-isoxazolin-5-ylphosphonate

HRID 1084797

Reaktionsgleichung

Reaktionsgleichung von HRID 1084797
C1(N=C=O)C=CC=CC=1.[CH:10]([P:12](=[O:17])([O:15][CH3:16])[O:13][CH3:14])=[CH2:11].[C:18]1([CH2:24][CH2:25][N+:26]([O-])=[O:27])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.N>C1(C)C=CC=CC=1.C(N(CC)CC)C>[CH2:24]([C:25]1[CH2:11][CH:10]([P:12](=[O:17])([O:15][CH3:16])[O:13][CH3:14])[O:27][N:26]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Komponenten

7

Edukt 4

HCID 222AmmoniaHCID 7672Phenyl isocyanateHCID 78376Dimethyl vinylphosphonateHCID 802081-Nitro-2-phenylethane

Produkt 1

HCID 20062388Dimethyl 3-benzyl-2-isoxazolin-5-ylphosphonate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittel2×HCID 8471TriethylamineLösungsmittel2×

Versuchsvorschrift

13.5 ml (0.124 mol) of phenyl isocyanate, 9.5 g (0.07 mol) of dimethyl vinylphosphonate and 1 ml of triethylamine are introduced into 120 ml of toluene. A solution of 9.3 g (0.062 mol) of 2-phenylnitroethane and 1 ml of triethylamine dissolved in 150 ml of toluene is added dropwise in 5 hours, the mixture is stirred overnight and then for 30 minutes after addition of 30 ml of concentrated aqueous ammonia, precipitated diphenylurea is removed by filtration and washed with ethyl acetate, and the combined organic phases are extracted by shaking successively with water, 2 N hydrochloric acid and water, and are dried and concentrated. 13.9 g of reddish brown oil remain.

Aufarbeitung

  1. additionis added dropwise in 5 hours
  2. customprecipitated diphenylurea
  3. customis removed by filtration
  4. washwashed with ethyl acetate
  5. extractionthe combined organic phases are extracted
  6. stirringby shaking successively with water, 2 N hydrochloric acid and water
  7. customare dried
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-64ce610377564b8b98bef1e464548e59
Quelldatensatz
uspto-grants-1991_04
Patentnummer
US05006515

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