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2-Methyl-N-(phenylmethylene)-2-propanamine → 2-(1,1-Dimethylethyl)-3-phenyloxaziridine

HRID 1884079
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1884079
[CH:1](=[N:8][C:9]([CH3:12])([CH3:11])[CH3:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)(O)[O-:14].[Na+].OOS([O-])=O.[K+].O1CN1>O.CC(C)=O>[C:9]([N:8]1[CH:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[O:14]1)([CH3:12])([CH3:11])[CH3:10]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 1112402-Methyl-N-(phenylmethylene)-2-propanamineHCID 516892Sodium BicarbonateHCID 15817734OxaziridineHCID 23707502Potassium hydroxy sulfite

Produkt 1

HCID 983712-(1,1-Dimethylethyl)-3-phenyloxaziridine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180
Acetone
Lösungsmittel
HCID 962WaterLösungsmittel2×

Versuchsvorschrift

13.2 gm (0.082 moles) of the N-benzylidene-t-butylamine prepared as in Example 1 was added to a 600 ml beaker containing 28.8 gm of sodium bicarbonate (0.3428 moles) in a solution consisting of 50 ml water and 50 ml acetone. The mixture was stirred vigorously with a mechanical paddle stirrer. While stirring, 60 gm (0.098 moles) of Oxone® was added portion wise over a 3 to 5 minute period. The resulting three-phase mixture was initially bluish in color and eventually faded to a pale yellow color as the reaction proceeded. The reaction was stirred at ambient temperature for one hour and followed by GC analysis as described in Example 1. The GC analysis revealed only a trace of the starting material (very tiny peak at 3.72 minutes) and predominant conversion to the oxaziridine, a peak having a retention time of 4.45 minutes. The mixture was diluted with 300 ml of water to dissolve any salts therein. The 2-phase mixture was extracted with 100 ml of hexane. The hexane layer was separated and concentrated under vacuum to remove all solvent. The resulting, almost clear liquid, 2-t-butyl-3-phenyl oxaziridine product weighed 13.74 gm (94.7% crude yield).

Aufarbeitung

  1. additionwas added to a 600 ml beaker
  2. stirringWhile stirring
  3. stirringThe reaction was stirred at ambient temperature for one hour
  4. customat 3.72 minutes
  5. dissolutionto dissolve any salts
  6. extractionThe 2-phase mixture was extracted with 100 ml of hexane
  7. customThe hexane layer was separated
  8. concentrationconcentrated under vacuum
  9. customto remove all solvent

Quellen und Nachweise

ORD-Eintrag
ord-53cd66ec731043dbbd35f926ef6ca11a
Quelldatensatz
uspto-grants-2004_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06762322B1

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