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

Participants

Reaction Steps

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).

Provenance & Evidence