4-(Dimethylamino)Benzaldehyde → 4-[4-(3-Chlorophenyl)-2,2-dimethyl-2,5-dihydro-1,3-oxazol-5-yl]-N,N-dimethylaniline

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Reaction Steps

3 g of 3-(m-chlorophenyl)-2,2-dimethyl-2H-azirine and 2.4 g of p-(dimethylamino)benzaldehyde were exposed to light for 2 hours in 350 ml of 1,4-dioxane (with the light source described in Example 2). After removing the solvent in a water-jet vacuum, the residue was chromatographed twice on aluminum oxide (neutral, activity 1), the elution was carried out in both cases with n-hexane/ether (9:1). Crystallization from n-hexane gave 4-(m-chlorophenyl)-5-[p-(dimethylamino)phenyl]-2,2-dimethyl-3-oxazoline which melted at 96°-97° C. after drying for 5 hours at 60° C. and 13 Torr.

Provenance & Evidence