Thionyl Chloride → Oxazole, 4,5-dihydro-4,4-dimethyl-2-phenyl-, hydrochloride

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Reaction Steps

To 40 ml of freshly distilled thionyl chloride at 0° was added in portions over 15 minutes with stirring 3.86 g (0.02 mol) 2-benzoylamino-2-methyl-1-propanol. The solution was warmed to room temperature and heated under reflux for 2 hours. The thionyl chloride was removed under reduced pressure to afford a yellow oil which crystallized at 0° following the addition of anhydrous ether. The solid was triturated in anhydrous ether overnight and isolated by filtration under a nitrogen atmosphere. After drying in vacuo over calcium sulfate, 2.00 g (0.009 mol), 45%, 2-phenyl-4,4-dimethyl-1,3-oxazoline hydrochloride was obtained as a white solid, mp 149°-151°; ir (KBr) 1640 (c=N) cm-1, pmr (D2O) δ 1.60 (s, 6H), 4.70 (s, 2H) and 7.3-8.2 (m, 5H) ppm.

Provenance & Evidence