Ethyl Acetate → 2-Dimethylamino-4-(naphth-1-yl)oxazole

Reaction equation

Br[CH2:2][C:3]([C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7][CH:6]=1)=O.[CH3:15][N:16]([CH3:20])[C:17]([NH2:19])=[O:18].C(OCC)(=O)C>CN(C)C=O>[CH3:15][N:16]([CH3:20])[C:17]1[O:18][CH:2]=[C:3]([C:5]2[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH:8]=[CH:7][CH:6]=2)[N:19]=1

Participants

Procedure

1-(α-Bromoacetyl)naphthalene (5 g) and 1,1-dimethylurea (6 g) were stirred in anhydrous dimethylformamide (20 ml) at 105° C. overnight. The mixture was cooled, added to ethyl acetate, washed with sodium bicarbonate solution, water, brine, dried with sodium sulphate, filtered and evaporated in vacuo. The title compound was obtained (0.60 g; m.p. 30-32° C.) following silica gel column chromatography of the residue in dichloromethane.