Reaction #61840

Reaction equation

1-(α-Bromoacetyl)naphthalene

1,1-dimethylurea

ethyl acetate

→

title compound

2-dimethylamino-4-(naphth-1-yl)oxazole

Solvents

dimethylformamide

Conditions

Workup

1. 1
   TemperatureThe mixture was cooled
2. 2
   Washwashed with sodium bicarbonate solution, water, brine
3. 3
   Dryingdried with sodium sulphate
4. 4
   Filtrationfiltered
5. 5
   Otherevaporated in vacuo

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.

Source