2-(4-acetylphenyl)acetonitrile

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred solution of 6.36 g. (0.04 mole) of p-acetylphenyl acetonitrile in 100 ml. of methylene chloride is added 6.40 g. (0.04 mole) of bromine in 50 ml. of methylene chloride. The reaction solution is warmed for a few minutes and the heat then removed. After a few minutes the bromine color disappears. The reaction mixture is stirred an additional 1/2 hour at room temperature. The methylene chloride is removed in vacuo on a rotary evaporator. To the residue is added 100 ml. of ethanol and 4.73 g. (0.04 mole) of amidinothiourea. The reaction mixture is heated with stirring for 1 hour under reflux, cooled in ice and then filtered. There is obtained 7.6 g. of product, m.p. 242°-246° (dec.). Recrystallization is from ethanol to which is then added enough water to form a solution. Ether is added to the cloudy point. There is obtained 5.9 g. of crystals, m.p. 259°-261° (dec.). The reaction solution is warmed for a few minutes the heat then removed After a few minutes the bromine color disappears The methylene chloride is removed in vacuo on a rotary evaporator To the residue is added 100 ml The reaction mixture is heated with stirring for 1 hour under reflux cooled in ice filtered There is obtained 7.6 g Recrystallization is then added enough water to form a solution There is obtained 5.9 g