Acetamide → N-(2-methyl-5-nitrobenzyl)acetamide

Participants

Reaction Steps

To a solution of p-nitrotoluene (0.85 g; 0.05 mol) and para-formaldehyde (1.6 g; 0.05 mol) in concentrated sulfuric acid is added acetamide (8.85 g; 0.15 mol) in increments. This solution is stirred at room temperature for 18 hours. The reaction mixture is then poured onto ice. A precipitate is obtainined which is removed by filtration. This solid material is then mixed with butyl acetate, heated, and filtered while hot to remove insolubles. After cooling, 7.8 g (i.e., 75% yield) of product crystallizes out of solution. The product has the following characteristics: melting point of 141° to 143° C.; i.r. 3275, 1640 and 1660 cm-1 (sh); mass. spec. m/e 208.

Provenance & Evidence