Pivalaldehyde → N-(1-(1H-1,2,3-benzotriazol-1-yl)-2,2-dimethylpropyl)-4-methylbenzamide

Participants

Reaction Steps

A suspension of p-toluamide (4.11 g, 30.4 mmol), pivaldehyde (2.62 g, 30.4 mmol), and benzotriazole (3.62 g, 30.4 mmol) in toluene (200 mL) were treated with p-toluenesulfonic acid (286 mg, 1.52 mmol). The solution was heated at reflux under Dean-Stark conditions for 10 hours, cooled gradually to ambient temperature, and further cooled at 5° C. The white precipitate which formed was collected by filtration and was washed with 50% ether/hexanes (100 mL) to provide 6.67 g of the desired product as a white solid.

Provenance & Evidence