Acetyl chloride → Acetamide, N-(2,4,6-trimethylphenyl)-

Participants

Reaction Steps

A solution of 2,4,6-trimethyl-phenylamine (1) (50 g, 0.370 moles) in CH2Cl2 (500 mL) was cooled to 0° C. (ice-water bath). To this was added acetyl chloride (29.8 g, 27 mL, 380 mmol) during 5 minutes via an addition funnel; this was followed by portion-wise addition of Et3N (38.5 g, 53 mL, 380 mmol). The ice-bath was removed and the solution was allowed to warm to room temperature and stir for 2 h. The resultant ivory colored solid was collected by filtration and dried in vacuo. To remove residual Et3N.HCl, the solid was suspended H2O (600 mL) stirred for 0.5 h, collected by filtration and dried to a constant weight. The original organic filtrate was washed with H2O (3×100 mL) and brine (1×100 mL), dried (MgSO4), filtered and concentrated providing additional product. Combined with material collected from the water afforded 60.2 g (99% yield) of the desired acetamide. RP-HPLC Method: 2-100 B in 2 minutes.

Provenance & Evidence