p-Aminoacetophenone → N-(p-acetylphenyl)acetamide

Participants

Reaction Steps

To 250 ml of KOH dried pyridine was added 50 g (0.37 mole) of p-aminoacetophenone and 39.6 g of acetic anhydride. After one and a half hours of stirring at room temperature, the solution had become a thick suspension of a white solid. Filtration and drying gave 44 g of p-acetamidoacetophenone. This solid (44 g, 0.25 mole) was then suspended in 500 ml methylene chloride and treated with 44 g Br2 (0.275 mole). The reaction was allowed to proceed overnight whereupon it was stripped and dried under high vacuum, then suspended in 200 ml absolute EtOH and treated with 60 g 2-amino-2-thiazoline (0.59 mole). The reaction was stirred for 2 days then stripped, taken up in water and extracted with methylene chloride. The organic phase was washed with water, brine and was dried with sodium sulfate. Flash column chromatography with 2% MeOH/98% CH2Cl2 gave 10.2 g (0.039 mole) of the Formula (III) compound, 6-acetamidophenyl-2,3-dihydroimidazo[2,1-b]thiazole.

Provenance & Evidence