Acetylacetone → HCID 12296897, compound

Participants

Reaction Steps

2,4,6-trimethylpyrimidine dihydrate (0.79 g, 5.0 mmole, prepared from acetylacetone and acetamidine hydrochloride according to A. Bowman, J. Chem. Soc. 1937;494-495) in dichloromethane (10 mL) was dried over Na2SO4 and filtered. Separately, O-(mesitylenesulfonyl)hydroxylamine containing ca. 25% water (1.57 g, ca. 5.4 mmole) was dissolved in dichloromethane (10 mL) and dried over Na2SO4 and filtered. The dry O-(mesitylenesulfonyl)hydroxylamine filtrate was added dropwise to the dry 2,4,6-trimethylpyrimidine filtrate at 0 C. Stirring was continued 5 hr at 0 C. and then 16 hr at 4 C. The reaction mixture was concentrated at reduced pressure to ca. 10 mL and treated with ca. 3 mL ether to cause separation of a white powder, which was filtered, washed with 10 mL 1:1 dichloromethane/ether, and dried to yield 1.27 of crude product in two crops. Recrystallization from methanol/dichloromethane/ether gave 1.18 g of the title compound, mp 183-185 C.

Provenance & Evidence