Dimethyl Sulfoxide → HCID 136040515, compound

Participants

Reaction Steps

To 20 mL of methyl sulfoxide were added in sequence, 1.0 g (3.0 mmol) of 2-propionyl-3-hydroxy-5-(N-methyl-3-oxo-(2H)-1,4-benzoxazin-6-yl)cyclohex-2-en-1-one, 0.37 g (3.9 mmol) of ethoxyamine hydrochloride and 0.32 g (3.9 mmol) of anhydrous sodium acetate. The resulting mixture was stirred at ambient temperature for 5 hours, becoming a clear amber solution. The reaction mixture was diluted with 100 mL of water and extracted twice with 30 mL portions of ether. The extracts were combined, washed with water, then aqueous sodium chloride and dried over MgSO4 and filtered. Evaporation off of the solvent gave the crude product as an oily residue which solidified upon standing. The crude solid was crushed and triturated in ether. The purified above-named product, as a tan solid, was recovered in a yield of 0.9 g (80 percent of theoretical). The title compound melted at 90°-92° C.; 1H NMR(CDCl3): d1.05-1.48 (m, 6H, both --CCH2CH3 's), 2.55-3.62 (m including s at 3.31 for --N--CH3, 1 OH) 4.18 (q, J=7 Hz, 2H,--OCH2CH3), 4.60 (s, 2H, --OCH2C=O), 6.82-7.13 (m, 3H, aromatic H's), 15.10 (broad s, 1H, enol H); (Compound 3).

Provenance & Evidence