Dimethyl Sulfoxide → HCID 136026269, compound

Participants

Reaction Steps

To 50 mL of methyl sulfoxide were added in sequence 2.2 g (6.2 mmol ) of 2-propionyl-3-hydroxy-5-(N-(2-propynyl)-3-oxo-(2H)-1,4-benzoxazin-6-yl)cyclohex-2-en-1-one, 0.70 g (7.4 mmol) of ethoxyamine hydrochloride and 0.60 g (7.3 mmol) of anhydrous sodium acetate. The resulting mixture was stirred at ambient temperature for 3.5 hours. The reaction mixture was then diluted with 400 mL of 0.2N HCl and extracted four times with 20 mL portions of dichloromethane. The extracts were combined, washed with aqueous NaCl, dried over MgSO4 and filtered through a short pad of silica gel. Evaporation off of the solvent gave the crude product as a light yellow glass, which solidified upon standing. The solid was triturated in ether and the product isolated by filtration which afforded the above-named product as a white solid which melted at 100°-102° C. in a yield of 1.3 g (53 percent of theoretical). 1H NMR (CDCl3): d1.08-1.47 (m, 6H, both --CH2CH3 's), 2.31 (t, J=2 Hz, 1H,--C--CH), 2.62-3.64 (m, 7H), 4.17 (q, J=7 Hz, 2H, OCH2CH3), 4.67 (s, 2H, --OCH2C=O), 4.74(d, J=2 Hz, 2H,--NCH2), 6.87-7.12 (m, 3H, aromatic H's), 15.10 (broad s, 1H, enol H); (Compound 11).

Provenance & Evidence