Ethanol → HCID 86759071, compound

Participants

Reaction Conditions

Reaction Steps

7.0 g (26 mmol) of diethylthioxanthen-9-one are dissolved in 15 ml of hot ethanol and 15 ml of pyridine. Then hydroxylammonium chloride (3.6 g, 52 mmol) is added, and the reaction solution is stirred at 115° C. for 21 h. After cooling, water is added. The crude product is extracted with ethyl acetate, washed with water, dried over MgSO4, and concentrated. The residue is purified by column chromatography on silica gel with ethyl acetate-hexane (1:30 to 1:10) as an eluent. The product (an isomeric mixture) is obtained as a slightly yellow solid. 1H NMR (CDCl3), δ[ppm]: 1.23-1.32 (m, 6H), 2.65-2.72 (m, 2H), 2.77-2.86 (m, 2H), 7.12(s, 1H), 7.30-7.36 (m, 2H), 7.45 (dd, 1/2H), 7.53-7.55 (m, 1H), 7.80 (dd, 1/2H), 8.03 Cd, 1/2H), 8.09-8.48 (bs, 1H), 8.34 (dd, 1/2H), wherein 1/2H means 1H of either isomer.

Provenance & Evidence