Oxalyl chloride → 4H-3,1-Benzoxazin-4-one, 2,2'-(2-phenylethenylidene)bis-

Participants

Reaction Steps

The Compound 11 (4 g, 9.28 mmol) was suspended in dry benzene (100 ml) and oxalyl chloride (3.2 ml, 37.18 mmol) was added dropwise under ice cooling. Then, with addition cf 8 drops of dry DMF, the mixture was stirred at room temperature for 2 hours. After the reaction, the solvent was removed and the residue was extracted with chloroform. The organic layer was washed with 1N.HCl, saturated brine, 4% NaHCO3 aqueous solution, and saturated brine and dried over magnesium sulfate. The solvent was evaporated. The residue was dissolved in chlcroform and applied on silica gel column for chromatography (benzene ethyl acetate=4:1). Recrystallization from isopropyl ether gave the desired compound 52 in crystal (3.26 g, yield, 89%). m.p., IR, and NMR pectra of the product fully agreed with those of the one obtained in Example 19.

Provenance & Evidence