Dimethyl Sulfoxide → HCID 18999056, compound

Participants

Reaction Conditions

Reaction Steps

Anhydrous dimethylsulphoxide (1.2 ml) in anhydrous dichloromethane (20 ml) was added dropwise to a stirred, cooled (-75° C.) solution of oxalyl chloride (0.7 ml) in anhydrous dichloromethane (100 ml) under a nitrogen atmosphere. After 5 minutes a solution of (2-nitrophenyl)-(5-bromo-2-methoxypyridin-4-yl)methanol (2.5 g) in anhydrous dichloromethane (70 ml) was added dropwise keeping the temperature of the reaction mixture below -72° C. After a further 15 minutes triethylamine (5.3 ml) was added dropwise and the reaction mixture stirred at -75° C. for 10 minutes then the cooling bath was removed and the mixture allowed to warm to room temperature. Water (50 ml) was added, the organic layer separated, washed with water then dried (sodium sulphate) and evaporated to dryness. The product was dissolved in dichloromethane, treated with activated charcoal, filtered, evaporated to dryness, then recrystallised from dichloromethane/petroleum ether (60-80) to afford the title compound as a pale yellow solid (2.4 g). mp 128°-131° C. Rf =0.9 in 10% diethyl ether/dichloromethane on silica plates; 1 H NMR (360 MHz, CDCl3) δ 3.91 (3H, s), 6.69 (1H, s), 7.59 (1H, dd, J=1.5 and 7 Hz), 7.74 (1H, dt, J=1.5 and 7 Hz), 7.79 (1H, ddd, J=1.5 and 7 Hz), 8.13 (1H, dd, J=1.5 and 7 Hz), 8.38 (1H, s); IR (KBr) 1705 and 1695 cm-1.

Provenance & Evidence