Tetrahydrofuran → HCID 20339459, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 3-chloro-2,6-diaminopyridine (129 g. 0.9 mole) in 1000 ml. of tetrahydrofuran and 250 ml. of water containing sodium bicarbonate (84 g., 1.0 mole) is stirred at 0° C. while adding ethyl chloroformate (114 g. 1.05 mole) dropwise over 1/2 hour. The mixture is stirred at 0° C. over night. The dark solution is filtered through activated carbon and the organic layer of the filtrate is separated, dried and concentrated in vacuo. The residual oil is taken up in ether, washed with 5 N sodium hydroxide and with saturated sodium chloride solution, dried and concentrated in vacuo. A light amber oil (162 g.) which solidifies when triturated in petroleum ether is obtained. The solid is purified by extracting into boiling hexane (10×300 ml) and cooling the extracts to give 131.6 g. of white solid, m.p. 66°-70°.

Provenance & Evidence