Acetone → HCID 20096454, compound

Participants

Reaction Steps

A solution of 1.9 g of 6-chloro-7-carbomethoxybenzo-1,2,3-thiadiazole in 30 ml of tetrahydrofuran (dissolved hot) is added dropwise to a suspension of 4.5 g of sodium borohydride in 30 ml of water and 70 ml of tetrahydrofuran in the course of half an hour, while stirring and heating at 40°-50° C. Heating is continued until the reaction is complete, the mixture is cooled to -20° to -30° C. with a CO2 cooling bath and 15 ml of acetone are added dropwise, vigorous evolution of gas being observed. The reaction mixture is then acidified to pH 3 with 15% hydrochloric acid at -20° C. to -10° C., with further vigorous cooling (evolution of gas), and stirring is continued overnight. The majority of the tetrahydrofuran is then stripped off on a rotary evaporator and the residue is extracted with ethyl acetate. The extracts are washed with water, dried over sodium sulfate and evaporated. The residue gives the title compound of melting point 138°-140° C.

Provenance & Evidence