Acetone → HCID 20096454, compound

Participants

Reaction Steps

To a suspension of 4.5 g of sodium borohydride in 30 ml of water and 70 ml of tetrahydrofuran there are added dropwise with stirring and heating to 40°-50° C. in the course of half an hour a solution of 1.9 g of 6-chloro-7-carbomethoxybenzo-1,2,3-thiadiazole in 30 ml of tetrahydrofuran (dissolved under hot conditions). Heating of the mixture is continued until the reaction is complete, and the mixture is then cooled to -20° to -30° C. using a CO2 cooling bath and treated dropwise with 15 ml of acetone, during which process gas is evolved vigorously. The reaction mixture is subsequently brought to pH 3 using 15% hydrochloric acid, with further vigorous cooling at -20° to -10° C. (evolution of gas), and stirring is continued overnight. Most of the tetrahydrofuran is then evaporated on a rotary evaporator, and the residue is extracted using ethyl acetate. The extracts are washed with water, dried over sodium sulfate and evaporated. The residue gives the title compound of m.p. 138°-140° C.

Provenance & Evidence