Chloroacetyl chloride → HCID 20093932, compound

Participants

Reaction Conditions

Reaction Steps

7. A solution of 8.25 ml of chloroacetyl chloride in 25 ml of diethyl ether is added dropwise at 0° C. within 15 min. to a solution of 11.5 g of 3-methyl-2-(1H-2-imidazolyl)aniline in 0.35 l of tetrahydrofuran and 21 ml of pyridine. The reaction mixture is stirred at 0° C. for 1 h, and then poured into saturated aqueous sodium hydrogen carbonate solution. The mixture is extracted three times with chloroform. The organic extracts are evaporated in a vacuum. The residue (13 g) is dissolved in 300 ml of dioxan and treated with 200 ml of 1N aqueous sodium hydroxide solution. The mixture is stirred at room temperature for 16 h., then adjusted to pH 6 with hydrochloric acid and evaporated in a vacuum. The residue is suspended in absolute ethanol and the insoluble inorganic salt is filtered off. The filtrate is evaporated in a vacuum, the residue is dissolved in trifluoroacetic acid and stirred at room temperature for 16 h. The reaction mixture is evaporated in a vacuum and the residue is partitioned between chloroform and saturated aqueous sodium hydrogen carbonate solution. The organic phases are evaporated in a vacuum. The residue is chromatographed over a column of 500 g of silica gel. Elution with ethyl acetate gives in succession 1.4g of 10-methylimidazo[1,2-c]quinazolin-5(6H)-one (m.p. 308°-310° C.) and 9.0 g 11-methyl-5H-imidazo[1,2-d][1,4]benzodiazepin-6(7H)-one of m.p. 188°-189° C.

Provenance & Evidence