Dichloromethane → HCID 14208259, compound

Participants

Reaction Steps

To a solution of 1,3-dihydro-5-(2-fluorophenyl)-3-amino-2H-1,4-benzodiazepin-2-one (400 mg, 1.49 mmole) in 25 ml of methylene chloride was added p-chlorobenzoyl chloride (380 μl, 3.0 mmole). Triethylamine was added to bring the pH of the reaction mixture to approximately 6 (moist pH paper) followed by 4-dimethylamino pyridine (183 mg, 1.5 mmole). After stirring at room temperature overnight the reaction mixture was diluted with methylene chloride to 200 ml and washed in succession with 10% citric acid solution (3×50 ml), saturated sodium bicarbonate solution, and brine. The organic extracts were dried (MgSO4) and concentrated to give 890 mg of crude product. Silica gel chromatography (hexane-ethyl acetate, 1:1 v/v) afforded the analytical product: m.p. 190°-191° C. TLC: Single spot, Rf =0.70, silica gel (hexane-ethyl acetate, 1:1 v/v).

Provenance & Evidence