Water → HCID 20094113, compound

Participants

Reaction Conditions

Reaction Steps

6. A solution of 2.4 ml of chloroacetyl chloride in 10 ml of diethyl ether is added dropwise at 5° C. within 15 min. to a solution of 6.0g of 3-bromo-2-(1H-2-imidazolyl)aniline in 150 ml of dioxan and 6.1 ml of pyridine. The mixture is stirred at 5° C. for 10 min. and then a solution of 0.25 ml of chloroacetyl chloride in 5 ml of diethyl ether is again added dropwise thereto. The mixture is stirred at 10° to 12° C. for a further 30 min. and then treated within 5 min. with a mixture of 75 ml of aqueous 1N sodium hydroxide solution and 150 ml of dioxan. The mixture is stirred at room temperature for 45 min. and then poured into 1 l of water. The mixture is extracted four times with chloroform. The chloroform extracts are evaporated in a vacuum. The oily residue is crystallized from dichloromethane/diethyl ether. 0.99g of 11-bromo-5H-imidazo[1,2-d][1,4]benzodiazepin-6(7H)-one of m.p. 234°-235° C. is obtained. The aqueous phase is evaporated in a vacuum. The residue is taken up several times in ethanol and toluene and evaporated in a vacuum each time. The residue is dissolved in 150 ml of trifluoroacetic acid and left to stand at room temperature for 16 h. The reaction mixture is evaporated in a vacuum and the residue is partitioned between saturated aqueous sodium hydrogen carbonate solution and chloroform. The organic extracts are evaporated in a vacuum and the residue is crystallized from dichloromethane/diethyl ether. There are obtained a further 3.37 of 11-bromo-5H-imidazo[1,2-d][1,4]benzodiazepin-6(7H)-one.

Provenance & Evidence