1,3-Dichloroacetone → HCID 21265995, compound

Participants

Reaction Steps

A suspension of 2.9 g of 5-phenyl-3H-thieno[3,2-e][1,4]diazepin-2-ylamine, 11.7 g of sodium bicarbonate and 1.83 g of 1,3-dichloroacetone in 80 ml of dioxan was stirred at room temperature under argon for 48 h. Thereafter, the temperature of the reaction mixture was increased to 80° C. and the suspension was stirred under argon for a further 27 h. After cooling to 60° C. 19.2 g of 2.5N sodium hydroxide solution were added and the reaction mixture was stirred under argon for a further 20 h. Subsequently, a further two 19.2 g portions of 2.5N sodium hydroxide solution were added at intervals of twenty hours. The suspension was extracted with dichloromethane/saturated sodium chloride solution in the presence of a small amount of methanol. The dichloromethane extracts were dried with sodium sulphate, filtered and evaporated in a vacuum. The residue was suspended twice in succession in methanol and triturated. There were obtained 2.14 g of crude 4-phenyl-6H-imidazo[1,2-a]thieno[2,3-f][1,4]diazepin-8-ylmethanol which was used without further purification as the free base for the preparation of the dihydrochloride.

Provenance & Evidence