Tetrahydrofuran → HCID 22099770, compound

Participants

Reaction Steps

A reaction mixture comprising 3.8 g. of lithium aluminum hydride in 100 ml. of dry tetrahydrofuran, 5 g. of 4,9-dihydro-10H-thieno[3,4-b][1,5]benzodiazepin-10-one [U.S. Pat. No. 3,953,430 (Example 25)] and 125 ml. of dry tetrahydrofuran is heated, with stirring under reflux for 18 hours. The reaction mixture is cooled and 4 ml. of water is carefully added dropwise with stirring and ice bath cooling. Following this, 4 ml. of 15% sodium hydroxide and 12 ml. of water are added. The mixture is filtered and the precipitate is washed thoroughly with tetrahydrofuran and ether. The combined organic phases are dried over sodium sulfate filtered and the filtrate is concentrated to dryness. The dark brownish-green crystals are triturated in hexane, filtered, washed with hexane and dried. The product is heated to boiling in 50 ml. of chloroform, filtered and the filtrate is combined with 50 ml. of hexane and cooled in a chill room. The crystals are recovered by filtration, washed with hexane and dried. Recrystallization from chloroform-hexane is repeated. A 200 mg. portion of these crystals is recrystallized by dissolving in 10 ml. of chloroform with warming, treating with activated charcoal, filtering through diatomaceous earth and adding 20 ml. of hexane to the filtrate. These crystals are collected, washed with hexane, and dried giving the desired final product, mp. 167°-169° C.

Provenance & Evidence