Iodine → HCID 70394533, compound

Participants

Reaction Steps

22 g of 5,6-dihydro-5-methyl-4H-imidazo[1,5-a]thieno[3,2-f][1,4]diazepine-one was dissolved in 330 ml of dimethylformamide and treated with 50.6 g of iodine. The mixture was stirred at room temperature for 24 hours and then at 30° for 18 hours. It was then poured into 9 l of saturated aqueous sodium hydrogen carbonate solution. This solution was extracted four times with trichloromethane. The trichloromethane solutions were washed in succession with aqueous sodium thiosulphate solution and with aqueous sodium chloride solution, then dried over sodium sulphate and evaporated in a vacuum. The residue was chromatographed through 2.5 kg of silica gel. An impurity was first eluted with trichloromethane. The main product was then eluted with trichloromethane/ethanol mixtures 199:1 and 99:1. These eluates are evaporated in a vacuum and the residue was crystallized several times from ethyl acetate/diisopropyl ether and then from ethyl acetate. There was obtained 5,6-dihydro-7-iodo-5-methyl-4H-imidazo[1,5-a]thieno[3,2-f][ 1,4]diazepine-one of melting point 175°-177°.

Provenance & Evidence