Dimethylformamide → HCID 20392225, compound

Participants

Reaction Steps

An 11.8 g. portion of 4,9-dihydro-10H-thieno[3,4-b][1,5]benzodiazepin-10-one in 175 ml. of dimethylformamide is stirred. A 2.8 g. portion of 50% sodium hydride in mineral oil is treated with hexane to remove the mineral oil and then added to the reaction mixture. After 2 hours of stirring, 6.7 g. (7.2 ml.) of methallyl chloride is added. The mixture is stirred overnight and poured into ice-water. The mixture is extracted with four 250 ml. portions of methylene chloride. The extracts are combined, washed with water, dried over sodium sulfate, filtered and concentrated to dryness. The crude product is dissolved in 10 ml. of 40% methylene chloride in hexane and chromatographed on an alumina column, eluting with the same solvent. Those fractions which contain the desired product as determined by thin layer chromatography are combined and concentrated to give the crude product. This product is heated to solution in 25 ml. of benzene, filtered and the solid which forms is collected, washed with hexane and dried giving the desired product, mp. 161°-163° C.

Provenance & Evidence