Acetohydrazide → 1,5-Dimethyl-5,6-dihydro-4H-[1,2,4]triazolo[4,3-a][1,5]benzodiazepine

Participants

Reaction Conditions

Reaction Steps

A disposable tube was charged with 4-methyl-4,5-dihydro-1H-benzo[b][1,4]diazepine-2(3H)-thione (163 mg, 0.848 mmol) and a stirbar. nBuOH (5 mL) was added, followed by acetohydrazide (126 mg, 1.695 mmol), and the solution was stirred at 130° C. overnight. The solution was concentrated and purified by silica gel chromatography (eluting with methylene chloride/methanol/1% ammonium hydroxide) to yield 1,5-dimethyl-5,6-dihydro-4H-benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepine as an off-white amorphous solid (0.126 g, 0.588 mmol, 69%).

Provenance & Evidence