反应详情

A round bottomed flask was charged with 5-(4-chlorophenyl)-3,3,6,7-tetramethyl-1H-thieno[2,3-e][1,4]diazepine-2(3H)-thione (123 mg, 0.353 mmol) and a stir bar. Tetrahydrofuran (10 mL, 0.05 M) was added, and the solution was cooled to 0° C. for the addition of hydrazine hydrate (132 μl, 1.763 mmol). Stirred at room temperature 30 min, at which point both TLC and LC/MS analysis indicated essentially complete consumption of the starting material. Triethylamine (295 μl, 2.115 mmol, 6 equiv) was added, followed by acetic acid chloride (150 μl, 2.115 mmol, 6 equiv) (careful! exothermic!), and the solution stirred at rt 1 h. The solution was diluted with dichloromethane and concentrated for purification by column chromatography (eluting with dichloromethane/methanol/ammonium hydroxide), which yielded (Z)—N′-(5-(4-chlorophenyl)-3,3,6,7-tetramethyl-1H-thieno[2,3-e][1,4]diazepin-2(3H)-ylidene)acetohydrazide as a dark red oil (m/z=389) that was used in the subsequent reaction.

1. customconsumption of the starting material
2. stirringthe solution stirred at rt 1 h
3. concentrationconcentrated for purification by column chromatography (eluting with dichloromethane/methanol/ammonium hydroxide), which