反应详情

A catalytic amount of p-toluenesulfonic acid was added to a solution of 1,4 dibenzoylbenzene 1 (0.286 g, 1 mmol) in anhydrous methanol (10 mL). After stirring at reflux for 10 min, thiosemicarbazide (0.182 g, 2 mmol) was added to the reaction mixture and stirred for 12 h under an inert atmosphere of nitrogen gas. After 12 h, methanol was removed under reduced pressure and 10 mL of water was then added. The products were extracted with ethyl acetate (2×20 mL) and the combined organic phases were washed with brine, dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. Purification using flash chromatography (silica gel, hexanes:ethyl acetate, gradient 70:30) afforded 4-benzoyl benzophenone thiosemicarbazone 4 (0.012 g, 0.033 mmol) in a 3.3% yield. HRMS (ESI) calculated for C21H17N3OSH+ (M+H)+ 360.11651, found 360.11649.

1. temperatureat reflux for 10 min
2. stirringstirred for 12 h under an inert atmosphere of nitrogen gas
3. custommethanol was removed under reduced pressure and 10 mL of water
4. additionwas then added
5. extractionThe products were extracted with ethyl acetate (2×20 mL)
6. washthe combined organic phases were washed with brine
7. dry with materialdried over anhydrous sodium sulfate
8. customthe solvent was removed under reduced pressure
9. customPurification