反应详情

To the solution of 2-phenyl-4-propargyl-1,3,4-thiadiazolin-5-one (1.6 g, 7.4 mmole) in dry acetone (25 ml) under nitrogen with magnetic stirring was added catalytic amount of silver nitrate 0.1 g, 0.58 mmole), followed by N-iodosuccinimide (1.85 g, 8.15 mmole). The reaction mixture was stirred at room temperature for 20 hours. The solid was filtered off by suction-filtration through a Celite filter. The filtrate was diluted with water (200 ml) and extracted with ethyl acetate (2×100 ml). The organic layer was washed with water (2×50 ml), brine, and dried over sodium sulfate. The drying agent was filtered off and the filtrate was concentrated to give a residue. The residue was triturated with hexane and the product was collected by suction-filtration to give 1.75 g as a semicrystalline compound. m.p.=117°-119° C. Proton NMR spectrum showed the desired compound.

1. filtrationThe solid was filtered off by suction-filtration through a Celite
2. filtrationfilter
3. additionThe filtrate was diluted with water (200 ml)
4. extractionextracted with ethyl acetate (2×100 ml)
5. washThe organic layer was washed with water (2×50 ml), brine
6. dry with materialdried over sodium sulfate
7. filtrationThe drying agent was filtered off
8. concentrationthe filtrate was concentrated
9. customto give a residue
10. customThe residue was triturated with hexane
11. filtrationthe product was collected by suction-filtration
12. customto give 1.75 g as a semicrystalline compound