反应详情

Propargyl bromide (4.16 g.) was added to a suspension of ethyl 2-(2-tritylaminothiazol-4-yl)-2-hydroxyiminoacetate (syn isomer, 10 g.), potassium carbonate (4.84 g.) and N,N-dimethylformamide (22 ml.) under atmosphere of nitrogen gas and stirred at room temperature for 100 minutes. The insoluble substance was filtered off and washed with a little of N,N-dimethylformamide. The filtrate and washing solution were combined together, and water (400 ml.) was added to the solution. After the suspension was extracted with ethyl acetate (400 ml.), the extract was washed with a saturated aqueous solution of sodium chloride and dried over magnesium sulfate. After treating the solution with activated charcoal, the solution was concentrated in vacuo. The residue was triturated with diisopropyl ether. The precipitates were collected by filtration, and washed with diisopropyl ether to give ethyl 2-(2-tritylaminothiazol-4-yl)-2-propargyloxyiminoacetate (syn isomer, 8.34 g.).

1. filtrationThe insoluble substance was filtered off
2. washwashed with a little of N,N-dimethylformamide
3. washThe filtrate and washing solution
4. additionwater (400 ml.) was added to the solution
5. extractionAfter the suspension was extracted with ethyl acetate (400 ml.)
6. washthe extract was washed with a saturated aqueous solution of sodium chloride
7. dry with materialdried over magnesium sulfate
8. additionAfter treating the solution with activated charcoal
9. concentrationthe solution was concentrated in vacuo
10. customThe residue was triturated with diisopropyl ether
11. filtrationThe precipitates were collected by filtration
12. washwashed with diisopropyl ether