反应详情

To a stirred solution of 7.3 grams (0.04 mole) of 3,5-dichloro-4H-1,2,6-thiadiazin-4-one and 9.0 grams (0.04 mole) of a α-cyano-3-phenoxybenzyl alcohol in 130 ml of ethyl acetate was added dropwise a solution of 4.1 grams (0.04 mole) of triethylamine in approximately 40 ml of ethyl acetate. Upon complete addition the reaction mixture was stirred at ambient temperature for 16 hours, then diluted with 100 ml of water to dissolve triethylamine hydrochloride. The organic layer was removed and washed with 100 ml of water, then with 100 ml of an aqueous solution saturated with sodium chloride. The organic layer was dried with magnesium sulfate and filtered. The filtrate was evaporated under reduced pressure to a residual solid. The solid was triturated with absolute ethanol and collected by filtration. The filter cake was washed with hexane and recrystallized from glacial acetic acid. The yield was 5.8 grams (39%) of 3-chloro-5-(α-cyano-3-phenoxybenzyloxy)-4H-1,2,6-thiadiazin-4-one; m.p. 146.5°-147.7° C. The nmr and the ir spectra were consistent with the proposed structure.

1. additionUpon complete addition the reaction mixture
2. customThe organic layer was removed
3. washwashed with 100 ml of water
4. dry with materialThe organic layer was dried with magnesium sulfate
5. filtrationfiltered
6. customThe filtrate was evaporated under reduced pressure to a residual solid
7. customThe solid was triturated with absolute ethanol
8. filtrationcollected by filtration
9. washThe filter cake was washed with hexane
10. customrecrystallized from glacial acetic acid