反应详情

A solution of 2.0 grams (0.008 mole) of phenylmethyl 6-chlorosalicylate (prepared in Steps A-D) in 25 grams of dimethylformamide was stirred, and 0.3 gram (0.008 mole) of 60% sodium hydride in mineral oil was added. The addition caused the reaction mixture temperature to rise to 32° C. The reaction mixture was allowed to cool to ambient temperature, at which 1.3 grams (0.008 mole) of 2-chloro-4,6-dimethoxy-1,3,5-triazine was added in one portion. Upon completion of addition, the reaction mixture was stirred at ambient temperature for 4 hours. After this time an aliquot of the reaction mixture was subjected to thin layer chromatography, which indicated the reaction mixture had not gone to completion. The reaction mixture was warmed to 80°-85° C. where it was stirred for about 18 hours. After this time the reaction mixture was cooled to ambient temperature and then was poured into a mixture of 100 mL of aqueous 3N hydrochloric acid and 100 mL of an aqueous solution saturated with sodium chloride. The mixture was o extracted with two 300 mL portions of diethyl ether. The combined extracts were washed with one 250 mL portion of an aqueous solution saturated with sodium chloride. The organic layer was dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to a point where a solid residue appeared. The residue was slurried in 5 mL of diethyl ether and filtered to yield 0.6 gram of phenylmethyl 6-chloro-2-(4,6-dimethoxy-1,3,5-triazin-2-yloxy)benzoate. The nmr spectrum was consistent with the proposed structure.

1. additionThe addition
2. customto rise to 32° C
3. additionwas added in one portion
4. additionUpon completion of addition
5. temperatureThe reaction mixture was warmed to 80°-85° C. where it
6. stirringwas stirred for about 18 hours
7. temperatureAfter this time the reaction mixture was cooled to ambient temperature
8. extractiono extracted with two 300 mL portions of diethyl ether
9. washThe combined extracts were washed with one 250 mL portion of an aqueous solution saturated with sodium chloride
10. dry with materialThe organic layer was dried with magnesium sulfate
11. filtrationfiltered
12. concentrationThe filtrate was concentrated under reduced pressure to a point where a solid residue
13. filtrationfiltered