反应详情

To a stirred solution of 0.129 gram (0.00037 mole) of 2-(4-(3,3-dichloroprop-2-enyloxy)-2,6-dichlorophenoxy)acetic acid in 1.9 mL of DMF was added 0.141 gram (0.00037 mole) of HBTU, 0.008 gram (0.00006 mole) of HOBT and 0.24 gram (0.0019 mole) of DIEA. The reaction mixture stirred for 10 minutes at which time 0.075 gram (0.00037 mole) of 3-(trifluoromethyl)benzamidoxime was added. Upon completion of addition the reaction mixture was stirred at ambient temperature then heated to 112° C. where it stirred for four hours. After this time the reaction mixture was cooled to ambient temperature, diluted with water and extracted with a mixture of hexanes and ethyl acetate (70:30). The extract was washed in succession with two 5 mL portions of water, one 5 mL portion of an aqueous hydrochloric acid solution and one 5 mL portion of aqueous sodium bicarbonate, dried with sodium sulfate and filtered. The filtrate was concentrated under reduced pressure to a residue. The residue was purified with column chromatography on silica gel using a mixture of hexanes and ethyl acetate as an eluant. The appropriate fractions were combined and concentrated under reduced pressure, yielding 0.35 gram of the subject compound as an off-white solid.

1. additionwas added
2. additionUpon completion of addition the reaction mixture
3. temperaturethen heated to 112° C. where it
4. stirringstirred for four hours
5. temperatureAfter this time the reaction mixture was cooled to ambient temperature
6. extractionextracted with a mixture of hexanes and ethyl acetate (70:30)
7. washThe extract was washed in succession with two 5 mL portions of water, one 5 mL portion of an aqueous hydrochloric acid solution and one 5 mL portion of aqueous sodium bicarbonate
8. dry with materialdried with sodium sulfate
9. filtrationfiltered
10. concentrationThe filtrate was concentrated under reduced pressure to a residue
11. customThe residue was purified with column chromatography on silica gel using
12. additiona mixture of hexanes and ethyl acetate as an eluant
13. concentrationconcentrated under reduced pressure