A 6-polyfluoro alkyl-1,3,5-triazine compound and its synthesis method and application
A polyfluoroalkyl group and a synthesis method technology, which are used in the synthesis of 6-polyfluoroalkyl-1,3,5-triazine compounds, the synthesis of triazine natural products, materials and pharmaceutical intermediates, and the field of medicine , which can solve the problems of human body and environmental hazards, high toxicity of acid chloride, and easy occurrence of danger, and achieve the effect of wide substrate range, simple operation and simple conditions.
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Embodiment 1
[0028] Example 1 2-amino-4-dimethylamino-6-pentafluoroethyl-1,3,5-triazine
[0029] 1. Put metformin hydrochloride (1.0mmol) and sodium hydroxide (1.0eq) into a 25mL round-bottomed flask, inject 3mL of N,N-dimethylformamide solvent, pretreatment neutralize and remove acid to obtain free biguanide. Then, perfluoroiodopropane (1.1 eq) was added at room temperature. 36W household energy-saving lamp irradiation and reaction at room temperature for 5 hours, TLC monitoring until the reaction is complete. The resulting reaction product was poured into 100 mL of water, extracted three times with dichloromethane, the organic phases were combined, and the organic solvent was distilled off under reduced pressure to obtain a crude product;
[0030] 2. The crude product is eluted by silica gel column chromatography with an eluent (petroleum ether: ethyl acetate=1:1 (V:V)), the eluate is collected, and the organic solvent is distilled off under reduced pressure to obtain a white solid , w...
Embodiment 2
[0036] Example 2 2-amino-4-dimethylamino-6-pentadecafluoroheptyl-1,3,5-triazine
[0037]1. Put metformin hydrochloride (1.0mmol) and sodium hydroxide (1.0eq) into a 25mL round-bottomed flask, inject 3mL of N,N-dimethylformamide solvent, pretreatment neutralize and remove acid to obtain free biguanide. Then, perfluorooctane iodide (1.1 eq) was added at room temperature. 36W household energy-saving lamp irradiation and reaction at room temperature for 6 hours, TLC monitoring until the reaction is complete. The resulting reaction product was poured into 100 mL of water, extracted three times with dichloromethane, the organic phases were combined, dried, and the organic solvent was distilled off under reduced pressure to obtain a crude product;
[0038] 2. The crude product was subjected to silica gel column chromatography, eluted with an eluent (petroleum ether: ethyl acetate = 1:1 (V:V)), the eluate was collected, and the organic solvent was distilled off under reduced pressure...
Embodiment 3
[0044] Example 3 2-morpholino-4-amino-6-heptafluoropropyl-1,3,5-triazine
[0045] 1. Put morpholine biguanide hydrochloride (1.0mmol) and sodium hydroxide (1.0eq) into a 25mL round-bottomed flask, inject 3mL of N,N-dimethylformamide solvent, neutralize and remove acid in pretreatment, and obtain free Biguanides. Then, perfluoroiodobutane (1.1 eq) was added at room temperature. 36W household energy-saving lamp irradiation and reaction at room temperature for 8 hours, TLC monitoring until the reaction is complete. The resulting reaction product was poured into 100 mL of water, extracted three times with dichloromethane, the organic phases were combined, dried, and the organic solvent was distilled off under reduced pressure to obtain a crude product;
[0046] 2. The crude product was subjected to silica gel column chromatography, eluted with an eluent (petroleum ether: ethyl acetate = 1:1 (V:V)), the eluate was collected, and the organic solvent was distilled off under reduced...
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