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A reaction was performed at 270° C. for 16 hours by following the procedure of Example 1 while using 80.0 g (0.301 mol) of 3,4,5,6-tetrachlorophthalonitrile in the place of pentachlorobenzonitrile and 0.1 g of sodium hydroxide in the place of potassium hydroxide. After the reaction was completed, the reaction solution was cooled to room temperature and then filtered to remove the suspended potassium chloride and the unaltered potassium fluoride. When the benzonitrile solution as the mother liquor was analyzed by gas chromatography, it was found to contain 55.4 g of 3,4,5,6-tetrafluorophthalonitrile and 0.018 g of benzoic acid fluoride (325 ppm based on the amount of 3,4,5,6-tetrafluorophthalonitrile). The stainless steel reaction vessel showed no discernible sign of corrosion.
A reaction was performed and the reaction product was treated by following the procedure of Example 1 while omitting the addition of sodium hydroxide. When the benzonitrile solution as the mother liquor was similarly analyzed, it was found to contain 0.200 g of benzoic acid fluoride (3600 ppm based on the amount of 3,4,5,6-tetrafluorophthalonitrile). The stainless steel reaction vessel showed a sign of slight corrosion.
Example A 3,4,5,6-Tetrafluorophthalonitrile Anhydrous potassium fluoride (11.0 kg) is added to a 50 gallon stainless steel reactor. The salt is dried under 28 inches vacuum at 115°-138° C. for 48 hours. The salt is cooled to 100° C. and tetramethylenesulfone (19 liters) added followed by tetrachlorophthalonitrile (4.74 kg). The mixture is heated with stirring to 156° C. over a 30 minute period. Heating with vigorous agitation is continued for another 2.5 hours at 135°-162° C. The mixture was cooled to 31° C. (15 minutes) and ice (69 kg) and demineralized water (119 liters) were added. The resulting mixture was stirred 1.5 hours before centrifuging to collect crude product which was washed with demineralized water (120 liters). The crude product was transferred back into the 50 gallon stainless steel still and demineralized water (100 liters) added. The mixture was steam distilled until 80 liters of distillate were collected. The distillate was cooled to 0°-5° C. and the product collected on a centrifuge. The crystals were washed with demineralized water (2*90 liters) to give 2.82 kg wet product: LOD 6.4percent; calculated yield: 74percent. A small sample was dried under vacuum for two days at room temperature; mp 81°-83° C.
With potassium fluoride; In N,N-dimethyl-formamide; at 110℃; for 7h;
With molar ratio: tetrachlorophthalonitrile, anhydrous potassium fluoride, N, N-dimethylformamide = 1.0: 4.0: 20.Tetrachlorophthalic phthalonitrile, anhydrous potassium fluoride, N, N-dimethylformamide into chemical reactor, with stirring by increasing the temperature tetrachloro phthalonitrile, anhydrous potassium fluoride was dissolved in N, N-dimethylformamide and the temperature was raised to 110 , maintaining this temperature for 7 hours the stirring was stopped after the reaction, cooling to room temperature, to obtain a liquid mixture; chemical reactor a liquid mixture in a distillation column, the distillate is tetrafluorophthalonitrile, forthwith fed into the dryer, drying at a temperature of 60 for 2.0 hours and then was fed into the drying mill, pulverized into a powder that is finished.
With potassium carbonate; In N,N-dimethyl-formamide; at 100℃; for 12h;Inert atmosphere;
Under nitrogen gas, 4,5-dichlorophthalonitrile (5.0 mmol), Ethyl vanillate (7.5 mmol), K2CO3 (50.0 mmol) was dissolved in 30 ml of anhydrous DMF and refluxed at 100 for 12 hours. When the reaction was complete, the reaction solution was slowly dropped on ice-water in a dropwise manner. The precipitate was filtered off under reduced pressure, washed with distilled water, and the dried crude product was purified by column chromatography (eluent: MC: MeOH = 15: 1)
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