Process and intermediates for the preparation of certain nematicidal sulfonamides
A C1-C8, alkyl technology, used in the preparation of sulfonic acid, sulfonamide preparation, organic chemistry, etc.
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preparation example 1
[0148] Synthesis of Compounds of Formula 3
[0149] A 1 L round bottom flask equipped with an overhead mechanical stirrer, 10 cm glass spring packing, modified Dean-Stark trap, thermometer, condenser, and nitrogen inlet and outlet was charged with p-aminoanisole (67 g ; 0.539 mol) and o-dichlorobenzene (ODCB, 359.4 mL, 5.26 vol). 70% sulfuric acid (98 wt%, 50.1 g, 27.2 ml, 0.501 mol) was added to 20 g of water, and then added dropwise into the reactor while maintaining the internal temperature 97.5% was obtained by HPLC (High Performance Liquid Chromatography).
preparation example 2
[0151] Synthesis of Compounds of Formulas 4 and 5
[0152] A 1 L round bottom flask equipped with an overhead stirrer, thermocouple, and nitrogen inlet / outlet was charged with concentrated hydrochloric acid (30% wt%, 314.2 g, 261.8 mL, 2,585 mol) and water (76.7 mL, 0.88 vol). The wet product of the compound of formula 3 (125.1 g, about 70 wt%, 0.431 mol) was added and the resulting slurry was cooled to <10°C. A solution of sodium nitrite (31.2 g, 98%, 0.444 mol) dissolved in water (87.6 mL) was added slowly and the reaction was stirred for 1 h. Sulfamic acid (2.1 g, 98%, 0.222 mol) was then dissolved in water (43.6 mL), and the solution was added to the reaction mass to form a compound of formula 4.
[0153] Water (87.6 ml) was then added to a second 1 L round bottom flask, followed by copper powder (ca. 150 mesh, 3.4 g, 0.054 mol) and the slurry was stirred at room temperature. The reaction mass was slowly transferred to the copper slurry and stirred for about two hours. ...
preparation example 3
[0155] Synthesis of Compounds of Formula 6
[0156] A 1 L round bottom flask equipped with an overhead mechanical stirrer, Dean-Stark trap, thermometer and condenser was charged with the compound of formula 5 from the last example, followed by toluene (432.1 mL). The resulting slurry is heated to remove moisture. The slurry was cooled to 60°C-65°C and N,N-dimethylformamide (4.1 mL, 0.053 mol) was added to the reactor followed by thionyl chloride (64.2 mL, 0.883 mol). After 2 h, the reaction mass was distilled to about 1 / 2 volume, and toluene (259.3 mL) was added to the slurry, followed by further distillation. The resulting slurry was filtered through a pad of celite (8.6 g) and the pad was washed with toluene (86.4 mL), where the filtrate gave the compound of formula 6.
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