- Production Method of N-Iodosuccinimide
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(CAS NO.: ), which is known as , N-iodo-, could be produced through the following synthetic route.
Twenty grams (0.079 mole) of iodine and 90 ml. of dried dioxane are placed in a wide-mouthed, screw-cap, brown bottle of 150–200 ml. capacity. Most of the iodine dissolves. Eighteen grams (0.087 mole) of thoroughly dried N-silver succinimide is added, and the bottle is shaken vigorously for several minutes. The mixture is occasionally shaken in the course of an hour and then is warmed in a water bath at 50° for 5 minutes. It is now filtered hot through a Büchner funnel into a 500-ml. filter flask well wrapped with black paper or aluminum foil. The silver iodide that is collected is washed with a 10-ml. portion of warm dioxane. tetrachloride (200 ml.) is added to the combined filtrates in the filter flask, and the solution is chilled overnight at -8° to -20°. N-Iodosuccinimide separates as colorless crystals. It is collected on a Büchner funnel with as little exposure to light as possible, washed with 25 ml. of , and dried with suction. After being dried overnight in the dark at 25° (1 mm.) the N-iodosuccinimide weighs 14.3–15.1 g. (81–85% yield) and melts with decomposition at 193–199°.
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