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 Synthetic Method of Cyclopropyl cyanide
  • Synthetic Method of Cyclopropyl cyanide
  • (CAS no.: ), which is also called as , cyano-, could be produced through the following synthesis routes.

    The apparatus shown in Fig. 10 is assembled in a good hood. One liter of liquid ammonia and 0.5 g. of hydrated ferric nitrate are placed in the 2-l. three-necked flask A, which is equipped with a stirrer and a special reflux condenser cooled with Dry Ice. This condenser is attached to a soda-lime tower which is connected to a source of compressed air through the T-tube C. Over a period of about 45 minutes, 92 g. (4 gram atoms) of clean sodium shavings is added to the liquid ammonia, and the mixture is stirred until the blue color disappears (1–2 hours).

    In the similarly equipped 5-l. three-necked flask B are placed 1.5 l. of liquid ammonia and 440 g. (4.25 moles) of γ-chlorobutyronitrile. The flasks are connected by means of the 12-mm. glass tube D reaching to the bottom of the sodamide flask A and extending 1 cm. through the rubber stopper in one neck of flask B. Vigorous stirring is maintained in both flasks while the sodamide suspension is slowly forced over into the reaction flask in small portions by means of air pressure applied through C; the rate of addition is controlled by placing the finger over the by-pass in the T-tube. At first the reaction is violent, and only small amounts of the sodamide solution should be added. The addition is continued at such a rate that the total time required for addition of all the sodamide solution is 1–1.5 hours. The sodamide flask is rinsed with 300 ml. of liquid ammonia, and the washings are added to the reaction mixture, after which stirring is continued for 2 hours. During the second hour, addition of Dry Ice to the reflux condenser is discontinued, and the ammonia is permitted to evaporate slowly. At the end of the 2-hour stirring period, the inlet tube is replaced by a dropping funnel and 1 l. of dry ether is slowly added. The reaction mixture is quickly filtered through a sintered-glass funnel, and the filter cake is washed with two 200-ml. portions of dry ether. The ammonia and ether are removed by distillation on a water bath through a packed column. The residue is then distilled through the column under the pressure of a water pump. The yield of cyclopropyl cyanide boiling at 69–70°/80 mm. (75–76°/95 mm.) is 149–152 g. (52–53% based upon γ-chlorobutyronitrile). The pressure is then reduced, and the unchanged γ-chlorobutyronitrile is collected at 93–96°/26 mm. It amounts to 52–62 g.


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