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 Synthetic Approach of Methanesulfonyl cyanide
  • Synthetic Approach of Methanesulfonyl cyanide
  • sulfonyl cyanide (CAS NO.: ) could be produced through the following synthetic routes.

    Systematic Method of Methanesulfonyl cyanide

    A 2-l., three-necked, round-bottomed flask equipped with a sealed mechanical stirrer, a pressure-equalizing dropping funnel capped with a gas-outlet, and a thermometer is charged with 126 g. (0.500 mole) of sodium sulfite heptahydrate, 84.0 g. (1.00 mole) of sodium hydrogen carbonate, and 1 l. of water. Stirring is begun, and 57.3 g. (0.500 mole) of freshly distilled methanesulfonyl chloride is added dropwise over 30 minutes. The slightly exothermic reaction is accompanied by the evolution of carbon dioxide. After stirring for 2 hours, gas evolution ceases, and a clear, colorless solution of sodium methanesulfinate is obtained.

    The dropping funnel is removed, the solution is cooled to 10° by the addition of ice, and 50 ml. (1.0 mole) of liquid cyanogen chloride is added in one portion with vigorous stirring. Addition of ice keeps the mixture at or below 15°. Within 1 minute the reaction mixture becomes turbid, and methanesulfonyl cyanide separates as a heavy, colorless oil. The mixture is stirred for an additional 15 minutes before 200 ml. of is added. After 3 minutes of stirring, the layers are separated in a 2-l. separatory funnel, and the aqueous layer is extracted with two 100-ml. portions of benzene. The combined extracts are washed with water and dried overnight over anhydrous calcium chloride. Filtration and removal of solvent with a rotary evaporator in a hood affords an almost pure product which is distilled, yielding 35.4–37.8 g. (67–72%) of methanesulfonyl cyanide, b.p. 68–69° (15 mm.),nD20 1.4301, which may be stored in a well-stoppered bottle, kept at or below 0°, for prolonged times without loss in purity.

    Notice: Since cyanogen chloride is highly toxic, the preparation and isolation of the sulfonyl cyanide should be conducted in a well-ventilated hood.
    Benzene has been identified as a carcinogen; OSHA has issued emergency standards on its use. All procedures involving benzene should be carried out in a well-ventilated hood, and glove protection is required.


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