Notes 2773 F HgFz I CHjCN -> CH8C=NF + other products Experimental Dichloromalononitrile and N-l, 1-TrichlorocyanoacetimidoylChloride.-A solution of 33.0 g. of malononitrile (0.5 mole) and 500 ml. of water was added to a 1-1. flask equipped with stirrer, thermometer, Dry Ice-acetone reflux condenser, inlet tube, and external ice-water cooling bath. Chlorine gas (118.3 g., 1.67 moles) was introduced slowly with stirring over a period of 4 hr., taking care to keep the temperature at or below 5°. The cooling bath was removed and the stirring was continued another 3 hr., during which time the upper portion of the flask was heated gently with warm air in order to decompose the solid chlorine hydrate. The reaction mixture was then separated. The upper aqueous phase was evaporated to 3.2 g. of white solid, identified as ammonium chloride by infrared spectrum. It gave positive tests for ammonia and chloride ion. The lower, organic phase was fractionated. At atmospheric pressure, 46.9 g. of dichloromalononitrile was collected at 86-93°, with an additional 3.0 g. at 41°when the pressure was reduced to 105 mm. The total yield amounted to 74.0% based on malononitrile. Continuation of the distillation at 45 mm. yielded 8.9 g. (8.5% of theory) of N-l, 1 -trichlorocyanoacetimidoyl chloride boiling at 93-97°.Redistillation at 45 mm. furnished pure material at 97°.

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