p-Tricyanovinyl-N,N-dimethylaniline (CAS no.: ), which is also called as Ethenetricarbonitrile, p-dimethylaminophenyl, could be produced through the following synthesis route.

A solution of 26.6 g. (28 ml., 0.22 mole) of N,N-dimethylaniline in 65 ml. of dimethylformamide is placed in a 250-ml. beaker clamped about 30 cm. above the base of a ring stand. The beaker is provided with a mechanical stirrer and thermometer. An iron ring is attached to the ring stand below the beaker so that the temperature of the reaction mixture can be controlled by raising or lowering an ice bath or hot water bath. Recrystallized tetracyanoethylene (p. 877) (25.6 g., 0.20 mole) is added in small portions over a period of about 5 minutes with good stirring. The rate of addition is such as to maintain the temperature at 45–50°, and occasional cooling with an ice bath may be necessary to keep the temperature within this range.

When all the tetracyanoethylene has been added, the reaction mixture is stirred at 45–50° for 10 minutes, and heat is supplied as needed by a water bath. p-Tricyanovinyl-N,N-dimethylaniline generally crystallizes out as a dark-blue solid during this period. At the end of the heating period, the mixture is chilled in an ice bath for 30 minutes. The tricyanovinyl compound is collected on a Büchner funnel, pressed dry with the help of a filter dam, and washed successively with 20 ml. of methanol and 40 ml. of ether. It weighs 25–30 g. after being dried in air.

The crude product is purified by recrystallization from 160–180 ml. of acetic acid. The solution is allowed to cool slowly to room temperature, and p-tricyanovinyl-N,N-dimethylaniline is collected on a Büchner funnel and washed successively with 20 ml. of methanol and 40 ml. of ether. The product, 23–26 g. (52–58%), is obtained as dark-blue needles, m.p. 173–175°.

Notice: Because hydrogen cyanide is formed in this reaction, all operations up to the recrystallization of the product should be carried out in a good hood. Contact of tetracyanoethylene with the skin should be avoided.