3-(2-cyanoethoxy)propanenitrile

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The reaction mixture is advantageously worked up by the following procedure: the 3-dialkylaminopropionitrile I together with the water and the byproduct ethylenecyanohydrin III is isolated, for example, with the aid of a thin film evaporator. Thereafter, the remaining high boiling mixture is neutralized with a dilute mineral acid and the bis-(2-cyanoethyl) ether II is isolated from this mixture by fractional distillation under reduced pressure.

Conditions: temp:5.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Bis-(2-cyanoethyl)ether 186 g (1.5 mole), 215 g of sodium azide and 177 g of ammonium chloride were slurried in 1070 ml of dimethylformamide. The mixture was heated at 118°-122° C. with stirring and under reflux for 24 hr. (since ammonia and some ammonium azide are evolved, the heating should be done in a hood). After the bulk of the solvent had been removed at 80°-90° C. and 25 mm pressure, the residue was first heated to boiling with 500 ml of water and 40 ml of concentrated hydrochloric acid, then cooled to 5° C. (Caution: some hydrazoic acid is liberated). The product was filtered, washed twice with cold water and dried; 287 g (91%). Recrystallization of 5 g from 85 ml of water furnished coarse blades, m.p. 199°-200° C. (dec.). The mixture was heated at 118°-122° C. under reflux for 24 hr After the bulk of the solvent had been removed at 80°-90° C. 25 mm pressure, the residue was first heated The product was filtered washed twice with cold water dried Recrystallization of 5 g from 85 ml of water furnished coarse blades, m.p. 199°-200° C. (dec.)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The reaction mixture is advantageously worked up by the following procedure: the 3-dialkylaminopropionitrile I together with the water and the byproduct ethylenecyanohydrin III is isolated, for example, with the aid of a thin film evaporator. Thereafter, the remaining high boiling mixture is neutralized with a dilute mineral acid and the bis-(2-cyanoethyl) ether II is isolated from this mixture by fractional distillation under reduced pressure.