[C:1]([CH2:3][CH2:4][O:5][CH2:6][CH2:7][C:8]#[N:9])#[N:2].[N-:10]=[N+:11]=[N-:12].[Na+].[Cl-].[NH4+].N.[N-:17]=[N+:18]=[N-:19].[NH4+]>CN(C)C=O>[NH:2]1[C:1]([CH2:3][CH2:4][O:5][CH2:6][CH2:7][C:8]2[NH:19][N:18]=[N:17][N:9]=2)=[N:12][N:11]=[N:10]1
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.).
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