Notes- Decyanoethylation of N,N-Bis(2-cyanoethyl)amides

Abstract

NOTESvol. 24 through Filter Cel. To the yellow filtrate was added 550 ml.ether and the mixture was cooled to 5°. On addition of 49.5 ml. (0.62 mole) of 35% aqueous sodium hydroxide solution, yellow solid separated. This was collected, washed with ether, and dried; yield, 41 g. (69.6%), m.p. 136-140°(uncorr.). Thirty-four g. of the crude base was taken up in 170 ml. dilute hydrochloric acid and the resulting liquid was treated with charcoal and filtered through Filter Cel. After cooling the filtrate to 0-5°, cone, ammonium hydroxide was added until the mixture was neutral. The yellow solid was collected and dried. Details on yield, purification, and properties of the solid are found in Table I.4-Amino-l ,$-dihydro-6-{p-methylthioamlino)-%-( n-propyl)s-triazine. To a warm solution of 8.6 g. (0.0274 mole) 4,6diamino-1,2-dihydro-l-(p-methylthiophenyl)-2-(«-propyl)s-triazine hydrochloride in 86 ml. water was added 11.2 ml. (0.14 mole) 35% aqueous sodium hydroxide. White solid separated immediately which then changed to an oil on further heating. After 1.5 hr. of heating on a steam bath the mixture was cooled to room temperature, whereupon the oil changed to a gum. The supernatant liquid was decanted and the gum was washed once with water. After decantation, as much water as possible was removed in vacuo. Absolute ether was added and the mixture was allowed to stand. The powdery white solid which separated was collected and washed with absolute ether; yield 3 g. (39.4%),