Cyanamide diallyl

After six hours, the solution is cooled to room temperature and a cold solution of 192 g. (4.8 moles) of sodium hydroxide in 350 cc. of water is poured down the side of the flask so that most of it settles to the bottom without mixing with the solution in the flask. The flask is then connected to a condenser for downward distillation and is shaken to mix the two layers. The resulting free amine separates. The flask is heated and the amine, together with some water, distils. The distillation is continued until no amine separates from a test portion of the distillate. There is a small quantity of an oily liquid left floating in the flask. This is probably an impurity from the diallyl cyanamide. 

Diallyl amine has been prepared from allyl amine and allyl bromide,1 and from allyl amine and allyl chloride.2 Experiments on these methods showed that the resulting product contained relatively large amounts of triallyl amine and mono-allyl amine and it was very difficult to isolate pure diallyl amine. The above synthesis from diallyl cyanamide, which has recently appeared in the literature,3 is more satisfactory than the older methods. 

The preparation of diallyl cyanamide by the above method has only recently been described in the literature.1 However, other dialkyl cyanamides have been prepared by the following methods the action of chlorocyanogen or bromocyanogen on dialkyl amines 2 the reaction of dialkylchloroamines with potassium cyanide 3 the action of bromine on a mixture of dialkyl amines and potassium cyanide 4 the action of alkyl halides on disilver cyanamide5 and on disodium cyanamide.6 Dimethyl cyanamide has also been prepared by the action of dimethyl sulfate on lime nitrogen 7 and on cyanamide. 8... 

The reaction of 3jL with 10% excess benzyl bromide or 34 with 10% excess methyl iodide gave the same product, N-benzyl-N-methyl cyanamide (47). The reactions of 33 with 10% and 55% excess allyl bromide afforded N-allyl-N-methyl cyanamide (48) and N,N-diallyl cyanamide (49), respectively. The reaction of 32 with 28% excess of allyl iodide furnished N-allyl-N-propyl cyanamide (50). 

The reaction of i31 with 10% and 55% excess allyl bromide afforded N-allyl-N-methyl cyanaraide (48) and N,N-diallyl cyanamide (49), respectively. 

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