The Reaction of Nitriles under High Pressure. II. The Catalytic Effects of Amines and Water on the Formation of Trisubstituted 1,3,5-Triazines from Nitriles

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When a mixture of benzonitrile and methanol is kept under a high pressure of a few thousand atoms at an elevated temperature, methyl benziminoether is produced and trimerized to triphenyl-1,3,5-triazine. In the present study it was confirmed that the addition of ammonium salts or some nucleophiles with an active hydrogen atom such as water, amines, and ammonia at several per cents in the molar fraction increases the rate of the formation of this triazine by several times. It was found that the nucleophilic benzamidines produced by the reaction of benziminoether with amines attacked the second molecule of the iminoether and successively took the third iminoether molecule to form a triazine ring. The addition of water to the nitrile-methanol mixture produced amidine, methyl ester, amide, and amidinium carboxylate, of which the carboxylate exhibited the highest promotive effect. Some benzamidines were obtained in fairly good yields from amines and benzonitrile under similar high-pressure conditions. It is thought that this could be useful for synthesizing amidines.
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