第2級アミンの新合成法 (第5報)

脂肪族第2級アミンの合成

抄録

1) Since saccharin does not react with alkyl halides under an ordinary pressure, alkylsaccharin has been prepared by reacting under high pressure and temperature. The condensation was successfully concluded at an ordinary pressure by the use of dimethylformamide as a solvent. By the use of this procedure, aliphatic secondary amines possessing a long, straight-chain alkyls (C_nH_2n+1, n=1-12) and branched-chain alkyls (isopropyl, isobutyl, and sec-butyl) were prepared in a good yield.
2) In the case of isopropyl and sec-butyl groups, the product, N-alkylsaccharin, was accompanied with its isomer, O-alkylsaccharin, but the two isomers were separable by the difference of their solubility in ethanol. The isomers can also be separated in the subsequent alkaline hydrolysis.
3) The final hydrolysis procedure was found to be the easiest in the methyl group, becoming increasingly difficult with the increase in the number of carbon atoms in the alkyl chain. When the number of carbon atoms is the same, the hydrolysis is more difficult in the branched-chain alkyl than the straight-chain.