第2級アミンの新合成法 (第4報)

エチレンジアミン, エタノール-アミン, トリメチレンジアミン及びプロパノールアミン誘導体の合成

抄録

1) N-β-Bromoethylsaccharin and α, β-disaccharinoethane were prepared from saccharin and ethylene dibromide, and converted advantageously to RNHCH₂CH₂NHR, RNHCH₂CH₂NH₂, RNHCH₂CH₂OH, and RNHCH₂CH₂OC₆H₅ by the process shown in Table I.
2) The same procedures as above, using trimethylene dibromide, yielded RNHCH₂CH₂CH₂NHR, RNHCH₂CH₂CH₂NH₂, RNHCH₂CH₂CH₂OH, and RNHCH₂CH₂CH₂OC₆H₅.
3) Non-symmetric alkylethylenediamines were prepared by the chlorination of RNHCH₂CH₂OH to RNHCH₂CH₂Cl, with subsequent application of an amine.
4) Potassium saccharin and ethylene dibromide undergo condensation after being heated at above 200° for a long period of time and the formation of a large amount of disaccharinoethane as a by-product cannot be avoided. The use of dimethylformamide as a solvent in this case yielded N-β-bromoethylsaccharin in 90% yield on being heated on a boiling water bath.