YAKUGAKU ZASSHI
Online ISSN : 1347-5231
Print ISSN : 0031-6903
ISSN-L : 0031-6903
1,2,4-オキサダイアゾール化合物のパラ置換ベンゼンスルホンアミド類の合成
藤田 公司藤井 利幸井手 明雄
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1964 年 84 巻 11 号 p. 1061-1067

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Syntheses of the new sulfonamides, N-(1, 2, 4-oxadiazolyl)-p-substituted benzenesulfonamides, are described. Although the conversion of 5-amino-3-phenyl-1, 2, 4-oxadiazole to the corresponding sulfonamides by the usual techniques was unsuccessful, N1-(3-phenyl-1, 2, 4-oxadiazol-5-yl)sulfanilamide (V) (R=C6H5, X=NH2) was prepared in a low yield by the condensation of sodium of 3-phenyl-5-acetamido-1, 2, 4-oxadiazole and N-acetylsulfanilyl chloride followed by hydrolysis (method 1), and by fusing 5-chloro-3-phenyl-1, 2, 4-oxadiazole and N4-acetylsulfanilamide with potassium carbonate, in a good yield (method 2).
V (R=C6H5, X=CH3 and R=C6H5CH2; X=CH3, NHCOCH3) were also prepared by the method 2.
Alternatively the isomers of V, N1-(5-R-1, 2, 4-oxadiazol-3-yl)sulfanilamide, were synthesized from N1-hydroxyamidino-N4-acetylsulfanilamide (method 3).
The structure of 5-chloro-3-phenyl-1, 2, 4-oxadiazole was discussed from these synthetic evidence.

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