抗黴剤の合成化学的研究 (第4報)

2-メチル-6-(4-ハロフェニルチオ)ベンゾチアゾール類の合成

抄録

1) In order to find the effect on the bridging sulfur atom in diphenyl sulfide-type compounds by the Sandmeyer reaction, experiments were carried out on 4-(4-nitrophenylthio)aniline. It was thereby found that the use of hydrobromic acid in diazotization, reacted at 0°, chiefly afforded 4-(4-nitrophenylthio)bromobenzene (IV) while the reaction temperature of 0° to 40° chiefly afforded 4-(4-nitrophenylsulfinyl)-bromobenzene (V). The use of conc. nitric acid for diazotization afforded (IV) when the reaction temperature was -20°, but (V) if carried out at 0°.
2) By the electrolytic reduction of 2-methyl-6-(4-nitrophenylthio)benzothiazole (I), its 4-amino compound (II) was obtained in a good yield.
3) The amino compound was submitted to the Sandmeyer reaction by diazotization with hydrobromic acid at 0° and substituted with bromine, chlorine, iodine, and hydroxyl group.
4) Anti-candida tests of these new compounds showed that (II) alone was effective in inhibiting the growth of C. albicans at 10, 000 dilution.