抗黴剤の合成化学的研究 (第10報)

硫黄の存在下における 2-メチルベンゾチアゾールと芳香族第一級アミンおよび芳香族ニトロ化合物との反応について

抄録

Condensation of 2-methylbenzothiazole, having one active methyl group, with six kinds of primary amines substituted with methyl, methoxyl, ethoxyl, isopropoxyl, propoxyl, and butoxyl, in the presence of sulfur, was carried out. Although the yield was different, two forms of thioanilide and bis-benzothiazole were formed from each amine. The same reaction was carried out with nitrobenzene and six kinds of corresponding nitro compounds. Nitrobenzene gave both forms of the product while p-nitrotoluene formed the thioanilide alone. The reaction did not seem to proceed with other compounds probably due to the resistance of the nitro group to reduction to the corresponding amino compounds with nascent hydrogen sulfide produced in the first stage of this reduction. Therefore, electronic considerations were made on the six kinds of para-substituents on the nitro group based on the reduction potential of the nitro group by polarography at pH 4, 6, and 8. Finally, in order to clarify the difference in the chemical structure between the foregoing two forms, ultraviolet spectra of several compounds were measured.