Abstract
1) The melting point of 2-methyl-6-bromobenzothiazole had been rather irregular but was determined as melting at 86-87° by the utilization of ferricyanide oxidation-cyclization of p-bromothioacetanilide and bromine substitution of 2-methyl-6-aminobenzothiazole by the Sandmeyer reaction.2) Application of phosphorus pentasulfide and potassium sulfide to the acetanilide compound was found to be accompanied by the formation of a small amount of aniline as a by-product.3) Dozens of 2-methlybenzothiazole derivatives having ether bonding at 6-position were obtained by the Ullmann reaction of 2-methyl-6-bromobenzothiazole and potassium salt of phenols.4) Some discrepancies were found in the data of 2-methyl-6-phenoxybenzothiazole obtained in the present experiments and those appearing in past literature. In order to find correct data, the compound was submitted to synthetic examinations by the (i) Ullmann reaction of 2-methyl-6-bromobenzothiazole and phenoxides and (ii) oxidative cyclization of 4-phenoxythioacetanilide (m.p. 103-104.5°) with potassium ferricyanide. It was thereby found that the compound melting at 85-87° obtained in the present experiment was the correct one.5) Antifungal tests (chiefly test with Candida) of the intermediates and new compounds failed to reveal any marked substances.
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