In connection with studies on the correlation of physiological action with chemical constitution the following dibenzofuran derivatives were prepared: 2-and 4-S-aminoethyldibenzofuran, 2and 3-fluorodibenzofuran, 4-dibenzofuryl-N-piperidinomethane, diethyl (3-dibenzofurylamino)ethylmalonate and diethyl (4-dibenzofurylamino)ethylmalonate. The synthesis of 3-and 4-(p-acetamidobenzenesulfonamido)dibenzofuran and of the corresponding amines was also cajrried out. The melting point of the 3-amide differed appreciably from previously recorded values. The interaction of 4-bromodibenzofuran with lithium dimethylamide and lithium diethylamide led to the rearrangement products: 3-dimethylaminodibenzofuran and 3-diethylaminodibenzofuran, respectively.
Like most other raw materials found ill nature, natural waters are often unsuitable for many purposes. In most cases water supplies are not water, but are dilute solutions of chemicals, and in addition often bear colloidal matter, suspended particles, and dissolved gases. Because natural water supplies are rarely suitable as found in nature, such waters are processed by one means or another to yield a product which is suitable for the uses to which it is to be put. Those engaged in supplying water for domestic uses must supply a product which is pleasant to taste, which is clear and without odor, and most important of all, free of harmful substances and organisms.Much water used in industry must meet still further requirements. Some uses demand water which is free of practically all foreign constituents. This last requirement is the most difficult of all to meet. The most common method of producing such water is by evaporation. Another method of producing such water has been described by Bartow (1) and others. This process consists of passing water through an electrolytic cell whereby a product of high quality call be obtained. A new method has been proposed by Adams and Holmes (2). In this process dissolved solids are removed from water by passing it through filters composed of granular organic materials which are best described as "exchangers."The materials described by Adams and Holmes had a fair capacity but were rather expensive. In order to improve this process other entirely different materials have been developed which have excellent physicial properties, high exchange capacity, and are reasonable in cost. They are essentially organic materials manufactured from readily obtainable industrial products. These exchangers are of * Presented at the Buffalo convention June 10, 1937.
June, 1935 AMINO DERIVATIVES OF DIBENZOFURAN 1123 4 , 6 -D i b e n z o f u r m d~ Acid.-Sulfur dioxide was summary added to a suspension of the disodio compound in etherDimetalation of &benzofuran takes place in cooled to -18". After the rapid and complete reaction, the 4,6-positions. The pronounced acidities of the suspension was filtered and the residue dissolved in water. The solution was heated to boiling, Ufered, and the 4-and 6-b'hogens are also reflected in the the filtrate cooled and acidiiied to yield 90% of 4,6-di-metalation of 4-methyldibenzofuran and 4-methbenzofurandisulfinic acid which decomposes a t 183-185'. oxydibenzofuran, each of which undergoes 6-The disulfinic acid was oxidized by POtasSiUm Per-metalation. The predominant, if not exclusive, manganate to 4,6-dibenzofurandisulfonic acid, which was metalation product is heteronuclear and not obtained in a 50% yield and which decomposes a t about 300". homonuclear, as might perhaps have been ex-
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