SU632688A1 - Method of obtaining 1,3-bis-(4'-aminophenyl)-adamantane - Google Patents

Description

The process is carried out in an organic solvent, for example, nitrobenzene, and the alkylating product is isolated by distilling nitrobenzene from water with steam. The hydrolysis is carried out in the medium of acetic and sulfuric acids, and the purification of the target product by sublimation. Example. 120 ml of nitrobenzene, 21 g of Desya, 15 g (0.0511 mol) of 1,3-vibro-madaglantan and 11 g (0.0515 mol) of simm-diphenylurea are kept sequentially loaded into the reactor with a stirring device, maintaining the temperature of the reaction mass for 20-25 seconds. 0.5 hour, then the temperature is gradually increased to 8 and the alkylation is carried out under the specified conditions for 5 hours. After the completion of the reaction, the mixture is poured, with stirring and cooling, into sour water. The organic layer is separated. Nitrobenzene is distilled off with steam. The condensation product is separated, cyiuaT and hydrolyzed with a mixture consisting of 165 ml of glacial acetic acid, 22 ml of concentrated sulfuric acid and 5 w of water, in a reactor with stirring device at the boiling point of the solution for 10 hours. After cooling, the reaction mass is poured into water. 1,3-Bis- {4-aminophenyl) -adamantane is isolated by treatment with an aqueous solution of sodium hydroxide or ammonia. The precipitate is filtered off and washed with water. It is dissolved in dilute hydrochloric acid, filtered and re-planted with a solution of alkali; 1,3-bis- (4-aminophenyl} -amantane. It is filtered, washed with water, dried and purified by heat. You-H

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Claims (3)

NH2 od 7.9 g (48% of theoretical in terms of 1,3-dibromadamantan), pl. IVS-lTe C. Found,% g C 82.70; H 8.50; N8.90. Calculated,%: G 82.97; H 8.23; Ijl 8.80. SR - spectrum (80 MHz, SSCC, & ppm relative to HMDS): 7.04; 6.92; 6.42; 6.30; 3.32; 2.20; 2.04; 1.82. Thus, in comparison with the known 3, the proposed two-stage method provides the best yield of the desired product (48 vs. 37%). The invention method for producing 1,3-bis- (4-aminophenyl) -adamantane by alkylation with 1,3-dibromamantane in a solvent medium in the presence of a catalyst, characterized in that, in order to reduce the process stages and increase the yield of the target product, alkylation is subjected to in the presence of aluminum trichloride as catalyzed at 20-85 0 followed by hydrolysis and decarbonylation of the obtained product at boiling in a mixture of acetic and sulfuric acids. Sources of information taken into account in the examination: l.Chewi Bevichte, t. 97, p. 3488, 1964. 2. GLK, vol. 2, no. 4, s. 640-643, 1966, become F.N. Stepanova et al; Adamantane and its derivatives. Substitution reactions in ariladdanthans. 3. USSR author's certificate number 557568, cl. C 07 C 87/46, 1974.