SU514824A1 - Method for preparing 3-acyl-9-vinylcarbazoles - Google Patents

Description

one

A method is proposed for the preparation of new derivatives of carbazole, which can be used in the synthesis of polymeric materials.

A known method for the preparation of unsubstituted 9-vinylcarbazole by pyrolysis of 9- {Ot-acetoxyethyl) carbazole.

However, in the literature, there are no reports on the preparation of 3-acyl 9 vinylcarbazoles, which can be used as monomers for the preparation of photo-pupductors.

3 Acyl-9-.vinylcarbazoles cannot be obtained by a known method, since the glyolysis of the co-derivatives of the 3-acylcarbazoloB is accompanied by the resinification of the npOjCQTiTOB reaction.

The proposed method of obtaining 3 "Ash1-. -9 vinylcarbazoles imply that the 3-acyl-9 (D-hydroxyethyl) carbazole aryl sulfonate is reacted with solid potassium hydroxide when heated, at the boiling point of the reaction mixture, in an organic solvent, for example, in xylene. It is usually carried out from

water race. After the completion of the reaction, the xyl is distilled off; the desired products are washed

water, extracted with ether or chloroform, then the solvent is distilled off; 5pot and the desired products are isolated by conventional means with yields of 60-8O%.

The proposed method can also be obtained 9-vinylcarbazole.

Example 1. 3-Kapril-9-.Vinylcarbazole.

9.8 g (0.02 mol) of tosilata Z-capriple-9 () 3 -oxyethyl) carbazole and 3.4 g of powdered caustic potash are boiled in 50 ml of dry xylene in a flask with a stirrer and a reflux condenser equipped with a Dina-trap Stark, for 1.5 hours. Then the solvent was distilled off, the residue was washed with water and extracted with ether. The ether solution is dried, the ether is distilled off, and the residue is recrystallized from ethanol / ether (1: 1). Obtain 5.2 g of 3-Kapril-9-vinylcarbazole (81% of theoretical), so pl. 39-4О, 5 ° С (from a mixture of ethanol and ether). 5148 Found,%: N С; N 4.38. Calculated, ° / Example 2. 3-4 aproyl-9-vinylcarbazop. To 4.49 g of 3-caproyl-9-. (J8-hydroxyethyl) carbazole benzopuponate, add 1.6 powdered potassium hydroxide and 45 ml of dry xylene. The mixture was boiled in a flask equipped with a stirrer, a reflux condenser and a Dean-Stark trap for 2 hours. The solvent is then distilled off, the residue is washed with water and extracted with ether. After drying the ether solution, the ether is distilled off, and the residue is recrystallized from a mixture of ethanol and ether (1: 1). The output of 3-caproyl-3-vinylcarbazole 1.8 g (62%), so pl. 50-51.5 C (from a mixture of ethanol and ether (1: 1), Found,%: N 5.13. Calculated: N 4.80. Example 3. 3-Stearoyl-9-vinyl-carbazop. 6, 3 g (0.01 mol) of tosylate 3-stearoyl-9 (α-hydroxyethyl) carbazole and 1.6 g of powdered caustic potash are boiled for 2 hours in 50 ml of xylene in a flask equipped with a Dean-Stark interfering trap. Then the solvent distilled off, the residue is washed with water and extracted with chloroform. After distillation of chloroform, the residue is recrystallized from ethanol. 3.6 g of 3-stearoyl 9-vinylcarbazole are obtained, yield 78%, mp 67-69 ° C (from ethanol). Found,% : N 3.4O. С32 "45 ° Calculated,% i N 3.05. In the infrared: Absorption bands with frequencies of 1650 cm (CH CH-) and 1680 () are present in the spectra of the compounds obtained. Formula 1. The method for producing 3-acyl-9-vinylcarbazoles, characterized in that 3-acyl 9- (-oxyethyl) carbazole aryl sulfonate is subjected to interaction with solid potassium hydroxide when heated in an organic solvent followed by separation of the desired product. 2. Method of hygiene, about one third, and so that xylene is used as the solvent and the process is carried out at the boiling point of the solvent .