SU1286597A1 - Method of producing n-octylimidazole - Google Patents

Abstract

The invention relates to substituted imidazoles, in particular the preparation of N-octylimidazole (03), which is used to synthesize biologically active compounds. Increasing the yield and simplifying the process is achieved by using a different starting hydrocarbon. 3 other conditions. Production of 03 is carried out from imidazole and butadiene at 80-100 s in the presence of a catalytic system —C (0) - —CH2C (0) —CH, j-l2: PCL; AHOCyH) (CgHj): CFj-C (0) -OH (in mol x) 1: (2-3) :( 10-15) :( 5-10), in the medium of solvent - toluene, and dimethyl sulfoxide (DMSO) in a volume ratio of 1: 1. Then, the reaction mass at 30–40 ° C and 15–20 atm is hydrogenated with H in the presence of 30% hydrazine hydrate (HD) at a volume ratio of HD: DMSO (1–1.5): 1, followed by separation of the organic layer, cleaning it on evaporation. Get 86% yield 03. Changing the ratios of the components in the catalytic system results in a decrease in output. 1 tab. (L

Description

tc

00 od

ate

;about

The invention relates to an improved process for the preparation of N-octylimidazole, which can be used as an intermediate in the synthesis of biologically active compounds.

The purpose of the invention is to increase the yield of the target product, simplifying the process technology due to the fact that imidazole is reacted with butadiene in the presence of a catalytic system containing palladium acetylacetonate, phosphorus trichloride, diethyl ethoxy aluminum, trifluoroacetic acid in a molar ratio of 1: 2-3: 10 -15: 5-10, when using as an organic solvent a mixture of toluene and dimethyl sulfoxide in a volume ratio of 1: 1, followed by hydrogenation of the reaction mixture at 30-40 ° C, pressure 15-20 atm in the presence of 30% hydrazine hydrate at a volume ratio of hydrazine hydrate: dimethyl sulfoxide, equal to 1-1.5: 1.

The invention is illustrated by the following examples.

PRI me R 1. To Oj05 g (0.015 mmol) Pd (ac ac), 0.04 g (0.3 mmol) PCt and 0.2 ml of butadiene

in 2 MP of toluene in a stream of Ar at -5 ° C, 0.19 g (1.5 mmol) of Et AtOEt is added and stirred for 40 minutes. The catalyst solution is transferred to a steel autoclave containing 2.04 (30 mmol) of imidazole in 2 ml of DMSO and 3.24 g (60 mmol) of butadiene, then heated for 10 hours and added 3 mp of 30% hydrazine hydrate the autoclave is closed, pressed at 20 atN and thermostatic at 40 ° C for 6 hours. Then the organic layer is separated, the aqueous phase is extracted with benzene (20 ml), the organic parts are combined and

allowed through (P act.). The solvent is distilled off and distilled in vacuo. The yield of N-octylimidazole is 4.6 (86%).

N-Octylimidazole (1), b.p. 118 ° C / E, 5 mmHg (ПЗ-ПУ С / Oj25MMpT.cT. Lit. data), 135 ° С / / 4 mmHg,, 4785 (1.4781 lit. data). PMR spectrum (g ppm): 1.1 t (3N, CH,); 1.3 m (12H-CH -); 3.9 m (2H, N); 6.8 m (2H, C H N); 7.2 s (1H, CjHjN) K 180.

Analogously to example 1, other experiments were carried out, the conditions of the experiments and the data obtained are listed in the table.

Table continuation

 In the catalyst with YK (3-octyl) nmidaeol catalyst, Brem conduct tepomerizazin 8 h

 The yield is reduced due to gpdroginolysis.

 The time of hydrogenation is 5 hours. Reaction conditions: 0.05 g Pd (ac ac), -2, {Xi g And Dazhazol, 3.24 g butadiene, toluene 2 ml, DMSO 2 ml, time of melturization 10 hours hydrazine hydrate 30%, hydrogenation time 6 hours.

Claims (1)

1 Claims of invention 35 Phosphorus trichloride PCf, diethylethoxy alumina Et AtOEt, trifluoroks Method for the preparation of N-octylimidazole acid F F CCOOH in molar in the environment of an organic solvent ratio of 1: 2-3: 10-15: 5-10, with when heated, it is distinguished as organic as the fact that, in order to increase the high degree of solvent, toluene and  the progress of the target product and simpler dimethyl sulfoxide in the volumetric ratio of the process technology, imidazole is subjected to 1: 1 exposure followed by hydrogenation with butadiene by grafting the reaction mixture at 80-100 С in the presence of catalytic 30-40 С, pressure 15-20 atm system containing acetylce in the presence of 30% hydrazine hydrate palladium toned Pd (CHjC-CH CCH -), at a volume ratio of hydrazinjl hydrate: dimethyl sulfoxide, equal to  ° 1-1.5: 1. Compiler G.Zhukova Editor M.Nedoluzhenko Tehred A.Kravchuk Proofreader M.Demchik Order 7681/24 Circulation 371 Subscription VNIIPI USSR State Committee for inventions and discoveries 113035, Moscow, Zh-35, Raushsk nab., 4/5