The way to obtain 2,5-bis(p-nitrophenyl)pyrimidine

 

(57) Abstract:

Usage: in the chemistry of polymers. The inventive method of obtaining 2,5 bis (p nitrophenyl) pyrimidine. Reagent 1 perchlorate 1 dimethylamino 3 dimethylammonio 2 (p nitrophenyl) propene 1. Reagent 2: hydrochloride p - nitrobenzylidene. The process is conducted in the presence of bases in amounts that provide full or partial neutralization of only 2, with a ratio of 1 2 base 1 1,3 (0,325 1,3), when boiled in methanol for 2 h, the Output 47 of 95% so pl. 287 290°C, the color of the sediment is light beige.

The invention relates to the chemistry of 1,3-diazinone compounds, specifically to an improved process for the preparation of 2,5-bis(p-nitrophenyl)-pyrimidine (I), which can be used for the synthesis of 2,5-bis(p-AMINOPHENYL)pyrimidine, monomer used for obtaining high strength, high modulus and resistant materials (films and fibers) based Homo - and polyimides [1-5]

A method of obtaining 2,5-bis(p-nitrophenyl)pyrimidine (I) condensation of perchlorate 1-dimethylamino-3-dimethylimino-2-(p-nitrophenyl)propene-1 (III) hydrochloride p-nitrobenzamide (III) in methanol in the presence of sodium methylate at a ratio

reagents 1:1,5:2,5, namely the addition of m is 3 h, the Department dropped the precipitate, washing it with methanol and water. The crude yield of the target product 89% [6]

The disadvantage of this method is the side formation of impurities that are difficult are removed during the filtration and washing of the target product and worsen in the future as the monomer 2,5-bis(p-AMINOPHENYL)pyrimidine is obtained from I. to Conduct additional cleanup product by recrystallization from dioxane (1 g of product is taken 70 ml of dioxane) reduces the yield of 2,5-bis(p-nitrophenyl)pyrimidine to 70-78%

The purpose of the invention obtain 2,5-bis(p-nitrophenyl)pyrimidine, suitable for subsequent receipt derivatives without further purification and reducing the consumption of reagents and solvents.

This goal is achieved by carrying out the condensation of perchlorate 1-dimethylamino-3-dimethylimino-2-(p-nitrophe-nil)propen-1 (II) hydrochloride p-nitrobenzamide (III) when the use of reason in amounts that provide full or partial neutralization only hydrochloride p-nitrobenzylidene, when the ratio II III base equal 1:1,3:(0,325-1,3). As grounds except sodium methylate can be used other organic and inorganic oreally carried out by boiling in methanol for 2 h to separate the precipitation, washed it with methanol and water. Output 77-95%

A distinctive feature of the proposed method in comparison with the known is carrying out the condensation at a lower basicity of the reaction medium, which is achieved by the use of sodium methylate in quantities from 0,325 to 1.3 mol of 2.3 mol of reactant (1,0 mol ilmoniemi salt and 1.3 mol hydrochloride) instead of 2.5 moles of sodium methylate 2.5 mol of reactant (1,0 mol ilmoniemi salt and 1.5 mole of the hydrochloride), and possible replacement of sodium methylate to other, cheaper and more convenient to work with organic and inorganic bases (carbonates, bicarbonates, hydroxides of alkali metals and ammonium, dimethylamine). Lowering the basicity of the reaction medium increases the resistance reduction groups, capable of strong environments for different redox transformations, and reduces the formation of colored impurities.

The advantage of the proposed method is to obtain the desired product of high purity, which does not require additional purification that eliminates the stage of recrystallization in a known way and contributes to significant savings in solvents, and, in addition, the proposed method can semiisolated re-methanol filters or their distillates, containing dimethylamine, released in the condensation process.

Obtaining 2,5-bis-(p-nitrophenyl)pyrimidine.

P R I m e R 1. In a three-neck flask of 3 l equipped with a stirrer, reflux condenser and addition funnel, download 2 l of methanol and 131 g (0.65 g-mol) of finely hydrochloride p-nitrobenzylidene, stirred for 10 minutes, add a solution of sodium methylate prepared from 130 ml of methanol and 7.4 g (0.32 g-at) of sodium, and the mixture was vigorously stirred for 20 min, then add in one step 174 g (0.5 g-mol) of perchlorate 1-dimethylamino-3-dimethylimino-2-(p-nitrophenyl)the propene-1, the reaction mixture is heated up to 60-62aboutC, kept at this temperature and vigorous stirring for 2 hours, cooled to room temperature, the precipitate is filtered off, thoroughly washed on the filter with methanol from colored impurities, then with water until neutral. Air-dried in a drying Cabinet at 60aboutC. the Yield of 153 g (95%), so pl. 287-290aboutWith the color of the sediment is light beige.

The purity of the product is confirmed by TLC (Silufol UV-254, eluent chloroform, Rf0,4). Product all characteristics corresponds recrystallized 2,5-bis(p-nitrophenyl)pyrimidine described in [6]
is samigina, 1044 g (3.0 g-mol) of perchlorate 1-dimethylamino-3-dimethylimino-2-(p-nitrophenyl)- propen-1 and sodium methylate, obtained by dissolving 45,0 (1.85 g-at) of sodium in 800 ml of methanol, by repeating the sequence of operations as described in example 1. Receive 867 g of the product I, the output 90% so pl. 287-289aboutWith the color of the sediment is light beige.

P R I m e R 3. The connection I get analogously to example 1 in a 1 l flask when loading 400 ml of methanol, 26,2 g (0,13 g-mol) of the hydrochloride of p-nitrobenzamide, 34.8 g (0.10 g-mol) of perchlorate 1-dimethylamino-3-dimethylimino-2-(p-nitrophenyl)propene-1 and 1.75 g (0,0325 g-mol) of sodium methylate. The yield of 28.4 g (88%), so pl. 289-290aboutC.

P R I m e R 4. The connection I get analogously to example 2, but instead of methanol using a methanol filtrate after separation of the precipitate from example 2. The yield of 920 g (95%), so pl. 287-290aboutC.

P R I m e R 5. The connection I get analogously to example 2, but instead of methanol using the filtrate of example 4, the product yield 899 g (93%), so pl. 287-290aboutC.

P R I m e R 6. The connection I get analogously to example 3, but instead of sodium methylate take 2.6 g (0,065 g-mol) of sodium hydroxide, the product yield of 29.3 g (91%), so pl. 289-290aboutC.

P R I m e R 7. The connection I get a.. 286-289aboutC.

P R I m e R 8. The connection I get analogously to example 6, but instead of sodium hydroxide charge of 3.45 g (0,0325 g-mol) of sodium carbonate, the product yield of 29.4 g (91%), so pl. 286-289aboutC.

P R I m e R 9. The connection I get analogously to example 6, but instead of sodium hydroxide, take 10,9 (0,13 g-mol) of sodium bicarbonate, the product yield 30.0 g (93%), so pl. 286-288aboutC.

P R I m e R 10. The connection I get analogously to example 6, but instead of sodium hydroxide, take 20 ml of 25% aqueous ammonia solution ( 0,13 g-mol), the product yield of 26.8 g (83%), so pl. 288-290aboutC.

P R I m e R 11. The connection I get analogously to example 6, but instead of sodium hydroxide, take 10 ml of 25% aqueous ammonia solution ( 0,065 g-mol), the product yield 24,9 n (77%), so pl. 288-290aboutC.

P R I m e R 12. The connection I get analogously to example 6, but instead of sodium hydroxide charge of 5.8 g (0,13 g-mol) of dimethylamine, which is saturated with methanol, the yield of the product to 29.8 g (92%), so pl. 286-288aboutC.

P R I m e p 13. The connection I get analogously to example 6, but instead of sodium hydroxide charge of 10.1 g (0,13 g-mol) of ammonium bicarbonate, the product yield of 26.6 g (83%), so pl. 285-288aboutC.

Thus, the proposed method can improve the output cinemar high quality;

to simplify the process, due to the absence of operations recrystallization of the target product;

reduce hydrochloride p-nitrobenzylidene from 1.5 to 1.3 mol per 1 mol ilmoniemi salt;

to reduce the consumption of sodium methylate from 2.5 to 0,325 to 1.3 mol per 1 mol ilmoniemi salt;

to replace the sodium methylate at a more accessible, cheap and easy to use inorganic salts of carbonates, bicarbonates, hydroxides of alkali metals and ammonium;

to reduce the consumption of methanol with multiple repetitions of the process, due to the re-use of the methanol filtrate operations condensation.

The invention can be used in the technology of production of high-strength, high-modulus and high-thermostable polymers used in the aerospace field.

The WAY to OBTAIN 2,5-BIS(P-NITROPHENYL)PYRIMIDINE condensation of perchlorate 1-dimethylamino-3-dimethylimino 2-(p-nitrophenyl)propene-1 hydrochloride p-nitrobenzylidene in alcoholic medium in the presence of a base, characterized in that the reaction is carried out at a molar ratio of perchlorate 1-dimethylamino - 3-dimethylimino-2-(p-nitrophenyl)propene-1, hydrochloride p-nitrobenzylidene and the base 1 1,3 (0,325 1,3), and the sodium or dimethylamine.

 

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