Zinc complex of asymmetric ethylenediamine-n,n-dipropyonic acid dichloride and method of its obtaining

FIELD: chemistry.

SUBSTANCE: invention relates to zinc complex of asymmetric ethylenediamine-N,N-dipropyonic acid dichloride of formula Also claimed is method of its obtaining. Complex can be applied for solution of problems, associated with the necessity to introduce Zn2+ in chelate form instead of its mineral salts, as well as to serve as initial product for synthesis of other chemical compounds of series of polydentate ligands, in particular asymmetric ethylenediamine-N,N-dipropyonic acid.

EFFECT: obtaining zinc complex of asymmetric ethylenediamine-N,N-dipropyonic acid dichloride.

4 cl, 4 dwg, 3 ex

 

The invention relates to the chemistry of metal complexes with alkylbenzyldimethylammonium acids, so-called complexions and directly related to the zinc complex asymmetric Ethylenediamine-N,N-dipropionate acid dichloride, which can be used in medicine, chemistry and other fields, as well as starting compound for the synthesis of polydentate ligands.

A known number of complexions zinc carboxyl-containing and phosphorus-containing chelating agents used as sources of zinc in chelated form, in particular zinc complexes of Ethylenediamine-N,N,N',N'-tetraoxane and Diethylenetriamine-N,N,N',N",N"-pentauksusnoi acids, as well as oksietilidendifosfonovaya acid (Sergienko, V.S., Aleksandrov, G.G., Afonin Mrs x// Cord. chem., 1997, V.25, No. 2, S; Sergienko, V.S., Afonin Mrs x, Alexandrov,// inch, 1998, T, S; EN 2391348, C07C 227/04, 09.12.2008).

When studying the achieved level of equipment identified description binuclear Nickel complex asymmetric Ethylenediamine-N,N-dipropionate acid of the formula C16H36N4Ni2O12(M. Badea, R. Olar, D. Marinescu//Inorganic Chemistry Communications, 2009, vol. 12, p. 555-557).

As described in the information source specified connection get in two stages. In the first stage, the interaction of the aqueous solution of the primary Lu is ecologo Nickel (Ni 3·2Ni(OH)2) acrylic acid get acrylate Nickel, then formed the acrylate Nickel add Ethylenediamine in an amount corresponding to a molar ratio of Ethylenediamine to acrylic acid of 1:4. The reaction mass is kept in air at room temperature for two weeks, then add dimethylsulfoxide and additionally maintain within two weeks, the precipitated crystal above binuclear Nickel complex asymmetric Ethylenediamine-N,N-dipropionate acid characterized by x-ray diffraction data and elemental analysis, IR spectroscopy, spectra of diffuse reflection.

Described screening99mThe complex compounds in order to identify the radiopharmaceutical suitable for imaging malignant lesions of tissues and organs. Among other investigated complexions have mention99mThe complex asymmetric Ethylenediamine-N,N-dipropionate acid - indicates a lack of this complexant properties of the radiopharmaceutical (Y. Karube, T. Maeda, T. Imoto, M. Ohya// Chemical & Pharmaceutical Bulletin, 1982, vol. 30, No. 7, P. 2529-2533).

Other complexes asymmetric Ethylenediamine-N,N-dipropionate acid is not known. Information concerning the description of the zinc complex asymmetric Ethylenediamine-N,N-dipropionate acid dichloride is, in the literature are missing.

To expand sources of zinc chelate used in various fields of science, medicine, pharmaceuticals, agriculture and other proposed new connection - zinc complex asymmetric Ethylenediamine-N,N-dipropionate acid dichloride having the formula:

and how to obtain it.

The proposed method of obtaining a new connection - zinc complex asymmetric Ethylenediamine-N,N-dipropionate acid dichloride carried out by adding with stirring to the aqueous solution of chloride of zinc equimolar with respect to chloride zinc quantity of Ethylenediamine, after which the reaction mass is then cooled to a temperature of 40-45°C, diluted with water in a volume equal to the volume of the added acrylic acid, then add acrylic acid in 6-10%excess of the stoichiometric amount relative to the contrary, heated the reaction mass to a temperature of 55-60°C and maintained under stirring at this temperature until the selection of the target product. The reaction mass after cooling to a temperature of 40-45°C, diluted with water in a volume equal to the volume of the added acrylic acid. Target product are filtered and washed on the filter with distilled water, then with methanol and dried.

Main characteristic and method of producing the compounds being considered are: a specific sequence of process steps, molar ratio of the starting compounds, the temperature conditions for carrying out the synthesis at different stages of the process.

The proposed method includes several steps. First to aqueous solution of chloride of zinc added under stirring equimolar amounts of ethylene diamine (at a molar ratio of 1:1). The temperature of the reaction mixture rises spontaneously to 85-90°C in the exothermic reaction of complexation of zinc chloride (ZnCl2) with Ethylenediamine. In the first stage of the process gain zinc complex of Ethylenediamine, in which Zn(II) coordinated to two nitrogen atoms of the two amino groups of Ethylenediamine and has the composition C2H8N2Cl2Zn:

At the end of rise of the temperature of the reaction mass is then cooled to a temperature of 40-45°C in order to avoid polymerization at a higher temperature entering the reaction of acrylic acid.

Before the introduction of the acrylic acid in the obtained concentrated solution of Zn(II) complex of Ethylenediamine reaction mass is diluted with water. In case of separation of the target product by filtration diluted, preferably, a volume of water equal to the volume of the added acrylic acid. Otherwise (without dilution with water), the reaction mass thickens, which greatly complicates the allocation generated in the ode synthesis of the target product.

Acrylic acid is added to 6-10%wage excess of the stoichiometric amount relative to the contrary, that compensates for the possible polymerization, the yield of the target product is 58%. The yield of the desired product decreases and amounts to 52% when all other conditions of the process, but the use of stoichiometric quantities of Ethylenediamine and acrylic acid.

The interaction of the zinc complex of Ethylenediamine with acrylic acid is carried out in experimentally determined temperature conditions for maximum yield of the final product, namely at a temperature of 55-60°C. the desired product can be isolated by the known methods, but preferably the most technologically advanced for this method - filtration method. To improve the degree of purity of the isolated product was washed on the filter with distilled water, methanol and dried.

The formation of a new substance - zinc complex asymmetric Ethylenediamine-NM-dipropionate acid dichloride is confirmed by the results of x-ray diffraction and elemental analysis data of mass spectrometry, IR and1H,13With NMR spectroscopy. In the mass spectrum (Fig.1) peak is observed, belonging to the molecular ion 204,961, which corresponds to the molecular mass etilendiamintetrauksusnoy key is lots. The results of x-ray analysis and data13C-NMR spectroscopy reliably confirm the receipt of the proposed method, the zinc complex asymmetric Ethylenediamine-N,N-dipropionate acid. Presence in13C-NMR spectrum of the compounds (2) of the five signals from the five nonequivalent carbon atoms indicates the asymmetric nature of the structure of a molecule, which corresponds to the structure of the Ethylenediamine-N,N-dipropionate acid (CA. EDDP). It should be noted that if the molecule had a symmetrical structure, characteristic of the Ethylenediamine-N,N-dipropionate acid (SIM. EDDP), the number of nonequivalent carbon atoms equal to four and13C-NMR spectrum of the SIM. ADP would be observed four signals. Undeniable proof of receipt of the zinc complex asymmetric Ethylenediamine-N,N-dipropionate acid dichloride were the results of x-ray analysis of the grown single crystal obtained is described by way of the connection.

Data H-NMR spectrum (figure 3), namely the presence of a signal of the protons of methylene group ethylendiamine fragment in the form of a singlet, demonstrate the presence of a plane of symmetry in the structure of the ligand that is part of the complex. The IR spectrum of the complex (Fig. 4) there are absorption bands corresponding to the ionized carb is Xylenol group (1607 cm -1) and the amino group (3151 cm-1).

The compound obtained has TPL 218°C (decomposition). Based on the data of elemental analysis and chelatometric titration found, %: C 28.30, 27,63; H 4.53, was 4.76; N, 8.21, 8,08; Zn 18.95, 19.08; Cl 20.96, 21.10. C8H16N2O4Cl2Zn. Calculated, %: 28.22; N, 4.74; N, 8.23; 0 18.79; Zn 19.20; C1 20.82. The invention is illustrated below by examples and illustrations.

Example 1

45,0 g (0.33 mol) of zinc chloride dissolved under stirring at room temperature 22 cm3water and the resulting solution was added to 19.8 g (22,2 cm3) (0.33 mol) of ethylene diamine. The temperature of the reaction mass rises to 85-90°C due to the exothermic reaction. After raising the temperature of the resulting suspension with stirring, cooled to a temperature of 40°C, dilute with water to volume 48 cm3add of 50.4 g (48,0 cm3) (0.70 mol) of acrylic acid, which corresponds to 6%of th excess in relation to Ethylenediamine. The resulting reaction mass in the form of a solution heated to a temperature of 60°C and kept at this temperature for a period of 2.0 hours the precipitation is filtered off, washed on the filter with distilled water and methanol and dried. Get 65.0 g of zinc complex asymmetric Ethylenediamine-N,N-dipropionate acid dichloride to yield 57%, TPL 218°C (decomposition). Found,%: C 28.30, 27,63; H 4.53, was 4.76; N, 8.21, 8,08; Zn 18.95, 19.08; C120.96, 21.10. C8H16N2O4Cl2Zn. Calculated, %: 28.22; N, 4.74; N, 8.23; 0 18.79; Zn 19.20; Cl 20.82.

Example 2

45,0 g (0.33 mol) of zinc chloride dissolved under stirring at room temperature 22 cm3water and the resulting solution was added to 19.8 g (22,2 cm3) (0.33 mol) of ethylene diamine. The temperature of the reaction mixture due to the exothermic reaction raised to 85-90°C. after raising the temperature of the resulting suspension with stirring, cooled to a temperature of 45°C, diluted with water in a volume of 50 cm3and add the 52.3 g (49,8 cm3) (0.73 mol) of acrylic acid, which corresponds to 10%of th excess relative to the contrary.

The resulting reaction mass in the form of a solution heated to a temperature of 60°C and kept at this temperature for a period of 2.0 hours the precipitation is filtered off, washed on the filter with distilled water and methanol and dried. Get 65.0 g of zinc complex asymmetric Ethylenediamine-N,N-dipropionate acid dichloride to yield 58%, TPL 218°C (decomposition).

Example 3

45,0 g (0.33 mol) of zinc chloride dissolved under stirring at room temperature 22 cm3water and the resulting solution was added to 19.8 g (22,2 cm3) (0.33 mol) of ethylene diamine and the reaction mass is heated to a temperature 85-0°C.

After raising the temperature of the resulting suspension with stirring, cooled to a temperature of 45°C, dilute with water to volume 45 cm3add and 47.5 g (45,2 cm3) (0.66 mol) of acrylic acid, which corresponds to an equimolar amount relative to the contrary. The resulting reaction solution was heated to a temperature of 55°C and maintained at this temperature for 2.5 hours the precipitation is filtered off, washed on the filter with distilled water and methanol and dried. Get to 59.4 g of zinc complex asymmetric Ethylenediamine-N,N-dipropionate acid dichloride to yield 52%, TPL 218°C (decomposition).

Zinc complex asymmetric Ethylenediamine-N,N-dipropionate acid dichloride obtained by the proposed method can be applied to solve problems related to the need for the introduction of zinc in chelated form instead of its mineral salts, and also serve as the starting product for the synthesis of other chemical compounds, in particular polydentate ligands.

Zinc complex asymmetric Ethylenediamine-N,N-dipropionate acid dichloride obtained by the proposed method can be applied to solve problems related to the necessity of Zn2+in chelate form instead of its mineral salts, and also serve as the starting product for the synthesis of other chemically the connections of some polydentate ligands, in particular asymmetric Ethylenediamine-N,N-dipropionate acid.

The results of the preliminary study of the biological activity of the zinc complex asymmetric Ethylenediamine-N,N-dipropionate acid dichloride in oral glucose tolerance test (OGTT) on Wister rats in Scientific-educational center for applied chemical and biological studies, Perm national Polytechnic University showed the manifestation of complex hypoglycemic action.

1. Zinc complex asymmetric Ethylenediamine-N,N-dipropionate acid dichloride of the formula
.

2. The method of obtaining zinc complex asymmetric Ethylenediamine-N,N-dipropionate acid dichloride, namely, that to aqueous solution of zinc chloride was added with stirring equimolar with respect to chloride zinc amount of Ethylenediamine, after which the reaction mass is then cooled to a temperature of 40-45°C, diluted with water, and then add acrylic acid in 6-10%wage excess of the stoichiometric relative to the contrary, heated the reaction mass to a temperature of 55-60°C and maintained under stirring at this temperature until precipitation of the desired product.

3. The method according to claim 2, which consists in the fact that the reaction mass after cooling to a temperature of 40-45°C RA is billaut water volume, equal to the amount added of acrylic acid.

4. The method according to claim 2, which consists in the fact that the target product are filtered, the residue on the filter is washed with distilled water, then with methanol.



 

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