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Biguanide compound and preparation method thereof

A compound and metal alkyl technology, applied in the field of biguanide compounds, can solve the problems of complex production process and low yield of the target product, and achieve the effect of simple synthesis process, low cost and high yield

Inactive Publication Date: 2015-10-07
SHANXI UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The above-mentioned method either has a complex raw material production process, or the yield of the synthetic target product is too low

Method used

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  • Biguanide compound and preparation method thereof
  • Biguanide compound and preparation method thereof
  • Biguanide compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Under the protection of nitrogen, diethylamine (2.00mL, 20.00mmol) was added to 20mL of n-hexane and mixed evenly, stirred at room temperature, and AlMe was added dropwise 3 Toluene solution (2M, 10mL, 20.00mmol) was heated to reflux for 3h to obtain a colorless and clear solution. Cool the above solution to room temperature, add N-(2,6-dimethyl)phenyl-N'-phenylcarbodiimide (8.89g, 40.00mmol), react at room temperature for 1h, quench with water after the reaction is completed, organic The phase was dried over anhydrous sodium sulfate, and the solvent was evaporated by rotary evaporation to obtain the product with a yield of 81%.

Embodiment 2

[0019] Under the protection of nitrogen, diethylamine (2.00mL, 20.00mmol) was added to 20mL n-hexane and mixed evenly, stirred at room temperature, n-BuLi solution in n-hexane (1M, 20.00mL, 20.00mmol) was added dropwise, and After reacting for 1h, a colorless and clear solution was obtained. Cool the above solution to room temperature, add N-(2,6-dimethyl)phenyl-N'-phenylcarbodiimide (8.89g, 40.00mmol), react at room temperature for 1h, and quench with water after the reaction is completed. The organic phase was dried over anhydrous sodium sulfate, and the solvent was evaporated by rotary evaporation to obtain the product with a yield of 75%.

Embodiment 3

[0021] Under the protection of nitrogen, diethylamine (2.00mL, 20.00mmol) was added to 20mL of n-hexane and mixed evenly, stirred at room temperature, and ZnEt was added dropwise 2 Toluene solution (1M, 20.00mL, 20.00mmol) was heated to reflux for 4h to obtain a colorless clear solution. Cool the above solution to room temperature, add N-(2,6-dimethyl)phenyl-N'-phenylcarbodiimide (8.89g, 40.00mmol), react at room temperature for 1h, quench with water after the reaction is completed, organic The phase was dried over anhydrous sodium sulfate, and the solvent was evaporated by rotary evaporation to obtain the product with a yield of 85%.

[0022] Crystal parameters: Chemical formula: C 34 h 38 N 5 , Monoclinic, space group P2(1) / n, unit cell parameters α=90.00°, β=91.965(2)°, γ=90.00°, V=2999.6(5), Z=4. Single crystal structure diagram see figure 1 .

[0023] partial bond length N1-C1 1.278(2), N1-C3 1.413(2), N2-C2 1.399(2), N2-C11 1.422(2), N2-C1 1.432(2), N3-C2 1.2...

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Abstract

The invention provides an N<2>,N<2>-diethyl-N<3>,N<5>-diphenyl-N<1>,N<4>-di(2,6-dimethyl)phenylbiguanide and a preparation method thereof. The method concretely comprises the following steps: adding diethylamine to n-hexane under the protection of an inert gas, uniformly mixing, stirring at room temperature, adding an alkyl metallic compound in a dropwise manner, and carrying out heating refluxing or a normal temperature reaction for 1-5h to obtain a colorless clarified solution; and cooling the solution to room temperature, adding N-(2,6-dimethyl)phenyl-N'-phenylcarbodiimide, carrying out a room temperature reaction for 1h, quenching by using water, drying the above obtained organic phase by using anhydrous sodium sulfate, and carrying out rotary evaporation to remove a solvent in order to prepare a product. The method has the advantages of convenient operation, easy separation and high purity of the product, high yield, low cost, and small pollution to environment.

Description

technical field [0001] The present invention relates to a biguanide compound, in particular to a kind of N 2 ,N 2 -Diethyl-N 3 ,N 5 -Diphenyl-N 1 ,N 4 - bis(2,6-dimethyl)phenylbiguanide compound. Background technique [0002] Biguanide compounds are an important class of intermediates and chemical raw materials for the synthesis of fine chemicals, and are widely used in the fields of medicine, materials and coordination chemistry. Biguanide drugs have a longer history, among which metformin (metformin) was used clinically as early as 1957. In addition to the hypoglycemic effect, its main effects can also improve lipid metabolism, reduce weight, and prevent blood coagulation, etc. . In addition to being used as drugs, biguanide compounds are also widely used in many chemical fields as a very versatile ligand in the field of coordination chemistry due to their multiple coordination sites and flexible coordination positions. The preparation method of the biguanide compo...

Claims

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Application Information

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IPC IPC(8): C07C279/26C07C277/08
Inventor 韩红斐魏学红郭志强
Owner SHANXI UNIV
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