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Catalyst for amination synthesis of carbodiimide, synthesis method and obtained guanidyl compound

A technology for carbodiimide amine and amine-based compounds, which is applied in the field of guanidine-based compound synthesis, can solve problems such as inability to use on a large scale, poor reaction economy, high cost and the like, and achieves the advantages of being beneficial to large-scale industrial production, short reaction time, The effect of low production cost

Active Publication Date: 2021-09-28
BEIJING INSTITUTE OF TECHNOLOGYGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] As shown in the above method, the method of directly preparing guanidine through the addition reaction of amine and carbodiimide in the prior art often has the following defects: (1) Most of the catalysts used are transition metal catalysts, and most of these transition metal elements belong to Metal elements that are relatively rare and difficult to mine often require high costs in industrial production, and some of them pollute the environment and cannot be used on a large scale; (2) Part of the catalytic process needs to be heated to a higher temperature to To obtain a satisfactory yield, the energy consumption is large, and the reaction economy is relatively poor; (3) the preparation of the catalyst is difficult, and large-scale industrial application cannot be carried out

Method used

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  • Catalyst for amination synthesis of carbodiimide, synthesis method and obtained guanidyl compound
  • Catalyst for amination synthesis of carbodiimide, synthesis method and obtained guanidyl compound
  • Catalyst for amination synthesis of carbodiimide, synthesis method and obtained guanidyl compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] Reaction of Aniline with N,N-Diisopropylcarbodiimide Catalyzed by Lithium Triethylborohydride

[0049] In the glove box, take 0.09313 g (1 mmol) of aniline and 0.1262 g (1 mmol) of N,N-diisopropylcarbodiimide into a dry reaction flask, and then add 0.005 ml of 1mol / L tris The tetrahydrofuran solution of lithium ethyl borohydride was stirred at room temperature for 0.5 hours, left open in the air for 0.5 hours to stop the reaction, added 3 ml of n-hexane to dissolve, and recrystallized to obtain the product with a yield of 99%. And carbon spectrum confirms that gained compound is target compound, as follows:

[0050] 1 HNMR (400MHz, CDCl3) δ = 7.17 (d, J = 7.5Hz, 1H), 6.86 (t, J = 7.4Hz, 1H), 6.82–6.76 (m, 2H), 3.70 (s, 2H), 3.49 ( s,1H),1.10(d,J=6.4Hz,12H);

[0051] 13 C NMR (101MHz, CDCl3) δ=150.32, 150.11, 129.25, 123.54, 121.33, 43.21, 23.36.

Embodiment 2

[0053] Reaction of p-Bromoaniline with N,N-Diisopropylcarbodiimide Catalyzed by Lithium Triethylborohydride

[0054] Take 0.1720 g (1 mmol) of p-bromoaniline and 0.1262 g (1 mmol) of N,N-diisopropylcarbodiimide in the glove box and add it to a dry reaction flask, then add 0.005 ml of 1mol / L with a syringe The tetrahydrofuran solution of lithium triethylborohydride was stirred at room temperature for 0.5 hours, and left open in the air for 0.5 hours to stop the reaction, added 5 milliliters of n-hexane to dissolve, and recrystallized to obtain the product with a yield of 99%. Proton spectrum and carbon spectrum confirm that gained compound is target compound, as follows:

[0055] 1 HNMR (400MHz, CDCl3) δ=7.11(d, J=8.6Hz, 2H), 6.70(d, J=8.6Hz, 2H), 3.67(dt, J=12.7, 6.3Hz, 2H), 3.50–3.45( m,2H),1.08(d,J=6.4Hz,12H);

[0056] 13 C NMR (101 MHz, CDCl3) δ = 149.08, 148.60, 131.11, 124.31, 112.74, 42.13, 22.28.

Embodiment 3

[0058] Reaction of o-Chloroaniline with N,N-Diisopropylcarbodiimide Catalyzed by Lithium Triethylborohydride

[0059] In the glove box, take 0.1720 g (1 mmol) of o-chloroaniline and 0.1262 g (1 mmol) of N,N-diisopropylcarbodiimide into a dry reaction flask, and then add 0.005 ml of 1mol / L with a syringe The tetrahydrofuran solution of lithium triethylborohydride was stirred at room temperature for 0.5 hours, and left open in the air for 0.5 hours to stop the reaction, added 5 milliliters of n-hexane to dissolve, and recrystallized to obtain the product with a yield of 99%. Proton spectrum and carbon spectrum confirm that gained compound is target compound, as follows:

[0060] 1 HNMR (400MHz, CDCl3) δ7.28(dd, J=7.9, 1.3Hz, 1H), 7.07(td, J=7.8, 1.4Hz, 1H), 6.87–6.77(m, 2H), 3.79–3.63(m ,2H),1.12(d,J=6.4Hz,12H);

[0061] 13 C NMR (101 MHz, CDCl3) δ = 156.87, 154.46, 150.71, 137.77, 126.21, 124.52, 122.20, 116.06, 43.31, 23.31.

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Abstract

The invention discloses a catalyst for amination synthesis of carbodiimide, a synthesis method and an obtained guanidyl compound. The catalyst is lithium triethylborohydride. The catalyst disclosed by the invention has the characteristics of low cost, easiness in obtaining, low toxicity, greenness and the like; the high-purity guanidyl compound can be obtained by the synthesis method; and the synthesis method is simple in process, high in yield, high in atom economy and low in energy consumption.

Description

technical field [0001] The present invention relates to the technical field of guanidinium compound synthesis. Background technique [0002] Guanidine is a class of compounds with important physiological activities. Molecules containing guanidine groups often exhibit physiological activities such as antibacterial, antiviral, and enzyme inhibitors. Its skeleton widely exists in drugs and natural products. Guanidine and its derivatives are also an important class of auxiliary ligands, which are widely used in the synthesis of organometallic compounds including main group metals, transition metals and rare earth metals. Guanidine compounds have also been widely used as catalysts in organic synthesis. For example, they can efficiently catalyze Streckers reaction, silylation reaction, Henry reaction, Michael addition, ester synthesis reaction, etc. During the catalytic process, guanidine compounds exhibit It has the advantages of easing the reaction conditions and simplifying th...

Claims

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Application Information

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IPC IPC(8): B01J31/14C07C277/08C07C279/18C07C319/20C07C323/44
CPCB01J31/146C07C277/08C07C279/18C07C319/20C07C323/44C07C2601/14
Inventor 马小莉孙晨光
Owner BEIJING INSTITUTE OF TECHNOLOGYGY
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