Method for synthesizing monoalkyl phosphite

A technology for monoalkyl phosphonite and compounds, which is applied in the field of synthesis of monoalkyl phosphonite compounds, can solve problems such as low yield and harsh conditions, and achieve increased yield, simple method, The effect of improving reaction efficiency

Inactive Publication Date: 2007-10-17
LIAONING UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Generally speaking, these methods require relatively harsh conditions and the yield is not high.

Method used

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  • Method for synthesizing monoalkyl phosphite
  • Method for synthesizing monoalkyl phosphite
  • Method for synthesizing monoalkyl phosphite

Examples

Experimental program
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Embodiment 1

[0018] Embodiment 1: the synthesis of N-(2-hydroxyethyl) amino-(2'-hydroxyphenyl) methylphosphonic acid monoethyl ester

[0019] Add 0.02 mol of salicylaldehyde and 0.02 mol of ethanolamine into a 100 ml round bottom flask, and reflux for 4 hours under the condition of 30 ml of 95% ethanol as solvent. After adding dropwise a 20ml ethanol solution containing 0.02mol diethyl phosphite, the solution was heated to reflux for 40h. The resulting solid was filtered and washed with ethanol to obtain 2.672 g of a white solid, with a yield of 48.55%.

[0020] The product verification results are as follows:

[0021] 1 H NMR (300MHz, DMSO) δ: 0.97 (CH 3 -,3H), 2.79(-CH 2 -, 2H), 3.49-3.72 (-CH 2 CH 2 -, 4H), 4.64 (-CH-, 1H), 5.33 (-NH-, 1H), 6.84-7.74 (Ar-H, 4H);

[0022] 13 C NMR (300MHz, DMSO) δ: 17.02, 46.77, 54.29, 55.40, 122.72, 95.972, 116.98, 119.73, 129.81, 131.01, 156.50;

[0023] 31 P NMR (300MHz, DMSO) δ: 8.74;

[0024] IR (KBr, cm -1 ): 1604, 1459, 1192, 1077, 104...

Embodiment 2

[0025] Example 2: Synthesis of N-(4-methylphenyl)amino-(2'-hydroxyphenyl)methylphosphonic acid monoethyl ester

[0026] Add 0.02mol of salicylaldehyde and 0.02mol of p-methylaniline into a 100ml round bottom flask, and reflux for 3h under the condition of 30m ethanol as solvent. After dropwise adding 20 ml of ethanol solution containing 0.02 mol of diethyl phosphite, the solution was heated to reflux for 70 h until solid was produced. The resulting solid was filtered and washed with ethanol to obtain 0.932 g of a white solid, with a yield of 14.5%.

[0027] The product verification results are as follows:

[0028] 1 H NMR (300MHz, DMSO): 1.07(-CH 3 , 3H), 2.12(Ar-CH 3 , 3H), 3.88 (O-CH 2 -, 2H), 5.06 (-NH-, 1H), 6.56-7.37 (Ar-H, 8H);

[0029] 13 C NMR (300MHz, DMSO): 16.85, 20.55, 48.16, 62.14, 95.96, 114.55, 119.423, 124.78, 125.60, 128.37, 129.24, 145.60, 155.72;

[0030] 31 P NMR (300MHz, DMSO): 22.12;

[0031] IR (KBr,, cm -1 ): 3394, 1591, 1459, 1221, 1083.

Embodiment 3

[0032] Example 3: Synthesis of N-(2-aminopyridyl)amino-(2'-hydroxyphenyl)methylphosphonic acid monoethyl ester

[0033] Add 0.02 mol of salicylaldehyde and 0.02 mol of 2-aminopyridine into a 100 ml round bottom flask, and reflux for 4 h under the condition of 30 ml of ethanol as solvent. After dropwise adding 20 ml of ethanol solution containing 0.02 mol of diethyl phosphite, the solution was heated to reflux for 36 h until solid was produced. The resulting solid was filtered and washed with ethanol to obtain 2.311 g of a white solid, with a yield of 37.48%.

[0034] The product verification results are as follows:

[0035] 1 H NMR (300MHz, DMSO): 1.06 (CH 3 -,3H), 3.46(-CH 2 -, 2H), 3.74 (-NH-, 1H), 5.20 (-CH-, 1H), 6.56-7.37 (Ar-H, py-H, 8H);

[0036] 13 C NMR (300MHz, DMSO): 16.61, 18.60, 50.33, 56.09, 61.01, 112.05, 117.287, 119.221, 124.575, 128.46, 138.902, 141.894, 154.25, 155.53;

[0037] 31 P NMR (300MHz, DMSO): 16.43.;

[0038] IR (KBr, cm -1 ): 3394, 1591,...

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Abstract

The present invention relates to phosphonous acid monoalkyl ester compound synthesis method. The method is ::adding salicylal and organic amine in 95% ethanol, heating and making it reflux for 3-4 hours, adding diethyl phosphite ethanol solution for continuous reflux for 36-70 hours, filtering white solid, washing it with ethanol, mol ratio of salicylic acid, aromatic amine and diethyl phosphite being 1:1:1. The structure of phosphonous acid monoalkyl ester compound is indicated as formula (I). The inventive method is simple and yield is high.

Description

technical field [0001] The invention relates to a compound synthesis method, in particular to a synthesis method of phosphonous acid monoalkyl ester compounds. Background technique [0002] In recent decades, many theoretical questions on the reaction and structure of organophosphorus compounds have been raised and solved. Due to its importance in biological systems and its wide application in industrial and agricultural production, the research on organophosphorus chemistry has developed rapidly. The variability of phosphorus coordination numbers leads to a large number of phosphorus-containing organic compounds and is very different in structure and function from organic compounds without phosphorus. For this reason, many chemists have done a lot of work in this area, making organic compounds Phosphorus chemistry research and application are increasingly abundant. People have discovered many synthetic methods of organic phosphonates and derivatives, and organic phosphona...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/40C07F9/6533
Inventor 张向东于湛葛春华张晓妍孙丽杰马勇超
Owner LIAONING UNIVERSITY
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