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Method for synthesizing dicarboxylic acid N-heterocarbene precursor

A technology of dicarboxylic acid and synthesis method, applied in the direction of organic chemistry, etc., to achieve the effect of large specific surface area, novel structure and large specific surface area

Inactive Publication Date: 2019-03-22
ZUNYI MEDICAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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The compound has not been reported in the literature

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  • Method for synthesizing dicarboxylic acid N-heterocarbene precursor
  • Method for synthesizing dicarboxylic acid N-heterocarbene precursor
  • Method for synthesizing dicarboxylic acid N-heterocarbene precursor

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preparation example Construction

[0025] 1,3-bis[(4-carboxy-3 ', 5'-diisopropyl) biphenyl] the synthetic method of imidazolium chloride salt of the present invention, synthetic steps are:

[0026] Use 2,6-diisopropylaniline and elemental iodine as raw materials to generate 4-iodo-2,6-diisopropylaniline (A) through iodination reaction, and A and p-methoxycarbonylphenylboronic acid undergo Suzuki coupling reaction Generate 4'-amino-3',5'-diisopropyl-(1,1'-biphenyl)-4-methyl carboxylate (B), the synthetic route is as follows figure 2 shown. B and glyoxal are catalyzed by acetic acid to generate 1,4-bis[(4-methoxycarbonyl-3',5'-diisopropyl)biphenyl]-1,4-diaza-1,3 - Butadiene (C), the synthetic route is as image 3 shown. Cyclization of C with paraformaldehyde under the catalysis of anhydrous zinc chloride and hydrochloric acid to generate 1,3-bis[(4-methoxycarbonyl-3',5'-diisopropyl)biphenyl]imidazolium chloride Salt (D), the synthetic route is as Figure 4 shown. D is finally hydrolyzed to obtain the targe...

specific Embodiment

[0028] (i) if figure 2 Shown: Add 2,6-diisopropylaniline (20 mL, 106 mmol), sodium bicarbonate (26.8 g, 219 mmol) and methanol (400 mL) in sequence in a 1000 mL round bottom flask. A solution of iodine (29.6 g, 116.5 mmol) in dichloromethane (200 mL) was then added and stirred at room temperature for 12 hours. Then the solid was filtered, the filter cake was washed with dichloromethane, and the filtrate was concentrated in vacuo to obtain a dark orange oily crude product, which was added with 60 mL of saturated sodium thiosulfate solution and stirred at room temperature for 2 h. 40mL methane extraction 3 times, combined organic layer, anhydrous MgSO 4 Drying and concentration under reduced pressure gave brown oil A (28.3 g) with a yield of 88%.

[0029] Compound A NMR 1 H NMR, 13 C NMR and high-resolution mass spectrometry data: 1 H NMR (400MHz, CDCl 3 )δ7.31(s, 2H), 3.79(s, 2H), 2.86(sept, J=6.8Hz, 2H), 1.27(d, J=6.8Hz, 12H). 13 C NMR (101MHz, CDCl 3 ) δ 140.10, 135....

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Abstract

The invention discloses a method for synthesizing a dicarboxylic acid N-heterocarbene precursor. The method comprises the following steps: by taking 2,6-diisopropy phenylamine as a raw material, enabling the component to react with iodine to generate 4-iodine-2,6-diisopropy phenylamine (A), enabling the A to react with 4-methoxycarbonyl phenylboronic acid with a catalyst in the presence of an inert gas so as to generate 4'-amino-3',5'-diisopropyl-(1,1'-xenyl)-4-methyl formate (B); enabling the compound B to react with oxalaldehyde to generate 1,4-di[(4-methoxycarbonyl-3,5'-diisopropyl) xenyl]-1,4-dinitrogen-1,3-butadiene (C); carrying out a catalytic reaction on the compound C with paraformaldehyde to generate a compound 1,3-di[(4-methoxycarbonyl-3',5'-diisopropyl) xenyl] chloridized imidazole onium salt (D); carrying out a hydrolysis reaction on the compound D, thereby generating a target compound E, namely 1,3-di[(4-carboxyl-3',5'-diisopropyl) xenyl] chloridized imidazole onium salt.

Description

technical field [0001] The invention relates to a synthesis method of a dibasic carboxylic acid N-heterocarbene precursor. Background technique [0002] Metal-organic frameworks are a class of coordination compounds with highly regular and infinitely extended structures formed by organic bridging ligands and metal ions through coordination bonds or other weak forces. Sometimes also called coordination polymers (Coordination polymers). Aromatic dicarboxylic acids have good spatial expansion due to two carboxyl groups in the ortho, meta or para positions, and have a rigid structure that can be used as a bridging ligand to support the network structure, so they are often used as Design and synthesis of metal-organic topology structures. As the MOF-5 reported by Yaghi's research group, using ZnO(CO 2 ) 6 The tetranuclear zinc clusters are SBUs, which are connected with terephthalic acid to construct the holes with a surface area of ​​2900m 2 g -1 , realizing an important...

Claims

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Application Information

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IPC IPC(8): C07D233/60
CPCC07D233/60
Inventor 史大斌张茂元
Owner ZUNYI MEDICAL UNIVERSITY