Carbamyl aromatic acid compound with alkoxy replacing aromatic ring, preparation method and application thereof
A technology for carbamoyl compounds and compounds, applied in the preparation of organic compounds, the preparation of carboxylic acid amides, chemical instruments and methods, etc. ideal, etc.
- Summary
- Abstract
- Description
- Claims
- Application Information
AI Technical Summary
Problems solved by technology
Method used
Image
Examples
Embodiment 1
[0144] Embodiment 1: the preparation of N-(2-decyloxyphenyl) phthamoylbenzoic acid (compound 1)
[0145]
[0146] a) Synthesis of 2-decyloxyaniline:
[0147]
[0148] In the reaction flask, add o-nitrophenol (0.5g, 3.6mmol), acetone 25ml, 1-bromo-decane (0.75ml, 3.6mmol), anhydrous potassium carbonate (1g, 7.2mmol) and an appropriate amount of tetrabutyl bromide ammonium chloride, stirred and refluxed for 18h. After filtration, the filtrate was concentrated under reduced pressure to recover the solvent to obtain a yellow oil, which was directly put into the next step without purification.
[0149] 20 ml of absolute ethanol and 0.2 g of 10% Pd / C palladium carbon catalyst were added to the above residue, and hydrogenation was carried out at atmospheric pressure for 8 h. After filtration, the catalyst was removed, and the filtrate was concentrated and subjected to column chromatography to obtain 0.76 g of a colorless oil, with a yield of 85%.
[0150] 1 H-NMR (CDCl 3 )...
Embodiment 2
[0155] Embodiment 2: the preparation of N-(2-undecyloxyphenyl)-phthalamylbenzoic acid (compound 2)
[0156]
[0157] a) Synthesis of 2-undecyloxyaniline:
[0158]
[0159] In the reaction flask, add o-nitrophenol (0.5g, 3.6mmol), acetone 25ml, 1-bromo-n-undecane (0.8ml, 3.6mmol), anhydrous potassium carbonate (1g, 7.2mmol) and appropriate amount of tetrabutyl Ammonium bromide, stirred and refluxed for 18h. After filtration, the filtrate was concentrated under reduced pressure to recover the solvent to obtain a yellow oil, which was directly put into the next step without purification.
[0160] 20 ml of absolute ethanol and 0.2 g of 10% Pd / C palladium carbon catalyst were added to the above residue, and hydrogenation was carried out at atmospheric pressure for 8 h. Filtrate to remove Pd / C, and the filtrate was concentrated and then subjected to column chromatography to obtain 0.83 g of a colorless oil, with a yield of 87%.
[0161] 1 H-NMR (CDCl 3 ): δ6.813-6.683(m, ...
Embodiment 3
[0166] Embodiment 3: the preparation of N-(2-dodecyloxyphenyl) phthamoylbenzoic acid (compound 3)
[0167]
[0168] a) Synthesis of 2-dodecyloxyaniline:
[0169]
[0170] In the reaction flask, add o-nitrophenol (3.0g, 21.5mmol), acetone 50ml, 1-bromo-n-dodecane (5.2ml, 21.5mmol), anhydrous potassium carbonate (6g, 43.0mmol) and appropriate amount of tetrabutyl Ammonium bromide, stirred and refluxed for 18h. After filtration, the filtrate was concentrated under reduced pressure to recover the solvent to obtain a yellow oil, which was directly put into the next step without purification.
[0171] 50 ml of absolute ethanol and 0.8 g of 10% Pd / C palladium carbon catalyst were added to the above residue, and hydrogenation was carried out at atmospheric pressure for 8 h. After filtering to remove Pd / C, the filtrate was concentrated and subjected to column chromatography to obtain 4.8 g of a colorless oil with a yield of 81%.
[0172] 1 H-NMR (CDCl 3 ): δ6.799-6.685(m, 4H...
PUM
Login to View More Abstract
Description
Claims
Application Information
Login to View More