A green method for the synthesis of α-aminophosphonates catalyzed by brφnsted acidic ionic liquids

An acidic ionic liquid, aminophosphonate technology, applied in chemical instruments and methods, physical/chemical process catalysts, compounds of elements of Group 5/15 of the periodic table, etc., can solve the problem of low reaction yield of electron-withdrawing groups, Problems such as high reaction temperature and long reaction time

Inactive Publication Date: 2011-12-14
XINJIANG UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In most of the reported methods for synthesizing α-aminophosphonate compounds, there are long reaction times, high reaction temperature, use of organic solvents, use of expensive and air-sensitive catalysts, the need to add some special reagents and the use of special Disadvantages such as reaction devices, the biggest shortcoming is that the reaction yield of the electron-withdrawing group attached to the amine is low

Method used

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  • A green method for the synthesis of α-aminophosphonates catalyzed by brφnsted acidic ionic liquids
  • A green method for the synthesis of α-aminophosphonates catalyzed by brφnsted acidic ionic liquids
  • A green method for the synthesis of α-aminophosphonates catalyzed by brφnsted acidic ionic liquids

Examples

Experimental program
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Effect test

Embodiment 1

[0016] Example 1: Acidic ionic liquid [PSb(2-CF 3 Bim)][HSO 4 ] Catalytic synthesis of O, O'-dimethyl-[α-(phenyl)-α-(anilino)]methyl phosphate

[0017] With 2mmol benzaldehyde, 2mmol aniline, 2.2mmol trimethyl phosphite, catalyst 5mol% [PSb (2-CF 3 Bim)][HSO 4 ] was added to a 10mL round-bottomed flask, electromagnetically stirred at room temperature and reacted for 20min until the mixture was solidified, an appropriate amount of distilled water was added to the mixture, the product was stirred and washed with a glass rod, filtered, and the resulting solid was vacuum-dried without recrystallization to obtain the pure product O. O'-Dimethyl-[α-(phenyl)-α-(anilino)]methyl phosphate. Yield 89%. Melting point: 87-90°C.

Embodiment 2

[0018] Example 2: Acidic ionic liquid [PSb(2-CF 3 Bim)][HSO 4 ] Catalytic synthesis of O, O'-dimethyl-[α-(4-chlorophenyl)-α-(anilino)]methyl phosphate

[0019] With 2mmol 4-chlorobenzaldehyde, 2mmol aniline, 2.4mmol trimethyl phosphite, catalyst 5mol% [PSb(2-CF 3 Bim)][HSO 4 ] was added to a 10mL round-bottomed flask, electromagnetically stirred at room temperature and reacted for 20min until the mixture was solidified, an appropriate amount of distilled water was added to the mixture, the product was stirred and washed with a glass rod, filtered, and the resulting solid was vacuum-dried without recrystallization to obtain the pure product O. O'-dimethyl-[α-(4-chlorophenyl)-α-(anilino)]methyl phosphate. Yield 87%. Melting point: 80-82°C.

Embodiment 3

[0020] Example 3: Acidic ionic liquid [PSb(2-CF 3 Bim)][HSO 4 ] catalytic synthesis of O, O'-dimethyl-[α-(4-methoxyphenyl)-α-(anilino)]methyl phosphate

[0021] With 2mmol 4-methoxybenzaldehyde, 2mmol aniline, 2.2mmol trimethyl phosphite, catalyst 5mol% [PSb(2-CF 3 Bim)][HSO 4 ] was added to a 10mL round-bottomed flask, electromagnetically stirred at room temperature and reacted for 15min until the mixture was solidified, an appropriate amount of distilled water was added to the mixture, the product was stirred and washed with a glass rod, filtered, and the resulting solid was vacuum-dried without recrystallization to obtain the pure product O. O'-dimethyl-[α-(4-methoxyphenyl)-α-(anilino)]methyl phosphate. Yield 85%. Melting point: 126-129°C.

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Abstract

The invention relates to a sulfonic acid group functionalized acidic ionic liquid 1-butyl-2-trifluoromethyl-3-sulfonic acid propyl benzimidazole hydrogen sulfate [PSb(2-CF3Bim)][HSO4] A green approach to the catalytic synthesis of α-aminophosphonates. The method has the advantages of simple operation, environmental friendliness, mild reaction conditions, short reaction time, simple post-treatment, high yield and recyclable catalyst.

Description

technical field [0001] The invention relates to a green method for synthesizing α-amino phosphonates, in particular to functionalized sulfonic acid groups Acidic ionic liquid 1-butyl-2-trifluoromethyl-3-sulfopropylbenzimidazolium bisulfate [PSb(2-CF 3 Bim)][HSO 4 ] instead of CF 3 SO 3 H, CF 3 COOH, Mg(ClO 4 ) 2 , Al(ClO 4 ) 3 , Yb(OTf) 3 、BiCl 3 , SmI 2 , GaI 3 , ZrOCl 2 ·8H 2 O and ZrO(ClO 4 ) 2 ·6H 2 O etc traditional A green method for synthesizing α-aminophosphonates with a catalyst or Lewis acid. technical background [0002] α-Aminophosphonate and its derivatives are structurally similar to natural amino acids, and have various functions such as anticancer, antiviral, insecticidal, bactericidal and herbicidal, and growth regulation, and have the advantages of low residue and low toxicity to mammals , so the synthesis of these compounds has attracted much attention. In most of the reported methods for synthesizing α-aminophosphonate compounds, the...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/40B01J31/02
Inventor 刘晨江王斌
Owner XINJIANG UNIVERSITY
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