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L-proline trifluoromethanesulfonic acid ammonium salt and application thereof

A technology of proline trifluoromethanesulfonate ammonium salt and trifluoromethanesulfonic acid, which is applied in the direction of sulfonate preparation, carboxylic acid amide preparation, organic compound/hydride/coordination complex catalyst, etc., and can solve the problem of catalyst Difficult to recycle, long reaction time, and limited substrate applicability, etc., to achieve the effect of recyclable price, low cost, and simple process

Inactive Publication Date: 2010-02-24
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] Aminophenol, which is obtained from the three-component condensation reaction of aldehyde, amide and phenol, is a drug intermediate widely used in medicine. The traditional synthesis method mainly uses acidic catalysts to catalyze the synthesis, such as iodine, ferric chloride, p-toluenesulfonate Acid, etc., but it has disadvantages such as long reaction time, difficult recovery of catalyst, and not wide applicability of substrates.

Method used

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  • L-proline trifluoromethanesulfonic acid ammonium salt and application thereof

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Embodiment 1

[0035] Under ice-bath conditions, trifluoromethanesulfonic acid (0.750g, 5.0mmol) was slowly added dropwise to an aqueous solution (10mL) of L-proline (0.580g, 5.0mmol), and the reaction temperature was controlled at -5°C to React at 5°C for 30 minutes, wash with petroleum ether and concentrate to obtain 1.23 g of L-proline trifluoromethanesulfonate ammonium salt with a yield of 93%.

Embodiment 2

[0037] Under ice-bath conditions, trifluoromethanesulfonic acid (0.750g, 5.0mmol) was slowly added dropwise to a toluene solution (10mL) of L-proline (0.580g, 5.0mmol), and the reaction temperature was controlled at -5°C Between ~5°C, react for 30 minutes, wash with petroleum ether and concentrate to obtain 1.14 g of L-proline ammonium trifluoromethanesulfonate, with a yield of 86%.

Embodiment 3

[0039] Add 2-naphthol (0.144g, 1.0mmol), benzaldehyde (0.106g, 1.0mmol), benzamide (0.133g, 1.1mmol) and L-proline ammonium triflate in a 25mL two-necked flask Salt (0.026g, 0.1mmol) was reacted under reflux of chloroform (2mL), followed by TCL. After the reaction, extract with water and ethyl acetate, take the organic layer, concentrate, and recrystallize from ethyl acetate to obtain the corresponding condensation product with a yield of 95%.

[0040] White solid; mp 242-243°C; 1 H NMR (500MHz, DMSO-d 6 ): δ=7.20-7.32(m, 8H, Ar-H), 7.47-7.50(m, 3H, Ar-H), 7.54-7.57(m, 1H, Ar-H), 7.79-7.87(m, 4H , Ar-H), 8.08(d, J=8.5Hz, 1H, Ar-H), 9.03(d, J=8.5Hz, 1H, NH), 10.33(s, 1H, OH); 13 C NMR (100MHz, DMSO-d 6): δ=49.7, 118.8, 119.1, 123.2, 126.9, 127.0, 127.2, 127.6, 128.7, 128.8, 129.0, 129.1, 129.9, 129.1, 129.9, 131.9, 132.8, 134.8, 142.4, 153.6, 16 : 3422, 3147, 1629, 1538, 1400, 1347, 822, 751, 582cm -1 ; MS (ESI): m / z=352 [M - ].

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Abstract

The invention relates to an L-proline trifluoromethanesulfonic acid ammonium salt and an application thereof. The L-proline trifluoromethanesulfonic acid ammonium salt is prepared from trifluoromethanesulfonic acid and L-proline. The L-proline trifluoromethanesulfonic acid ammonium salt can be applied to catalyze a condensation reaction of three components of aldehyde, amide and phenol, wherein the condensation reaction of the three components of the aldehyde, the amide and the phenol is completely carried out in an organic solvent under the action of a trifluoromethanesulfonic acid ammonium salt by using the phenol and the aldehyde and the amine as raw materials, and then reaction liquid is separated and purified to obtain a corresponding multicomponent condensation product. The inventiondevelops a novel trifluoromethanesulfonic acid ammonium salt, thereby promoting the application of acid organic catalysts of a new generation in multicomponent reactions and meanwhile promoting the further development of the multicomponent reactions.

Description

(1) Technical field [0001] The invention relates to a novel trifluoromethanesulfonate ammonium salt--L-proline trifluoromethanesulfonate ammonium salt and its application as a catalyst in the three-component condensation reaction of aldehyde, amide and phenol. (2) Background technology [0002] Ammonium trifluoromethanesulfonate is a new type of acidic organic catalyst. Compared with the traditional Lewis acid (such as aluminum trichloride) and the newly developed rare earth metal Lewis acid catalyst, this organic catalyst has the advantages of being stable to water, requiring only a catalytic amount, no heavy metal pollution, recyclable and cheap. Therefore, it is an efficient green catalyst with good practical application prospects. Since the research team led by Tanabe used diphenylammonium trifluoromethanesulfonate (DPAT) for the first time in 2000 to catalyze the esterification reaction of equivalent carboxylic acids and alcohols, ammonium trifluoromethanesulfonate has...

Claims

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Application Information

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IPC IPC(8): C07D207/16C07C309/06C07C303/32B01J31/02C07C233/73C07C233/18C07C231/12C07D307/52
Inventor 李坚军苏为科卢凌美
Owner ZHEJIANG UNIV OF TECH
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