Dicyclohexyl trifluoromethanesulfonate ammonium salt and application thereof

A technology of ammonium dicyclohexyltrifluoromethanesulfonate and trifluoromethanesulfonic acid, which is applied in the direction of sulfonate preparation, carboxylic acid amide preparation, formation/introduction of amide groups, etc., and can solve the problem of long reaction time and substrate Low applicability, difficult catalyst recovery, etc., to achieve the effect of low cost, recyclable price, and simple process

Active Publication Date: 2010-02-17
台州小试生物科技有限公司
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  • Abstract
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  • 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 cataly

Method used

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  • Dicyclohexyl trifluoromethanesulfonate ammonium salt and application thereof

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Experimental program
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Effect test

Embodiment 1

[0035] Under ice-bath conditions, trifluoromethanesulfonic acid (0.750g, 5mmol) was slowly added dropwise to a toluene solution (10mL) of dicyclohexylamine (0.905g, 5mmol), and the reaction temperature was controlled at -5°C to 5°C The mixture was reacted for 30 minutes, washed with dichloromethane and concentrated to obtain 1.40 g of dicyclohexylamine ammonium trifluoromethanesulfonate, with a yield of 85%.

Embodiment 2

[0037] Under ice-bath conditions, trifluoromethanesulfonic acid (0.750g, 5mmol) was slowly added dropwise to a cyclohexane solution (10mL) of dicyclohexylamine (0.905g, 5mmol), and the reaction temperature was controlled at -5°C to React at 5°C for 30 minutes, wash with water and concentrate to obtain 1.42 g of ammonium dicyclohexylamine 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 ammonium trifluoromethanesulfonate in a 25mL two-necked flask (0.033g, 0.1mmol), reacted under the reflux condition 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 91%.

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Abstract

The invention relates to a dicyclohexyl trifluoromethanesulfonate ammonium salt and application thereof. The dicyclohexyl trifluoromethanesulfonate ammonium salt is prepared from trifluoromethanesulfonate and dicyclohexylamine. The dicyclohexyl trifluoromethanesulfonate ammonium salt can be applied to catalyzing the condensation reaction of three components such as aldehydes, amide and phenol, the condensation reaction of the three components such as the aldehydes, the amide and the phenol takes the phenol, the aldehydes and the amine as raw materials and is completely finished in an organic solvent under the action of the dicyclohexyl trifluoromethanesulfonate ammonium salt, and the reaction solution is separated and purified to obtain the corresponding multi-component condensation product. The invention develops a novel trifluoromethanesulfonate ammonium salt, promotes the application of a new generation of acid organic catalyst in the multi-component reaction, and promotes the further development of the multi-component reaction.

Description

(1) Technical field [0001] The invention relates to a novel ammonium trifluoromethanesulfonate-dicyclohexyltrifluoromethanesulfonate 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 bee...

Claims

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Application Information

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IPC IPC(8): C07C309/06C07C303/32C07C211/35C07C209/68B01J31/02C07B43/06C07C233/73C07C231/12C07C233/18C07D333/20
Inventor 李坚军施湘君苏为科卢凌美
Owner 台州小试生物科技有限公司
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