Preparation method of N-dihydroxyalkyl cinnamamide

A technology of cinnamamide and dihydroxyalkyl, which is applied in the field of preparation of functional organic compounds, can solve the problems of high cost, high irritation of cinnamoyl chloride, difficult separation of products, etc., and achieves short reaction time, high selectivity and high yield Effect

Inactive Publication Date: 2010-06-16
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] In summary, because the hydroxyl and amino groups in the alkanolamine compound have strong activity, they can react with acid chloride or carboxylic acid group, the selectivity and yield of target product are all low, and the existence of a large amount of by-products makes The product is not easy to separate
In addition, this method also has the problems of high irritation of the reactant cinnamoyl chloride, the need to use a large amount of organic solvents during reaction and separation, lack of environmental friendliness, unsafe operation, and high cost.

Method used

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  • Preparation method of N-dihydroxyalkyl cinnamamide
  • Preparation method of N-dihydroxyalkyl cinnamamide

Examples

Experimental program
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Effect test

Embodiment 1

[0018] According to the molar ratio of 1:2, weigh 8.11g (0.05mol) of methyl cinnamate and 10.50g (0.10mol) of diethanolamine, add them into a 100ml three-neck flask, stir, heat in an oil bath, raise the temperature to 110°C, and add the catalyst Sodium methoxide 0.048g (based on 0.6% wt of methyl cinnamate mass), reacted for 0.5 hour under the condition of a pressure of about 8000Pa to obtain a yellow-green viscous liquid.

[0019] Add 50ml of dichloromethane to dissolve the crude product, add water continuously for extraction, remove the catalyst and unreacted diethanolamine, until the pH value of the aqueous phase is close to 7. The organic phase was separated, and most of the solvent was removed by rotary evaporation, and then vacuum-dried for 48 hours to finally obtain 8.66 g of N,N-dihydroxyethyl cinnamic acid as a white solid, with a yield of 73.8% (calculated as methyl cinnamate).

Embodiment 2

[0021] According to the molar ratio of 1:2, weigh 8.11 g (0.05 mol) of methyl cinnamate and 10.51 g (0.1 mol) of diethanolamine into a 100 ml three-necked flask, and heat the oil bath to 110°C. Add 0.048 g of catalyst sodium methoxide, and react for 1 hour under the condition of a pressure of about 1000 Pa to obtain a yellow-green viscous liquid.

[0022] Add 100ml of brine with a mass fraction of 20% to the crude product. After fully shaking and shaking, the catalyst and unreacted diethanolamine are extracted and removed, the organic phase is separated, and then vacuum-dried for 48 hours to finally obtain N,N-dihydroxyethyl Cinnamamide 5.48g, the yield is 93.4% (calculated as methyl cinnamate).

Embodiment 3

[0024] According to the molar ratio of 1:1.3, 8.11 g (0.05 mol) of methyl cinnamate and 6.83 g (0.065 mol) of diethanolamine were weighed and placed in a 100 ml three-necked flask, and the temperature was raised to 110° C. in an oil bath. Add catalyst sodium methoxide 0.048g, react under the condition of pressure about 8000Pa for 8h, obtain a yellow-green viscous liquid.

[0025] Add 50ml of dichloromethane to dissolve the crude product, add water continuously for extraction, remove the catalyst and unreacted diethanolamine, until the pH value of the aqueous phase is close to 7. The organic phase was separated, dried and filtered by adding anhydrous sodium sulfate, and after most of the solvent was removed by rotary evaporation, vacuum-dried for 48h to finally obtain N,N-dihydroxyethyl cinnamic amide 6.37g with a yield of 54.2% (based on cinnamon acid methyl ester).

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Abstract

The invention discloses a preparation method of N-dihydroxyalkyl cinnamamide, which comprises the following steps of: (1) reacting cinnamamide and glycol amine for 0.5-8 hours in the presence of a catalyst under the condition that the temperature is 80-140 DEG C and the absolute pressure is 1.013*105-103Pa to obtain a crude product, wherein the molar ratio between the cinnamamide and the glycol amine is 1:1-1:2; and (2) adding a sodium chloride water solution or an organic solvent and the sodium chloride water solution into the crude product for extraction, separating an organic phase and a water phase till the water phase is neutral; and removing water or the water and the organic solvent from the organic phase to obtain the N-dihydroxyalkyl cinnamamide. The invention has the advantages of nontoxic and easily obtained raw materials, low use level or non-use of the organic solvent, simple, convenient and safe operation, mild reaction conditions, fewer side reactions, high yield of thetarget product, short reaction time, convenient separation, low cost and the like.

Description

technical field [0001] The invention relates to a preparation method of functional organic compounds, in particular to a preparation method of N-dihydroxyalkyl cinnamamide. Background technique [0002] N-dihydroxyalkyl cinnamic amides are an important class of functional organic compounds, which contain a photosensitive cinnamoyl group and two reactive hydroxyl groups, so they can be used as organic synthesis intermediates and photosensitive polymer materials. Photosensitive functional additives for monomer or polymer materials. In addition, N-dihydroxyalkylcinnamic amides are also useful as muscle relaxants, antibacterial agents, and the like. [0003] N-dihydroxyalkyl cinnamic amides can generally be prepared by reacting cinnamoyl chloride with glycol amine compounds. For example, European Journal of Medicinal Chemistry (39:827, 2004) reported that diethanolamine and cinnamoyl chloride reacted at room temperature for 30min in ether solvent to prepare N, N-dihydroxyethyl...

Claims

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Application Information

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IPC IPC(8): C07C233/22C07C231/02
Inventor吴林波靳春丽
OwnerZHEJIANG UNIV