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Preparation method for N,N'-ferrocenediacetyl-tri(dodecyloxy) benzamide

A technology of dodecyloxyl and diacetyl, which is applied in the field of functional small molecule synthesis, can solve the problems of high cost of benzamide and harsh reaction conditions, and achieve a simple and practical preparation method, low production cost, and few by-products Effect

Inactive Publication Date: 2016-01-13
UNIV OF SCI & TECH BEIJING
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] The present invention solves the technical problems of high cost and harsh reaction conditions for synthesizing N,N'-ferrocene diacetyl-tris(dodecyloxy)benzamide, and therefore provides a kind of N,N'-ferrocene Preparation method of iron diacetyl-tri(dodecyloxy)benzamide

Method used

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  • Preparation method for N,N'-ferrocenediacetyl-tri(dodecyloxy) benzamide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] A kind of N, the preparation method of N'-ferrocene diacetyl group-three (dodecyloxy) benzamide, its concrete steps are as follows:

[0030] (1): 0.92g (5mmol) methyl gallate, 4.2g anhydrous K 2 CO 3 , mix 4.98g KI and 30mL acetone, reflux at 60°C for 2h, then slowly add 3.80g (15.25mmol) 1-bromo-n-dodecane dropwise, continue to reflux for 48h, evaporate the acetone to dryness after the reaction is completed, add 30mL CHCl 3Extract, filter, wash the filtrate 3 times with 2% NaOH solution, then wash 3 times with saturated NaCl solution, and finally wash with anhydrous NaCl solution 2 SO 4 Dry, rotary evaporate to remove CHCl 3 , the product 3,4,5-tris(dodecyloxy)benzoic acid methyl ester 2.79g, yield 81%;

[0031] (2): Add 3.44g (5.0mmol) 3,4,5-tris(dodecyloxy)methyl benzoate, 85% hydrazine hydrate 0.86g (15.0mmol) and 20mL anhydrous Ethanol, stirred at 80°C for 8 hours, cooled and filtered with suction to obtain a white solid, which was recrystallized from ethanol ...

Embodiment 2

[0037] A kind of N, the preparation method of N'-ferrocene diacetyl group-three (dodecyloxy) benzamide, its concrete steps are as follows:

[0038] (1): 0.92g (5.0mmol) methyl gallate, 4.2g anhydrous K2CO3, 4.98gKI and 30mL acetone were mixed and heated to reflux for 2h, then slowly added dropwise 4.36g (17.5mmol) 1-bromo-n-dodecane , reflux for 72h, evaporate the acetone to dryness after the reaction is completed, add 30mLCHCl 3 Extract, filter, wash the filtrate 3 times with 2% NaOH solution, then wash 3 times with saturated NaCl solution, and finally wash with anhydrous NaCl solution 2 SO 4 Dry, rotary evaporate to remove CHCl 3 , 2.86 g of the product 3,4,5-tris(dodecyloxy)methyl benzoate was obtained, and the yield was 83%;

[0039] (2): Add 3.44g (5.0mmol) 3,4,5-tris(dodecyloxy)methyl benzoate, 85% hydrazine hydrate 0.89g (15.5mmol) and 20mL anhydrous Ethanol was refluxed and stirred for 8 hours, cooled and filtered with suction to obtain a white solid, which was rec...

Embodiment 3

[0045] A kind of N, the preparation method of N'-ferrocene diacetyl group-three (dodecyloxy) benzamide, its concrete steps are as follows:

[0046] (1): 0.92g (5mmol) methyl gallate, 4.2g anhydrous K 2 CO 3 , mix 4.98g KI and 30mL acetone, reflux at 60°C for 2h, then slowly add 4.97g (19.95mmol) 1-bromo-n-dodecane dropwise, continue to reflux for 48h, evaporate the acetone to dryness after the reaction is completed, add 30mL CHCl 3 Extract, filter, wash the filtrate 3 times with 2% NaOH solution, then wash 3 times with saturated NaCl solution, and finally wash with anhydrous NaCl solution 2 SO 4 Dry, rotary evaporate to remove CHCl 3 3.00 g of the product 3,4,5-tris(dodecyloxy)methyl benzoate was obtained, with a yield of 87%;

[0047] (2): In a 50mL reaction flask, add 3.44g (5.0mmol) 3,4,5-tris(dodecyloxy)methyl benzoate, 0.59g (10.25mmol) of 85% hydrazine hydrate and 20mL of anhydrous Ethanol, stirred at 80°C for 8 hours, cooled and filtered with suction to obtain a wh...

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Abstract

The invention provides a preparation method for N,N'-ferrocenediacetyl-tri(dodecyloxy) benzamide, and belongs to the field of synthesis of functionally micromolecules. The method comprises the following steps: taking methyl gallate, bromododecane and ferrocene as reaction raw materials, firstly performing substitution and hydrazinolysis on methyl gallate to generate 3,4,5-tri(dodecyloxy)benzoyl hydrazine; performing acylation, acidification and acyl chlorination on ferrocene to generate 1,1'-ferrocenedicarbonylchloride; and finally reacting 3,4,5-tri(dodecyloxy)benzoyl hydrazine with 1,1'-ferrocenedicarbonylchloride, so as to obtain N,N'-ferrocenediacetyl-tri(dodecyloxy)benzamide. The method possesses the characteristics of being mild in reaction conditions, simple in operation, low in cost, high in yield and high in product purity. Additionally, the N,N'-ferrocenediacetyl-tri(dodecyloxy)benzamide possesses good gelling effect and possesses good market application prospect.

Description

technical field [0001] The invention relates to the field of functional small molecule synthesis, in particular to a preparation method of N,N'-ferrocene diacetyl-tris(dodecyloxy)benzamide. Background technique [0002] In recent years, molecular gels, as an important branch of colloid science, have attracted more and more attention based on their unique supramolecular multilevel self-assembly structure and broad potential application prospects. After more than 30 years of rapid development, supramolecular chemistry has become a new discipline that intersects with biology, physics, materials and other disciplines. Recent studies have found that the introduction of some special functional groups on the gel factor can prepare gel materials that are stimuli-responsive to light, electricity, heat, ultrasound, fluorescence, pH, magnetism, fluorine ions, etc. It has huge potential application value in various photosensitive devices, biomaterials, drug delivery, nanomaterial prepa...

Claims

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Application Information

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IPC IPC(8): C07F17/02
Inventor 弓爱君赵云波李晶瑞邱丽娜谢艳萍杨静
Owner UNIV OF SCI & TECH BEIJING
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