4-fatty sulfoamide-2-nitrobenzyl bromide compounds and synthetic method thereof

A technology of nitrobenzyl bromide and sulfonamide group, applied in the field of surfactant synthesis chemistry, can solve problems such as difficulty in chlorosulfonation, and achieve the effects of mild conditions, simple synthesis method and mild reaction conditions

Inactive Publication Date: 2016-01-13
DALIAN UNIV OF TECH
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Problems solved by technology

Its advantage of the synthetic method of this compound of 4-fatty sulfonamide-2-nitrobenzyl bromide of the present invention is to use o-nitrotoluene chlorosulfonation, avoiding o-nitrobenzyl bromide and o-nitrobenzyl alcohol which are difficult to be chlorosulfonated the problem of

Method used

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  • 4-fatty sulfoamide-2-nitrobenzyl bromide compounds and synthetic method thereof
  • 4-fatty sulfoamide-2-nitrobenzyl bromide compounds and synthetic method thereof
  • 4-fatty sulfoamide-2-nitrobenzyl bromide compounds and synthetic method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] (1) Synthesis of intermediate 4-sulfonyl chloride-2-nitrotoluene

[0037] Add 4.64g (0.04mol) of chlorosulfonic acid into the three-necked flask, dropwise add 1.37g (0.01mol) o-nitrotoluene solution below 0°C, and keep stirring below 0°C for 60min. The temperature was programmed to rise to 43°C, and the temperature was maintained for 18 hours. After the reaction, the reaction solution was slowly added dropwise to ice water, a large amount of acid mist was generated, and the lower layer was left standing to form a milky white oily liquid, and then the lower layer was extracted with n-butanol to obtain the n-butanol layer, and the n-butanol was removed. Separated by eluent, 2.06 g of 4-sulfonyl chloride-2-nitrotoluene was obtained with a yield of 87.6%.

[0038] figure 1 It is the mass spectrum of 4-sulfonyl chloride-2-nitrotoluene, where m / z234.0 is the target product [M-H] － Peak, 270.0 is the target product [M+Cl] － peak;

[0039] figure 2It is the H NMR spectru...

Embodiment 2

[0049] (1) Synthesis of intermediate 4-sulfonyl chloride-2-nitrotoluene

[0050] Add 5.80g (0.05mol) of chlorosulfonic acid into the reaction flask, add dropwise 1.37g (0.01mol) o-nitrotoluene solution below 0°C, and keep stirring at 0°C for 50min. The temperature was raised to 38°C, and the reaction temperature was maintained for 17 hours. After the reaction, the reaction solution was slowly added dropwise to ice water, a large amount of acid mist was generated, and the lower layer was left standing to form a milky white oily liquid, and then the lower layer was extracted with ethyl acetate to obtain the ethyl acetate layer, and the ethyl acetate was removed. Separated by eluent, 1.97 g of 4-sulfonyl chloride-2-nitrotoluene was obtained, with a yield of 83.8%;

[0051] (2) Synthesis of intermediate 4-(N,N-di-n-decyl)-sulfonamido-2-nitrotoluene

[0052] Dissolve 1.18g (0.005mol) of the intermediate 4-sulfonyl chloride-2-nitrotoluene in 18mL of chloroform, add 1.48g (0.005mol...

Embodiment 3

[0056] (1) Synthesis of intermediate 4-sulfonyl chloride-2-nitrotoluene

[0057] With embodiment 1 (1).

[0058] (2) Synthesis of intermediate 4-(N-dodecyl)-sulfonamido-2-nitrotoluene

[0059] Dissolve 1.18g (0.005mol) of the intermediate 4-sulfonyl chloride-2-nitrotoluene in 18mL of carbon tetrachloride, add 0.92g (0.005mol) of n-dodecylamine dropwise, raise the temperature to 51°C, and continuously add Adjust the pH to 7-11 with sodium hydroxide, and react for 12 hours; after the reaction, concentrate the reaction solution under reduced pressure, filter it with suction, dry it in vacuum, and separate it with an eluent column to obtain the product 4-(N-dodecyl) -sulfonamido-2-nitrotoluene.

[0060] (3) Synthesis of product 4-(N-dodecyl)-sulfonamido-2-nitrobenzyl bromide

[0061] Dissolve 1.92g (0.005mol) of 4-(N-dodecyl)-sulfonamido-2-nitrotoluene in 20mL of chloroform, add 0.24g of azobisisoheptanonitrile, and heat up to 70-85°C , add sodium bromide 0.51g (0.005mol) in b...

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Abstract

The invention discloses a kind of precursor compounds 4-fatty sulfoamide-2-nitrobenzyl bromide which can form a vesicle and is photodegradable and a synthetic method, and belongs to the field of surfactants. The preparation method comprises adding o-nitrotoluene into chlorosulfonic acid at 0 DEG C, and reacting at 30-80 DEG C to generate 4-chlorosulfonyl-2-nitrotoluene; dissolving the obtained intermediate in a solvent, dropwise adding a long-chain primary amine or secondary amine, adjusting pH to 7-11, and reacting at 30-50 DEG C for obtaining 4-fatty sulfonamide-2-nitrotoluene, performing reduced-pressure concentration on the reaction solution, and performing pumping filtration and drying; and dissolving the product obtained in the above step in a solvent, adding an initiator, adding a brominating agent and reacting at 30-110 DEG C to obtain 4-fatty sulfoamide-2-nitrobenzyl bromide. The synthetic method is simple, the yield of each step of reactions is larger than or equal to 60%, the employed reaction eluant is petroleum ether and ethyl acetate, human body damage is relatively small, and petroleum ether and ethyl acetate are recoverable and reusable, and the synthetic method is friendly to environment.

Description

technical field [0001] The invention relates to 4-fatty sulfonamido-2-nitrobenzyl bromide series compounds and a synthesis method thereof, belonging to the field of surfactant synthesis chemistry. The 4-fatty sulfonamido-2-nitrobenzyl bromide series compound involved in the present invention is a precursor of a class of photolyzable compounds capable of self-assembly to form vesicles, wherein the total number of alkyl carbon atoms is 6-36. Background technique [0002] O-nitrotoluene is an important organic intermediate, and the hydrogen atom on the benzene ring of its structure can be replaced by -SO 3 H, -NH 2 、-SO 2 Cl, -OH and other functional groups are replaced to form o-nitrotoluene derivatives with different properties and uses. [0003] The 4-fatty sulfonamido-2-nitrobenzyl bromide series compounds are synthesized by three-step reactions. In the first step of chlorosulfonation reaction, Chen Zhongxiu of Zhejiang University and others used toluene as raw material...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C311/16C07C303/40
Inventor 乔卫红刘宸宇
Owner DALIAN UNIV OF TECH
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