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Preparation method of triazine derivative

A technology for triazine derivatives and compounds, applied in the field of preparation of triazine derivatives, can solve problems such as low yield and long route, and achieve the effects of high product quality, shortened process flow and reduced cost

Pending Publication Date: 2018-06-26
JIANGSU SINORGCHEM TECH CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] The main purpose of the present invention is to provide a preparation method of triazine derivatives, to solve the problems of low yield and long route when synthesizing triazine derivatives in the prior art

Method used

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  • Preparation method of triazine derivative
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  • Preparation method of triazine derivative

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preparation example Construction

[0026] The preparation method comprises the following steps: performing substitution reaction on p-nitroaniline and compound A to form intermediate B; performing hydrogenation reduction alkylation reaction on intermediate B and compound C to obtain triazine derivatives; wherein, compound A has The structure shown in formula I, intermediate B has the structure shown in formula II, compound C has the structure shown in formula III, and formula I, formula II and formula III are as follows:

[0027]

[0028] Among them, the R base is C 3 ~C 10 An alkyl group; X is a halogen atom.

[0029] The above-mentioned preparation method provided by the present invention utilizes p-nitroaniline to perform a substitution reaction with compound A, and can replace X in compound A with the amino group in p-nitroaniline to form a trisubstituted triazine, namely intermediate B. Then use the ketone compound of compound C to carry out hydrogenation reduction alkylation reaction with the interme...

Embodiment 1

[0044] (a) Substitution reaction

[0045] Add 0.3mol p-nitroaniline and 225mL 1,4-dioxane into a 1000mL four-neck flask, cool down to 0-5°C, and slowly add cyanuric chloride solution (0.06mol cyanuric chloride dissolved in 180mL 1 , 4-dioxane), after the dropwise addition, the temperature was maintained to continue the reaction for 1h, and then heated to reflux for 1h, and then sodium bicarbonate was added for 2h. After the reaction, the feed solution was washed and filtered to obtain a yellow intermediate 2,4,6-tris-(4-nitroaniline)-1,3,5 triazine (intermediate B). The reaction conversion rate is 99.5%, the reaction selectivity is 98%, and the product purity is 98.5%.

[0046] (b) Hydrogenation reduction alkylation reaction

[0047] Intermediate 29g (0.06mol) 2,4,6-tri-(4-nitroaniline)-1,3,5-triazine, 405g (3.55mol) 5-methyl-2-hexanone, and 3 %Pt / C catalyst 3g (relative to the weight of p-nitroaniline) once drops in the 1L autoclave, respectively with N 2 、H 2 After thre...

Embodiment 2

[0052] (a) Substitution reaction

[0053] Add 0.12mol p-nitroaniline and 200mL N,N-dimethylformamide into a 1000mL four-necked flask, cool down to 0-5°C, and slowly add cyanuric chloride solution (0.04mol cyanuric chloride dissolved in 100mL N,N-dimethylformamide), after the dropwise addition was completed, the temperature was maintained to continue the reaction for 1h. Then heat and reflux for 1 hour, then add sodium bicarbonate to react for 2 hours, the reaction is completed, the material liquid is washed and filtered to obtain the yellow intermediate 2,4,6-tris-(4-nitroaniline)-1,3,5 triazine . The reaction conversion rate is 99%, the reaction selectivity is 98.6%, and the product purity is 97.5%.

[0054] (b) Hydrogenation reduction alkylation reaction

[0055] The intermediate 19.6g (0.04mol) 2,4,6-tri-(4-nitroaniline)-1,3,5 triazine, 270g (2.36mol) 5-methyl-2-hexanone and 3% Pd / C catalyst 6g (relative to the weight of p-nitroaniline) once drops in the 1L autoclave, w...

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Abstract

The invention provides a preparation method of a triazine derivative. The preparation method comprises the following steps: carrying out a substitution reaction on p-nitroaniline and a compound A to form an intermediate B; carrying out a hydrogenation reduction hydrocarbylation reaction on the intermediate B and a compound C to obtain the triazine derivative. According to the preparation method provided by the invention, the triazine derivative is prepared by two steps sequentially comprising substitution and hydrogenation reduction hydrocarbylation, so that not only is the product yield relatively high, but also the technical process is greatly shortened. Meanwhile, due to the adoption of the method, a disubstituted p-phenylenediamine byproduct generated in a traditional process is effectively avoided, it is easy to separate a product, the cost is greatly reduced, no pollution is caused, the quality of the product is high, and it is easy to realize industrialization.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a preparation method of triazine derivatives. Background technique [0002] Triazine derivatives with the following structures are an important class of substances (the R group is C 3 ~C 10 of the alkyl). It is a type of compound formed by substituting and connecting N-substituted p-phenylenediamine on the 1, 3, and 5 carbon atoms of triazine. [0003] [0004] For example, 2,4,6-tris-(N-1,4-dimethylpentyl-p-phenylenediamine)-1,3,5-triazine (TMPPD for short) is an important kind of triazine derivatives , is a new rubber antioxidant, also known as TAPDT or DURAZONE37. Anti-aging agent TMPPD is a new type of green and non-polluting anti-aging agent. It is mainly used to protect unsaturated artificial rubber and elastomers from aging and cracking effects of oxygen and ozone. It has super strong static ozone protection function and excellent dynamic resistance. Agin...

Claims

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Application Information

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IPC IPC(8): C07D251/70
CPCC07D251/70
Inventor 陈新民李春生向忠航
Owner JIANGSU SINORGCHEM TECH CO LTD
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