Multi-step continuous preparation method of (1alpha, 3alpha and 5alpha)-1,3,5-cyclohexane tricarbonitrile

A technology of cyclohexanetriamide and triethylamine, which is applied in the field of preparation of -1,3,5-cyclohexanetrinitrile, can solve the problems of many wastes, complicated operation and low yield

Inactive Publication Date: 2019-03-22
SHANGHAI VASTPRO TECH DEV CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0010] The technical problem to be solved by the present invention is that the preparation method of existing (1α, 3α, 5α)-1,3,5-cyclohexanetrinitrile has defects such as complicated operation, low yield and many wastes. Therefore, the present invention provides A multi-step continuous preparation method of (1α, 3α, 5α)-1,3,5-cyclohexanetrinitrile

Method used

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  • Multi-step continuous preparation method of (1alpha, 3alpha and 5alpha)-1,3,5-cyclohexane tricarbonitrile
  • Multi-step continuous preparation method of (1alpha, 3alpha and 5alpha)-1,3,5-cyclohexane tricarbonitrile
  • Multi-step continuous preparation method of (1alpha, 3alpha and 5alpha)-1,3,5-cyclohexane tricarbonitrile

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Embodiment 1

[0075] (1) Add the reaction solvent 1,2-dichloroethane (4.0eq, calculated based on 1.0eq of cis trimesic acid, the equivalents in the examples are the same) into the dry reaction flask, and then add 20.0g of raw materials cis trimesic acid (compound 1, 1.0eq) and 0.3g catalyst DMF (0.05eq), magnetically stirred. The internal temperature of the system was heated to 65 degrees, and thionyl chloride (3.3 eq) was added dropwise, and the dropping temperature was controlled at 65-70 degrees. After the dropwise addition, keep the temperature at 65-70°C for 3 hours. After the reaction is complete, steam at 75-85°C under normal pressure to collect 1,2-dichloroethane (2eq, steam out half of the amount of 1,2-dichloro Ethane is used for subsequent batches, and the system is cooled to room temperature for the next reaction.

[0076] (2) The reaction solution of step (1) is cooled to 20 degrees of internal temperature, and the mixed solution of triethylamine (3.6eq) and phenol (3.3eq) i...

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Abstract

The invention discloses a multi-step continuous preparation method of (1alpha, 3alpha and 5alpha)-1,3,5-cyclohexane tricarbonitrile. The invention provides the multi-step continuous preparation methodof the (1alpha, 3alpha and 5alpha)-1,3,5-cyclohexane tricarbonitrile, and the method comprises the following steps that (1) in a solvent, in the presence of an organic base, a compound 2 is subjectedto an esterification reaction with phenol to obtain reaction liquid containing a compound 3; and (2) the reaction liquid containing the compound 3 obtained in step (1) is subjected to an aminolysis reaction with ammonia gas to obtain a compound 4, so as to obtain the (1alpha, 3alpha and 5alpha)-1,3,5-cyclohexane tricarbonitrile. The method has the advantages of low-cost raw materials, simple andconvenient operation, high reaction yield, good product quality, few by-products, omitted post-treatment, great reduction of three wastes generated and the like, and is suitable for industrial production.

Description

technical field [0001] The invention relates to a multi-step continuous preparation method of (1α, 3α, 5α)-1,3,5-cyclohexanetrinitrile. Background technique [0002] Cyclohexane skeleton derivatives with symmetrical three substitutions are widely used in biomaterials due to their special structures and biological activities. For example, cyclohexane skeletons based on transmembrane ionophores have relatively low anion affinity. Low, with potential biological activity, can be used for the treatment of channelopathies such as cystic fibrosis; its structure is mainly that the active group is installed on the cyclohexane-basic skeleton, where (1α,3α,5α)-1,3, 5-cyclohexanetrinitrile is an important intermediate for the synthesis of the basic skeleton. [0003] For the synthesis technology of (1α,3α,5α)-1,3,5-cyclohexanetrinitrile, there are the following reports in the prior art: [0004] Literature Chemische Berichte (1995), 128, (7), 719-23 and Journal of the Chinese Chemical...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C51/60C07C61/08C07C67/14C07C69/75C07C253/20C07C255/46C07C231/02C07C233/58
CPCC07B2200/07C07C51/60C07C67/14C07C231/02C07C253/20C07C2601/14C07C61/08C07C69/75C07C255/46C07C233/58
Inventor 赖亮李金华朱文峰
Owner SHANGHAI VASTPRO TECH DEV CO LTD
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