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A kind of preparation method of chlorinated acetine

A kind of chlorinated dimethalin, equivalent technology, applied in the field of medicine, can solve the problems of low total yield, low efficiency, poor water solubility, etc., and achieve the effect of simple synthesis route

Inactive Publication Date: 2021-07-02
YUNNAN MINZU UNIV
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  • Description
  • Claims
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Problems solved by technology

The total yield is between 0.003% and 0.07%. Due to its poor water solubility, the efficiency of large-scale industrial extraction and production is low and the cost is high, and the total yield obtained by its total synthesis is not high

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  • A kind of preparation method of chlorinated acetine

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[0011] The preparation method of the chlorinated dimethicone of the present invention uses azabenzobornene and 4,5-dimethoxy-2-(methoxycarbonyl)phenylboronic acid as reaction raw materials, and undergoes a simple five-step reaction. The synthesis obtains chlorinated acetine, and its synthetic route is as follows:

[0012] .

[0013] The preparation method of described chlorinated acetine comprises the following steps:

[0014] 1) Azabenzobornene and 4,5-dimethoxy-2-(methoxycarbonyl)phenylboronic acid are used as raw materials for the reaction, and palladium acetate is used as the catalyst to obtain intermediate 1;

[0015] 2) Dissolving intermediate 1 in an organic solvent and adding trifluoroacetic acid or trifluoromethanesulfonic acid to react to obtain intermediate 2;

[0016] 3) Reaction of intermediate 2 with methyl iodide to obtain intermediate 3;

[0017] 4) Intermediate 4 is obtained by oxidation of intermediate 3;

[0018] 5) The intermediate 4 was reduced and d...

Embodiment 1

[0027] 1) Synthesis of intermediate 1

[0028] Azabenzobornene (1 eq.) and 4,5- Dimethoxy-2-(methoxycarbonyl)phenylboronic acid (2-4 equivalents) was reacted at room temperature for 1 hour, and the reaction solution was detected by TLC. The solvent was evaporated to dryness under reduced pressure, and the residue was subjected to silica gel column chromatography to obtain Intermediate 1, a white solid, with a yield of 90%. 1 H NMR (400 MHz, CDCl 3 ) δ 7.22 (s, 1H), 7.13 (s, 1H), 6.72 (s, 1H), 6.65 (s, 1H), 6.55 (t, J = 9.2 Hz, 1H), 6.02 (dd, J = 9.6, 4.8 Hz, 1H), 5.92(d, J = 8.5 Hz, 2H), 5.18 (dd, J = 9.6, 7.6 Hz, 1H), 4.53 (d, J = 10.1 Hz,1H), 3.93 (s, 3H), 3.84 - 3.74 (m, 1H), 3.70 (s, 3H), 3.65 (s, 3H), 1.38 (s,9H). 13 C NMR (CDCl 3 , 100 MHz): δ 168.1, 155.3, 147.3, 146.9, 137.8, 129.1,128.5, 128.4, 128.1, 127.4, 127.2, 107.1, 101.0, 79.4, 60.4, 56.1, 55.7,52.4, 51.5, 44.8, 28.4, 21.1, 14.2.

[0029] 2) Synthesis of Intermediate 2

[0030] Dissolve Intermedi...

Embodiment 2

[0038] Repeat the method of embodiment 1, just make following modification:

[0039] 1 Change the chloroform in steps 3 and 4 to dichloromethane;

[0040] 2 Quench the reaction with wet tetrahydrofuran in step 5;

[0041] The product total yield that this implementation makes is 70%.

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Abstract

The invention discloses a preparation method of chlorinated dimethicone, comprising the following steps: 1) using metal palladium / ligand to catalyze 4,5-dimethoxy-2-(methoxycarbonyl)phenylboronic acid and aza Benzobornene reaction to obtain intermediate 1; 2) Dissolving intermediate 1 in an organic solvent and then adding trifluoroacetic acid to react at room temperature to obtain intermediate 2; 3) Intermediate 2 is methylated, oxidized, reduced, and treated with hydrochloric acid Obtained dihedral chloride. The synthesis route of the method of the present invention is relatively simple, and the total synthesis yield of the chlorinated dimethalin is as high as more than 72%.

Description

technical field [0001] The invention belongs to the technical field of medicines, and in particular relates to a preparation method of amphetine chloride. Background technique [0002] LMZ is a plant of the genus Zanthoxylum Rutaceae, which is mainly distributed in southern provinces such as Guangxi, Yunnan, Guangdong, and Fujian in my country. Nitidine is an extract of the dried roots of traditional Chinese medicine LMZ, which has various physiological activities such as promoting blood circulation, relieving pain, anti-inflammatory and anti-tumor, and can be used to treat bruises, snake bites, toothache, lymphadenitis, malaria and tumors and many other diseases. [0003] [0004] double-sided needle base [0005] At present, chlorinated cinnamon is mainly extracted and separated from different plants of the genus Zanthoxylum, and the methods used to extract alkaloids are also applicable to chlorinated chlorinated, mainly including reflux method, enzymatic method, ultr...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D491/056
Inventor 周永云樊保敏陈景超樊瑞峰孙蔚青曾广智尹俊林林成源李思达
Owner YUNNAN MINZU UNIV
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