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Chemical synthesis method of 3-isoxazolyl benzyl acetate

A technology of isoxazolyl and benzyl acetate, which is applied in the field of chemical synthesis of 3-isoxazolyl benzyl acetate, can solve problems such as difficulty in obtaining, unfavorable production, and high production cost requirements, and achieve the effect of guaranteed yield

Inactive Publication Date: 2019-01-22
盐城锦明药业有限公司 +1
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The existing synthetic methods are difficult to obtain raw materials, and at the same time require high production costs, which is not conducive to production

Method used

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  • Chemical synthesis method of 3-isoxazolyl benzyl acetate

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preparation example Construction

[0017] refer to figure 1 , a chemical synthesis method of 3-isoxazolyl benzyl acetate, comprising the following steps:

[0018] S1: Addition reaction of butenenitrile and bromine gas to generate 3-amino-5-methylisoxazole under the action of derivatives of hydroxylamine;

[0019] S2: Then 3-amino-5-methylisoxazole and 3-amino-5-methylisoxazole are catalyzed to produce diazonium salt at low temperature, and the diazonium salt is subjected to a substitution reaction under hydrochloric acid environment to replace the amino group to produce 3, 5-Dimethylisoxazole, demethylated to produce 3-chloromethylisoxazole;

[0020] S3: Add 3-chloromethylisoxazole and cuprous cyanide to an organic solvent, the organic solvent is dimethyl sulfoxide, and react to prepare 3-isoxazole acetonitrile;

[0021] S4: Add 3-isoxazole acetonitrile to hydrochloric acid, and hydrolyze to obtain 3-isoxazole acetic acid;

[0022] S5: Add 3-isoxazoleacetic acid and benzyl alcohol into dichloromethane or tri...

Embodiment 1

[0024] Embodiment 1: 3-chloromethyl isoxazole synthesis:

[0025] Using chloroacetyl chloride and acetylene gas as raw materials, anhydrous aluminum trichloride as a catalyst, and methylene chloride as a solvent to obtain 1,4-dichloro-3-butene-2-one; then 1,4-dichloro - 3-buten-2-one and hydroxylamine hydrochloride are refluxed and closed in methanol solvent to obtain 3-chloromethylisoxazole, and the specific steps for synthesizing 1,4-dichloro-3-buten-2-one are 110g , chloroacetyl chloride with a molar mass of 1.06 was slowly added dropwise to 150 g of anhydrous AlCl with a molar mass of 1.17 3 and 300ml of CH 2 Cl 2 In the mixed solution, the mixture was cooled to -5°C, acetylene gas was introduced for 2 hours, the reactant was slowly poured into ice water, the organic layer was washed with cold water, dried over anhydrous sodium sulfate, and collected under reduced pressure at 78-83°C / 16mmHg Distillate oil 64g of 2,4-dichloro-2-buten-2-one, the specific steps of synthesi...

Embodiment 2

[0032] Embodiment 2: Synthesis of 3-chloromethylisoxazole

[0033] Use acetylacetonate and hydroxylamine to generate 5-methylisoxazole-3-carboxylate, then perform nucleophilic addition with ammonia to generate 5-methylisoxazole-3-carboxamide, and then dealcoholize The product 3-amino-5-methylisoxazole is produced, and then 3-amino-5-methylisoxazole is catalyzed to make diazonium salt at low temperature, and the diazonium salt is prepared under hydrochloric acid environment A substitution reaction occurs, and the amino group is substituted to produce 3,5-dimethylisoxazole, and demethylated to produce 3-chloromethylisoxazole.

[0034] Add dimethyl sulfoxide and 3-chloromethylisoxazole into the three-necked flask, add cuprous cyanide, heat to 30°C, after the reaction is complete, add water, extract the combined organic phase with dichloromethane, and wash with saturated bicarbonate Wash with sodium, wash with saturated brine, dry over anhydrous sodium sulfate, and concentrate to...

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Abstract

The invention discloses a chemical synthesis method of 3-isoxazolyl benzyl acetate. The chemical synthesis method comprises the following steps: S1, carrying out addition reaction through butene nitrile and bromine gas and generating 3-amino-5-methylisoxazole in the presence of a hydroxylamine derivative; S2, preparing 3-amino-5-methylisoxazole into diazonium salt under low temperature under the action of catalysis, carrying out substitution reaction on the diazonium salt in a hydrochloric acid environment, substituting amino and preparing 3,5-dimethylisooxazole, carrying out demethylation andpreparing 3-chloromethylisoxazole; and S3, adding 3-chloromethylisoxazole and cuprous cyanide into an organic solvent which is dimethyl sulfoxide, reacting and preparing 3-isooxazole acetonitrile. According to the chemical synthesis method of 3-isoxazolyl benzyl acetate, the raw materials are products obtained by directly cracking petroleum; production is carried out by five steps of addition, catalysis, substitution, hydrolysis and esterification; the reaction is rapid; when 3-chloromethylisoxazole as an intermediate is prepared, the yield reaches up to 75%; the production yield is ensured.

Description

technical field [0001] The invention relates to the technical field of chemical synthesis, in particular to a chemical synthesis method of 3-isoxazolyl benzyl acetate. Background technique [0002] 3-Isoxazolyl benzyl acetate, as an isoxazole derivative, has a wide range of pharmacological activities after structural derivation, and is effective in antibacterial, antiviral, treatment or prevention of various bone diseases, antidepressant activity and anxiolytic activity There are applications in all aspects. The existing synthesis method is difficult to obtain raw materials, and the production cost is relatively high, which is not conducive to production. Contents of the invention [0003] Based on the technical problems existing in the background technology, the present invention proposes a chemical synthesis method of 3-isoxazolyl benzyl acetate. [0004] A kind of chemical synthesis method of 3-isoxazolyl benzyl acetate proposed by the present invention comprises the ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D261/08
CPCC07D261/08
Inventor 吴振冯雪馨房忠雪杨锦明胡志伟詹浩晟
Owner 盐城锦明药业有限公司
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