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Novel method for preparing benzo 1,3-oxathiane-4-ketone

A technology of oxathione and a new method, which is applied in the field of preparation of benzo1,3-oxathione-4-one, can solve the problem that the yield is only 36%, the efficiency is not high, and it is irritating Problems such as smell

Active Publication Date: 2019-03-08
CHANGZHOU UNIV
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Problems solved by technology

[0003] The first method, using o-carboxythiophenol and formaldehyde as raw materials, obtains benzo1,3-oxathiolane-4-one under the action of D-type camphorsulfonic acid. The disadvantage of this method is to obtain The yield of the target product is low, the yield is only 36%, and o-carboxythiophenol and formaldehyde are used as raw materials for the reaction, which has a pungent smell and is harmful to the human body
The second method is to use 2-carboxyphenyl methyl sulfoxide as raw material to obtain the target product under the action of acetic anhydride. Since the raw material used needs to be prepared by oxidation of the corresponding 2-carboxyphenyl methyl sulfide, the reaction is not efficient

Method used

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  • Novel method for preparing benzo 1,3-oxathiane-4-ketone

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[0013] Add 2-carboxyphenyl methyl sulfide (1mmol, 0.17g), silver oxide (1mmol, 0.23g), 1-chloromethyl-4-fluoro-1,4-diazepine in sequence to a 100mL pressure tube Bicyclo[2.2.2]octane bis(tetrafluoroborate) salt (1mmol, 0.35g) and 1,2-dichloroethane (10mL) were reacted at 120°C with vigorous stirring for 10 hours. After the reaction, it was cooled to room temperature, and the reaction liquid was concentrated and separated by column chromatography in sequence to obtain benzo1,3-oxathiolane-4-one (0.12 g, 72%).

[0014] The equations involved in the reaction are as follows:

[0015]

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Abstract

The invention relates to the technical field of fine chemical engineering and discloses a novel method for preparing benzo 1,3-oxathiane-4-ketone. The method includes steps: taking 2-carboxyphenyl dimethyl sulfide as a raw material, taking silver oxide and 1-chloromethyl-4-fluoro-1,4-diazabicyclo[2.2.2]octane di(tetrafluoroboric acid) salt as additives, and subjecting to reaction in 1,2-dichloroethane at 120 DEG C for 10 hours to obtain benzo 1,3-oxathiane-4-ketone. Compared with an existing method, the novel method has advantages that quickness and simplicity are realized, commercial 2-carboxyphenyl methyl sulfide is directly used as a reaction raw material to realize one-step direct construction of a target product, and novel reaction, simplicity in operation, high efficiency, potentialindustrial values and worthiness of popularization and application are realized.

Description

technical field [0001] The invention belongs to the field of fine chemical industry and relates to a new method for preparing benzo1,3-oxathiolane-4-one. Background technique [0002] Thioether compounds, especially thioether heterocyclic skeletons, widely exist in various natural products with biological activity, pharmaceuticals and food additives, so chemists have been exploring various properties and research routes of such compounds and their derivatives. Benzo 1,3-oxathione-4-one derivatives not only have insecticidal and bactericidal activities, but also are important intermediates for the synthesis of benzisothiazolone derivatives. At present, there are two main methods for synthesizing benzo1,3-oxathione-4-one compounds in the literature: [0003] The first method, using o-carboxythiophenol and formaldehyde as raw materials, obtains benzo1,3-oxathiolane-4-one under the action of D-type camphorsulfonic acid. The disadvantage of this method is to obtain The yield of...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D327/06
CPCC07D327/06
Inventor 杨科李义李正义孙小强
Owner CHANGZHOU UNIV
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