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Preparation method of beta-hydroxyl substituted alkyl dithiocarbamate

A technology of alkyl dithiocarbamate and hydroxyl group, applied in the field of organic synthesis, can solve problems such as lack of methods, and achieve the effects of simple process, wide application range and mild reaction conditions

Active Publication Date: 2021-10-08
HENAN AGRICULTURAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The main reason may be due to the lack of effective methods

Method used

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  • Preparation method of beta-hydroxyl substituted alkyl dithiocarbamate

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Embodiment 1

[0024] The preparation method of 2-(4-chlorophenyl)-2-hydroxyethyl dimethyl amino dithioate comprises the following steps:

[0025] (1) Take 0.2 mmol of 4-chlorostyrene, 0.1 mmol of tetramethylthiuram disulfide and 0.2 mmol of sodium ethoxide, add 1 ml of 1.4-dioxane to obtain a mixture, and place the mixture in a 5 ml Schlenk tube , heated in an oil bath at 80°C, reacted for 48 hours, and cooled to room temperature to obtain a reaction solution;

[0026] (2) The reaction solution obtained in step (1) is directly concentrated to obtain a concentrate, and the concentrate is separated by thin-layer chromatography using ethyl acetate / petroleum ether=1 / 5 (v / v) as a developing solvent to obtain 24.2 mg of target product.

[0027] The target product yield of the present embodiment is 88%.

[0028] NMR characterization of the target product is as follows: 1H NMR (400 MHz, CDCl3) ppm: 7.46-7.39(d, J = 8.4 Hz, 2H), 7.36-7.31 (d, J = 8.5 Hz, 2H), 5.09-4.98 (d, J = 8.4 Hz, 1H), 3.90-3...

Embodiment 2

[0030] The preparation method of 2-(3-chlorophenyl)-2-hydroxyethyl dimethyl amino dithioate comprises the following steps:

[0031] (1) Take 0.2mmol of 3-chlorostyrene, 0.1mmol of tetramethylthiuram disulfide and 0.2mmol of sodium ethoxide, add 1ml of 1.4-dioxane to obtain a mixture, and place the mixture in a 5ml Schlenk tube , heated in an oil bath at 80°C, reacted for 48 hours, and cooled to room temperature to obtain a reaction solution;

[0032] (2) The reaction solution obtained in step (1) is directly concentrated to obtain a concentrate, and the concentrate is separated by thin-layer chromatography using ethyl acetate / petroleum ether=1 / 5 (v / v) as a developing solvent to obtain 17.1 mg of target product.

[0033] The target product yield of the present embodiment is 62%.

[0034] NMR characterization of the target product is as follows: 1H NMR (400 MHz, CDCl3) ppm: 7.49 (s,1H), 7.39-7.34 (d, J = 7.3 Hz, 1H), 7.34-7.29 (d, J = 7.8 Hz , 1H), 7.29-7.24(m, 1H), 5.08-4.98...

Embodiment 3

[0036] The preparation method of 2-(4-bromophenyl)-2-hydroxyethyl dimethyl amino dithioate comprises the following steps:

[0037] (1) Take 0.4mmol of 4-bromostyrene, 0.2mmol of tetramethylthiuram disulfide and 0.4mmol of sodium ethoxide, add 1ml of 1.4-dioxane to obtain a mixture, and place the mixture in a 5ml Schlenk tube , heated in an oil bath at 80°C, reacted for 48 hours, and cooled to room temperature to obtain a reaction solution;

[0038] (2) The reaction solution obtained in step (1) is directly concentrated to obtain a concentrate, and the concentrate is separated by thin-layer chromatography using ethyl acetate / petroleum ether=1 / 5 (v / v) as a developing solvent to obtain 26.7 mg of target product.

[0039] The target product yield of the present embodiment is 84%.

[0040]NMR characterization of the target product is as follows: 1H NMR (400 MHz, CDCl3) ppm: 7.54-7.45(d, J = 8.4 Hz, 2H), 7.41-7.32 (d, J = 8.3 Hz, 2H), 5.10-4.96 (dd, J = 8.4,3.0 Hz, 1H), 3.90-3.79...

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Abstract

The invention provides a preparation method of beta-hydroxyl substituted alkyl dithiocarbamate, and belongs to the technical field of organic synthesis. The preparation method comprises the following steps: (1) adding an alkali catalyst, a styrene derivative and thiuram disulfide into an organic solvent, carrying out a reaction, and then cooling to room temperature to obtain a reaction solution; and (2) concentrating, separating and purifying the reaction solution obtained in the step (1) to obtain the product. According to the invention, a one-pot boiling method is adopted, alkali is used as a catalyst, a styrene derivative and thiuram disulfide which are economical and easy to obtain are used as raw materials, a coupling reaction is directly carried out in air to generate a corresponding beta-hydroxyl substituted dithiocarbamate compound, and the product can be used as an antibacterial agent, an anti-cancer agent, a vulcanization accelerator and the like; and the synthesis system is wide in application range, compatible with functional groups such as halogenation, alkyl and alkoxy, simple in process, convenient to operate, mild in reaction condition, wide in substrate range, high in yield and suitable for popularization and application.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a preparation method of β-hydroxyl substituted alkyl dithiocarbamate. Background technique [0002] In the past decade, transition metal-catalyzed difunctionalization of alkenes has been an effective method to introduce two functional groups into alkenes through a one-step reaction, which has the advantages of high efficiency, good regioselectivity and stereoselectivity, and strong tolerance to functional groups. . However, the use of transition metals can cause potential contamination of products, which is especially important in the pharmaceutical industry. [0003] In response to the above technical problems, in recent years, a transition metal-free synthesis method has been proposed. Transition-metal-free synthetic approach Although numerous synthetic results have been obtained for the selective difunctionalization of alkenes, the synthesis of β-hydroxyl-substitut...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C333/14C07D277/26
CPCC07C333/20C07D277/26
Inventor 武志勇赵铭钦来苗郝帅
Owner HENAN AGRICULTURAL UNIVERSITY