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Preparation method of 2-hydroxy-2-arylthioacetamide

A technology of arylthioacetamide and hydroxythioamide, which is applied in the field of organic compound synthesis, can solve the problems of complicated operation, harsh conditions, high price and the like, and achieves the effects of simple experimental operation, mild reaction conditions and convenient handling.

Inactive Publication Date: 2012-09-05
SUZHOU UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The commonly used vulcanization reagent is phosphorus pentasulfide, or its aromatic hydrocarbon derivatives, called Laweson reagent. The disadvantage of this method is that a large amount of waste water is produced in the manufacture of this type of vulcanization reagent, and the price is expensive. Although sulfur occupies a certain proportion in this reagent, it cannot It is completely utilized, and phosphorus and sulfur salts are formed during the reaction process and enter the water phase. According to calculations, 50 tons of phosphorus and sulfur-containing wastewater will be discharged to produce 1 ton of products, which will cause great harm to the environment.
[0006] The method reported in the above literature is cumbersome to operate, post-treatment is difficult, the selectivity of product formation is poor, accompanied by by-products, the yield is low, the conditions are harsh and sulfur-containing reagents are used , bad smell, easy to pollute the environment

Method used

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  • Preparation method of 2-hydroxy-2-arylthioacetamide
  • Preparation method of 2-hydroxy-2-arylthioacetamide
  • Preparation method of 2-hydroxy-2-arylthioacetamide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] 1. Add zinc powder (0.78 g, 12 mmol) and 20 mL of anhydrous THF to a 100 mL three-necked flask, under nitrogen protection, stir at room temperature, and slowly inject TiCl 4 (0.7 mL, 6 mmol), the mixture was refluxed for 2 h, and cooled to room temperature to obtain a low-valent titanium reagent in black paste, slowly adding a solution of 2-carbonylthioamide (2 mmol) dissolved in 10 mL THF, and the addition was completed. React at room temperature for 5-10 min, and TLC detects that the reaction is complete.

[0029] 2. After the reaction, decompose with 100 mL of 3% hydrochloric acid, and then extract with chloroform (3×50 mL). The organic layers were combined, washed with water until neutral (2×50 mL), dried over anhydrous sodium sulfate, filtered to remove the desiccant, and evaporated to remove the solvent under reduced pressure to obtain a crude product, which was recrystallized from ethanol with a yield of 91%. The reaction equation is expressed as follows:

[00...

Embodiment 2

[0032] 1. Add zinc powder (0.78 g, 12 mmol) and 20 mL of anhydrous THF to a 100 mL three-necked flask, under nitrogen protection, stir at room temperature, and slowly inject TiCl 4 (0.7 mL, 6 mmol), the mixture was refluxed for 2 h, cooled to room temperature to obtain low-valent titanium reagent in black paste, slowly added 2-carbonylthioamide (2 mmol) dissolved in 10 mL THF solution, added complete. React at room temperature for 5-10 min, and TLC detects that the reaction is complete.

[0033] 2. After the reaction, decompose with 100 mL of 3% hydrochloric acid, and then extract with chloroform (3×50 mL). The organic layers were combined, washed with water until neutral (2×50 mL), dried over anhydrous sodium sulfate, filtered to remove the desiccant, and evaporated to remove the solvent under reduced pressure to obtain a crude product, which was recrystallized from ethanol with a yield of 89%. The reaction equation is expressed as follows:

[0034]

Embodiment 3

[0036] 1. Add zinc powder (0.78 g, 12 mmol) and 20 mL of anhydrous THF to a 100 mL three-necked flask, under nitrogen protection, stir at room temperature, and slowly inject TiCl 4 (0.7 mL, 6 mmol), the mixture was refluxed for 2 h, cooled to room temperature to obtain low-valent titanium reagent in black paste, slowly added 2-carbonylthioamide (2 mmol) dissolved in 10 mL THF solution, added complete. React at room temperature for 5-10 minutes, and TLC detects that the reaction is complete.

[0037] 2. After the reaction, decompose with 100 mL of 3% hydrochloric acid, and then extract with chloroform (3×50 mL). The organic layers were combined, washed with water until neutral (2×50 mL), dried with anhydrous sodium sulfate, filtered to remove the desiccant, and evaporated to remove the solvent under reduced pressure to obtain a crude product, which was subjected to silica gel column chromatography [eluent V (acetone): V (petroleum ether) = 1:3] to isolate the product with a y...

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Abstract

The invention discloses a preparation method of 2-hydroxy-2-arylthioacetamide, which comprises the following steps: adding zinc powder and anhydrous THF (tetrahydrofuran) into a three-necked flask, and stirring at room temperature in a nitrogen atmosphere; slowly injecting TiCl4, refluxing the mixture for 2 hours, and cooling to room temperature to obtain the black pasty low-price tiron; slowly adding 2-carbonylthioamide, dissolving the 2-carbonylthioamide in the THF solution, and finishing adding; reacting at room temperature for 5-10 minutes, and detecting whether the reaction is completed by TLC (thin layer chromatography); after the reaction finishes, decomposing with 3% hydrochloride, and extracting with chloroform; merging the organic layers, washing with water to neutral state, drying with anhydrous sodium sulfate, filtering out the desiccant, and distilling under reduced pressure to remove the solvent, thereby obtaining the crude product; and purifying the crude product to obtain the target product 2-hydroxythioamide. Compared with the existing traditional reduction methods, the method disclosed by the invention has many advantages, and the biggest characteristics are mild reaction conditions and short time; and the experiment is simple to operate and convenient for treatment, and the yield is up to more than 80%.

Description

[0001] technical field [0002] The invention belongs to the synthesis of organic compounds and relates to the synthesis of 2 - Carbonylthioamide reduction to 2 - A method for hydroxythioamide, in particular to a preparation method for 2-hydroxyl-2-arylthioacetamide. Background technique [0003] Thioamides are a class of important carboxylic acid derivatives with important biological and pharmaceutical activities; at the same time, as a class of multifunctional organic synthesis intermediates, they have been widely used in the fields of organic synthetic chemistry, pharmaceutical synthetic chemistry, and material chemistry. Applications. Thioamides have been widely reported in the screening of antibacterial drugs, and have plant protection properties in the field of agriculture, and may be beneficial to control or prevent pathogenic microorganisms, especially fungi, that harm plants. [0004] There are many methods for synthesizing thioamides, and the most directly conce...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C327/44C07D295/14
Inventor 史达清孙芳
Owner SUZHOU UNIV
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