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Method for preparing thiotrifluoroacetamide compound

A technology for thiotrifluoroacetamide and compounds, which is applied in the field of preparing thiotrifluoroacetamide compounds, can solve the problem of difficult synthesis of trifluoromethyl-containing thioamide compounds and difficult preparation of trifluoromethyl group-containing compounds Solve problems such as thioamide compounds, and achieve the effects of simple operation, easy-to-obtain products, and simple process

Pending Publication Date: 2019-05-24
WENZHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] Although there are many preparation methods of thioamide compounds at this stage, it is difficult to prepare thioamide compounds containing trifluoromethyl groups by using these methods. The group is a strong electron-withdrawing group, which makes it difficult to synthesize compounds containing trifluoromethylthioamides

Method used

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  • Method for preparing thiotrifluoroacetamide compound
  • Method for preparing thiotrifluoroacetamide compound
  • Method for preparing thiotrifluoroacetamide compound

Examples

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preparation example Construction

[0020] A method for preparing sulfur-containing trifluoroacetamide compounds, comprising the following steps: using (E)-N,1-diphenylimine as a substrate, adding elemental sulfur to the substrate, 1,1,1 -Trifluorotrichloroethane, the molar ratio of the three is 1:1:5. By adding 10% cuprous chloride, 20% 1.10-phenanthroline, 100% additive silver fluoride, 300% anhydrous potassium phosphate, 200% distilled water, in the reaction solvent of 1.4-dioxane , and reacted for 4 hours at a temperature of 120°C; the chemical reaction formula is as follows:

[0021]

[0022] The R 1 For phenyl, 4-methylphenyl, 2-methylphenyl, 4-tert-butyl, 4-biphenyl, 4-phenoxyphenyl, 4-methoxyphenyl, 4-methylthio phenyl, 4-fluorophenyl, 4-chlorophenyl, 3-chlorophenyl, 4-bromophenyl, 4-iodophenyl, 4-trifluoromethylphenyl, 4-methylformylphenyl , one of 2-naphthyl, phenethyl, and cyclopentyl;

[0023] After the reaction is finished, after cooling, the reaction solution is filtered to obtain the filtra...

specific Embodiment 1

[0024] Specific Example 1: 36.2 mg (0.2 mmol) (E)-N,1-diphenylimine, 51.2 mg (0.2 mmol) elemental sulfur, 187.0 mg (1.0 mmol) 1,1,1-trifluorotri Ethyl chloride, 2.0 mg (0.02 mmol) cuprous chloride, 7.2 mg (0.04 mmol) 1.10-phenanthroline, 25.2 mg (0.2 mmol) silver fluoride, 127.2 mg (0.6 mmol) potassium phosphate, 7.2 mg (0.4 mmol) distilled water was added to 3 mL of 1.4-dioxane solvent. Reacted at 120°C for 4 hours, cooled after the reaction, filtered, and the filtrate was rotary evaporated to remove the solvent, and the residue was subjected to silica gel column chromatography, washed with a mixed solution of petroleum ether and ethyl acetate with a volume ratio of 15:1, according to The effluent was collected by actual gradient, detected by TLC, the effluent containing the product was combined, the solvent was distilled off by a rotary evaporator, and dried in vacuo to obtain 28.3 mg of yellow oily 2,2,2-trifluoro-N-phenylthioacetamide, the yield 69%. Yellow oil. 1 H NMR...

specific Embodiment 2

[0025] Specific example two: 39.0 mg (0.2 mmol) (E)-1-phenyl-N-(4-tolyl) methyl imine, 51.2 mg (0.2 mmol) elemental sulfur, 187.0 mg (1.0 mmol) 1, 1,1-Trifluorotrichloroethane, 2.0 mg (0.02 mmol) cuprous chloride, 7.2 mg (0.04 mmol) 1.10-phenanthroline, 25.2 mg (0.2 mmol) silver fluoride, 127.2 mg (0.6 mmol) Potassium phosphate, 7.2 mg (0.4 mmol) of distilled water, was added to 3 mL of 1.4-dioxane solvent. Reacted at 120°C for 4 hours, cooled after the reaction, filtered, and the filtrate was rotary evaporated to remove the solvent, and the residue was subjected to silica gel column chromatography, washed with a mixed solution of petroleum ether and ethyl acetate with a volume ratio of 15:1, according to The effluent was collected in the actual gradient, detected by TLC, the effluent containing the product was combined, the solvent was distilled off by a rotary evaporator, and the yellow solid was obtained by vacuum drying, 26.3 mg of 2,2,2-trifluoro-N-(4-tolyl)thio Acetamid...

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Abstract

The invention discloses a method for preparing a thiotrifluoroacetamide compound, which comprises the following steps: using (E)-N, 1-N-diphenylimine as a substrate, adding equivalent elemental sulfurinto the substrate, 1.5 equivalents of 1.1.1-trifluorotrichloroethane, adding a catalyst, a ligand, an additive, alkali and distilled water, and stirring and reacting for 4 hours at the normal pressure of 120 DEG C in a reaction solvent; after the reaction is finished, filtering the reaction liquid to obtain filtrate; concentrating the filtrate, removing the solvent by using a rotating evaporatorto obtain residues, carrying out chromatography with silica gel column, eluting with an eluent, and collecting effluent according to actual gradient; combining the effluent containing the product, concentrating the combined effluent to remove the solvent, and finally drying in vacuum to obtain a target product. The method has the advantages of simple preparation process, less pollution, low energy consumption and high yield.

Description

technical field [0001] The invention relates to the technical field of thioamide compounds, in particular to a method for preparing thiotrifluoroacetamide compounds. Background technique [0002] Thioamide compounds are a class of compounds that exist in nature. Thioamide compounds are also a class of important biologically active molecules that have significant biological and pharmacological effects, including antibacterial and inhibitory effects. For example, the natural product Closthioamide has antibacterial properties; the DNA gyrase inhibitor hydroxymethylthiolactam cyclothiazil belongs to thioamide compounds; Ncyclohexylethyl-ETAsV is a peptidomimetic inhibitor. Therefore, chemists have developed various methods for constructing thioamides. [0003] When chemists construct thiotrifluoroacetamide compounds, the most direct method is to use trifluoromethylacetamide as a raw material and use Lawson's reagent as a sulfur source to perform a vulcanization reaction to gene...

Claims

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Application Information

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IPC IPC(8): C07C327/42
Inventor 张兴国宋祎康张小红胡伯伦邓辰亮
Owner WENZHOU UNIVERSITY
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