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N-difluoromethylazole sulfur (selenium) urea derivative and preparation method thereof

A technology of difluoromethyl imidazole thiourea and difluoromethyl triazole thiourea, which is applied in the field of N-difluoromethyl azole thiourea derivatives and its preparation, and can solve the problem of functional group damage, difficulty in obtaining, unfavorable Problems such as the construction of drug molecular libraries, to achieve the effect of mild conditions

Active Publication Date: 2019-02-22
SOUTH CHINA AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, TFDA fluorine-containing reagents are not easy to obtain, and the applicability of substrates is very limited, which is not conducive to obtaining thiourea compounds with various structures; the use of strong bases also has varying degrees of damage to functional groups, resulting in poor compatibility of functional groups, which is not conducive to Construction of Drug Molecular Library

Method used

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  • N-difluoromethylazole sulfur (selenium) urea derivative and preparation method thereof
  • N-difluoromethylazole sulfur (selenium) urea derivative and preparation method thereof
  • N-difluoromethylazole sulfur (selenium) urea derivative and preparation method thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Benzyl-3-(difluoromethyl)-1,3-dihydro-2H-benzo[d]imidazole-2-thione compound shown in preparation formula I (R1 is benzyl, R 2 for hydrogen):

[0037]

[0038] The synthetic steps of 1-benzylbenzimidazole:

[0039] In an oven-dried 100 ml round flask equipped with a magnetic stirrer, add benzimidazole (5.0 mmol, 0.59 g), benzyl bromide (6.0 mmol) and Cs 2 CO 3 (10.0 mmol). The reaction mixture was stirred with acetonitrile at 80°C under reflux for 8 hours. After the reaction was completed, the reaction mixture was cooled to room temperature. Acetonitrile was removed under vacuum to give a residue which was dissolved in dichloromethane and filtered to remove inorganic salts. The filtrate was concentrated in vacuo and the resulting residue was purified by flash column chromatography using petroleum and EtOAc as eluents in 92% (0.957 g) isolated yield.

[0040] Method 1: Add 1-benzylbenzimidazole (0.4 mmol), sulfur powder (S 8 ) (0.8mmol), ethyl bromodifluoroacet...

Embodiment 2

[0043] 1-(difluoromethyl)-3-methyl-1,3-dihydro-2H-benzo[d]imidazole-2-thione compound shown in preparation formula I (R 1 is methyl, R 2 for hydrogen):

[0044]

[0045] Add 1-methylbenzimidazole (0.4 mmol), sulfur powder (S 8 ) (0.8mmol), ethyl bromodifluoroacetate (1.0mmol) in sodium hydroxymethylsulfinate (HOCH 2 SO 2 Na) (0.8 mmol) was used as a catalyst in a solution of N,N-dimethylacetamide (DMA) (2.0 mL) and the reaction was stirred at 100°C for 24 hours. After the reaction, the reaction mixture was cooled to room temperature, the mixture was extracted with saturated brine and ethyl acetate, and the combined organic layers were washed with anhydrous Na 2 SO 4 Dry and evaporate the solvent in vacuo on a rotary evaporator. The crude mixture was purified by flash column chromatography using 300-400 mesh silica gel and monitored spot plate by preparative TLC to give the product (I-10) as a white solid, m.p.: 111.3-112.5°C, yield 73%.

Embodiment 3

[0047] 1-benzyl-3-(difluoromethyl)-1,3-dihydro-2H-imidazole-2-thione compound (R 1 for benzyl):

[0048]

[0049] Add 1-benzylimidazole (0.4 mmol), sulfur powder (S 8 ) (0.8mmol), ethyl bromodifluoroacetate (1.0mmol) in sodium hydroxymethylsulfinate (HOCH 2 SO 2 Na) (0.8 mmol) was used as a catalyst in a solution of N,N-dimethylacetamide (DMA) (2.0 mL) and the reaction was stirred at 100°C for 24 hours. After the reaction, the reaction mixture was cooled to room temperature, the mixture was extracted with saturated brine and ethyl acetate, and the combined organic layers were washed with anhydrous Na 2 SO 4 Dry and evaporate the solvent in vacuo on a rotary evaporator. The crude mixture was purified by flash column chromatography using 300-400 mesh silica gel and monitored spot plate by preparative TLC to give the product (I-24) as a light yellow solid, m.p.: 107.5-108.4°C, yield 37%.

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Abstract

The invention discloses an N-difluoromethylazole sulfur (selenium) urea derivative and a preparation method thereof. The N-difluoromethylazole sulfur (selenium) urea derivative comprises N-difluoromethyl benzimidazole sulfourea, N-difluoromethyl imidazole sulfourea, N-difluoromethyl triazole sulfourea and an relevant N-difluoromethyl selenourea derivative; and a benzimidazole derivative, an imidazole derivative or a triazole derivative, elemental sulfur powder or selenium powder, and a catalyst are added into a reaction tube, an organic solvent is added into the reaction tube, halohydrocarbonis injected into the reaction tube, and reacting is carried out under a heating condition to obtain the N-difluoromethylazole sulfur (selenium) urea derivative. The preparation method is simple and easy to operate, the condition is mild, the cheap and economical effects are achieved, and the provided compounds have important potential application value in pesticides, medicines and organic functional materials.

Description

technical field [0001] The invention belongs to the technical field of organic chemical reactions, and in particular relates to an N-difluoromethylazole thio(selenium) urea derivative and a preparation method thereof. Background technique [0002] Azole compounds such as benzimidazole, imidazole, triazole and other derivatives have important applications in the field of medicine and materials, and play an important role in the creation of new and efficient drugs. Due to their high efficiency, low toxicity, excellent biological activity and various structural changes, these compounds have been widely used in pesticides and medicines, and have always been the focus and focus of organic chemistry research. (Li Yan, Organic Chemistry, 2007, 28(2): 210-217; Zhang Ying, Pesticides, 2008, 47(3), 164-170). Selective fluorination and fluoroalkylation of organic compounds lead to dramatic changes in the electronic effects and skeletal characteristics of the products. Such fluorine-c...

Claims

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Application Information

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IPC IPC(8): C07D235/28C07D233/84C07D249/12C07D471/04C07D473/34C07D405/06C07D235/24C07D233/66
CPCC07D233/84C07D235/24C07D235/28C07D249/12C07D405/06C07D471/04C07D473/34C07D233/66
Inventor 汤日元邓建超徐莉
Owner SOUTH CHINA AGRI UNIV
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