A kind of azole sulfur (selenium) ketone derivative and its preparation method and application
A technology for azole thione and derivatives, which is applied in the field of preparation of azole thione derivatives, and can solve problems such as poor compatibility of functional groups, destruction of functional groups, unfavorable preparation of azole thione functional molecules, etc.
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Embodiment 1
[0040] Preparation of 2-fluoro-2-(3-methyl-2-thio-2,3-dihydro-1H-benzo[d]imidazol-1-yl) ethyl acetate compound (R 1 is methyl, R 2 for hydrogen):
[0041]
[0042] Method 1: Add 1-methylbenzimidazole (0.4 mmol), sulfur powder (S 8 ) (0.8mmol), ethyl bromofluoroacetate (1.0mmol), in Na 2 S 2 o 4 (0.8 mmol) as a catalyst in a solution of 1,2-dichloroethane (DCE) (2.0 mL) and stirred at 80°C for 24 hours. After the reaction was completed, the reaction mixture was cooled to room temperature and the mixture was extracted with dichloromethane, and the combined organic layers were washed over anhydrous Na 2 SO 4 Dry and evaporate the solvent in vacuo on a rotary evaporator. Using 300-400 mesh silica gel to carry out flash column chromatography, the crude mixture was purified by preparative TLC monitoring spot plate at (petroleum (PE):ethyl acetate (EA)=3:1) to obtain light yellow solid product (I-1 ), m.p.: 82.4~84.0°C, the yield is 92%.
[0043] Method two: the differenc...
Embodiment 2
[0047] 2-fluoro-2-(3-methyl-2-thio-2,3-dihydro-1H-imidazol-1-yl) ethyl acetate compound (R 1 is benzyl, R 2 for hydrogen):
[0048]
[0049] Add 1-benzylbenzimidazole (0.4 mmol), sulfur powder (S 8 ) (0.8mmol), ethyl bromofluoroacetate (1.0mmol), in Na 2 S 2 o 4 (0.8 mmol) as a catalyst in a solution of 1,2-dichloroethane (DCE) (2.0 mL) and stirred at 80°C for 24 hours. After the reaction was completed, the reaction mixture was cooled to room temperature and the mixture was extracted with dichloromethane, and the combined organic layers were washed over anhydrous Na 2 SO 4 Dry and evaporate the solvent in vacuo on a rotary evaporator. Using 300-400 mesh silica gel for flash column chromatography, the crude mixture was purified by preparative TLC monitoring spot plate at (petroleum (PE):ethyl acetate (EA)=6:1) to give the product (I-20) as a white solid , m.p.: 140.2~141.2°C, the yield is 96%.
[0050] Method two: the difference with method one is that the amount of...
Embodiment 3
[0052] 1-benzyl-3-methyl-1,3-dihydro-2H-benzo[d]imidazole-2-thione compound (R 1 is methyl, R 2 for hydrogen, R 3 for benzyl):
[0053]
[0054] Method 1: Add 1-methylbenzimidazole (0.4 mmol), sulfur powder (S 8 ) (0.8mmol), benzyl bromide (1.0mmol), in Na 2 S 2 o 4 (0.8 mmol) as a catalyst in a solution of 1,2-dichloroethane (DCE) (2.0 mL) and stirred at 80°C for 24 hours. After the reaction was completed, the reaction mixture was cooled to room temperature and the mixture was extracted with dichloromethane, and the combined organic layers were washed over anhydrous Na 2 SO 4 Dry and evaporate the solvent in vacuo on a rotary evaporator. Using 300-400 mesh silica gel for flash column chromatography, the crude mixture was purified by preparative TLC monitoring spot plate at (petroleum (PE):ethyl acetate (EA)=6:1) to give the product (I-31) as a white solid , m.p.: 134.0~135.0°C, the yield is 32%.
[0055] Method 2: The difference from method 1 is that the reaction...
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