1,2,3-thiadiazole-containing sulfilimine (sulfonimine) compounds and their preparation method and use
A technology of thiadiazoles and compounds, applied in the field of sulfimide and sulfoximine compounds
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Embodiment 1
[0055] Embodiment 1: Preparation of starting material 4-(1-bromoethyl)-1,2,3-thiadiazole-5-ethyl carboxylate If:
[0056]
[0057] 30 ml of absolute ethanol, ethyl propionoacetate (7.0 g, 48.5 mmol), and hydrazinomethylcarbonate (4.4 g, 48.5 mmol) were successively added to a 100 ml three-neck round bottom flask, and stirred at room temperature for 24 hours. Concentrated under reduced pressure to remove the solvent to obtain 11.2 g of a colorless viscous product with a yield of 93%, and the product was directly used in the next reaction;
[0058] Under the protection of nitrogen, the above-mentioned prepared compound (10.0 g, 46.2 mmol) and 20 ml of dried dichloromethane were successively added to a 100 ml three-neck round bottom flask, cooled to 0 degrees Celsius in an ice-water bath, and slowly added dropwise with thionyl chloride ( 10.3 ml, 138.7 mmol), after the dropwise addition, the reaction solution was stirred at room temperature for 24 hours. The reaction system w...
Embodiment 2
[0060] Embodiment 2: the preparation of raw material 4-(1-chloroethyl)-1,2,3-thiadiazole Ih:
[0061] Add metal magnesium (30 mmol), ether (20 milliliters), and catalytic amount of iodine in a 100 milliliter three-necked round-bottomed flask, slowly add a solution of methyl iodide (20 millimoles) in ether (20 milliliters) dropwise in an ice-water bath, drop After the addition was complete, stir at 0°C for 2 hours. A solution of 1,2,3-thiadiazole-4-carbaldehyde (2.28 g, 20 mmol) in diethyl ether (20 ml) was slowly added dropwise in an ice-water bath. After the addition was complete, the mixture was stirred at room temperature for 2 hours. After the reaction was completed, slowly add ice water dropwise in an ice-water bath to quench the reaction, extract the aqueous phase with ether (20 ml × 3), combine the organic phases, wash the organic layer twice with water and saturated brine, and dry the organic layer over anhydrous magnesium sulfate , the solvent was removed under reduc...
Embodiment 3
[0063] Embodiment 3: Preparation of starting material 4-(1-chloroethyl)-5-methyl-1,2,3-thiadiazole Ii:
[0064]Add metal magnesium (30 mmol), ether (20 milliliters), and catalytic amount of iodine in a 100 milliliter three-necked round-bottomed flask, slowly add a solution of methyl iodide (20 millimoles) in ether (20 milliliters) dropwise in an ice-water bath, drop After the addition was complete, stir at 0°C for 2 hours. Slowly add a solution of 5-methyl-1,2,3-thiadiazole-4-carbaldehyde (2.56 g, 20 mmol) in ether (20 ml) dropwise in an ice-water bath, after the addition is complete, stir at room temperature for 2 hours; After completion, ice water was slowly added dropwise in an ice-water bath to quench the reaction, the aqueous phase was extracted with ether (20 ml × 3), the organic phases were combined, the organic layer was washed twice with water and saturated brine, and the organic layer was dried over anhydrous magnesium sulfate. The solvent was removed under reduced ...
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