Method for preparing 3-methyl quinolines-8-sulfochlorides
A technology of methylquinoline and sulfonyl chloride, applied in the direction of organic chemistry, can solve problems such as difficult to meet the requirements, and achieve the effects of easy availability of raw materials, large-scale production, and low cost
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Embodiment 1
[0029] Add chlorosulfonic acid (233 grams, 2.0 moles) in the 500 milliliters four-neck reaction flasks with mechanical stirrer, thermometer, reflux condenser and feeding port, at 25 ℃, drop into 3-methylquinoline (143 g, 1.0 mol), and then sodium sulfate (14 g, 0.1 mol) was added. After the addition, the reaction was carried out at a constant temperature of 25° C. for 1 hour, then the temperature was raised to 120° C., and the reaction was carried out for 4 hours. The temperature was lowered to 50°C, thionyl chloride (119 g, 1.0 mol) was added dropwise, and the temperature was raised to 70°C for 2 hours of reaction. Cooling, it is slowly transferred to the mixed ice water of 1000 grams of crushed ice and 500 grams of water, filtered, washed with water, and dried to obtain 178 grams of light yellow 3-methylquinoline-8-sulfonyl chloride crude product, the yield is 74 %. Toluene was recrystallized to obtain 162 g of off-white pure product with a yield of 91%. Melting point: 16...
Embodiment 2
[0040] Add chlorosulfonic acid (233 grams, 2.0 moles) in the 500 milliliters four-neck reaction flasks with mechanical stirrer, thermometer, reflux condenser and feeding port, at 25 ℃, drop into 3-methylquinoline (143 g, 1.0 mol), followed by the addition of ammonium chloride (5 g, 0.1 mol). After the addition, the reaction was carried out at a constant temperature of 25° C. for 1 hour, then the temperature was raised to 120° C., and the reaction was carried out for 4 hours. The temperature was lowered to 50°C, thionyl chloride (119 g, 1.0 mol) was added dropwise, and the temperature was raised to 70°C for 2 hours of reaction. The post-treatment process of the reaction was the same as in Example 1 to obtain 169 g of light yellow 3-methylquinoline-8-sulfonyl chloride crude product with a yield of 70%. Toluene was recrystallized to obtain 152 g of off-white pure product with a yield of 90%. Melting point: 161-162°C.
[0041] The content of 3-methylquinoline-8-sulfonyl chlorid...
Embodiment 3
[0043] Add chlorosulfonic acid (233 grams, 2.0 moles) in the 500 milliliters four-neck reaction flasks with mechanical stirrer, thermometer, reflux condenser and feeding port, at 25 ℃, drop into 3-methylquinoline (143 g, 1.0 mol), and then sodium sulfate (14 g, 0.1 mol) was added. After the addition, the reaction was carried out at a constant temperature of 25° C. for 1 hour, then the temperature was raised to 120° C., and the reaction was carried out for 4 hours. The temperature was lowered to 50° C., phosphorus pentachloride (177 g, 1.0 mol) was added dropwise, and the temperature was raised to 80° C. to react for 3 hours. The post-treatment process of the reaction was the same as in Example 1 to obtain 193 g of light yellow 3-methylquinoline-8-sulfonyl chloride crude product with a yield of 80%. Recrystallization from toluene gave 181 g of off-white pure product with a yield of 94%. Melting point: 161-162°C.
[0044] The content of 3-methylquinoline-8-sulfonyl chloride w...
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