Water → 2-Chloro-4-[[1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethoxy]methyl]quinoline

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Reaction Conditions

Reaction Steps

In a three necked flask, fitted with stirrer, reflux condenser and gas inlet tube are introduced 30 g of sodium hydroxide (0.75 mol) and 30 ml of water. While passing nitrogen through the flask, the solution is cooled to 45° C. and then are added 7.7 g of 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethanol (0.03 mol), 0.5 g of benzyltrimethylammonium chloride, 100 ml of tetrahydrofuran and 6.4 g of 2-chloro-4-chloromethylquinoline (0.03 mol). Then the mixture is stirred vigorously for 1.5 hours at 60°-65° C. After cooling the mixture is separated, and the lower aqueous sodium hydroxide is extracted with 20 ml of tetrahydrofuran. The combined tetrahydrofuran layers are dried with sodium sulfate, charcoaled, filtered and after the solvent has been removed, the residual oil is extracted with 175 ml of ether, and the etheral solution is allowed to stand overnight in a refrigerator. The crystallized 2-chloro-4-[[1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethoxy]methyl]quinoline is recrystallized from ethyl acetate (refrigerator). Yield 5.5 g (42.3%); m.p. 180°-181° C.

Provenance & Evidence