Potassium Hydroxide → 3-Methoxyethoxyethoxyethylnaphtho[2,1-d]thiazolin-2-on

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Reaction Steps

2.0 g of naphtho[2,1-d]thiazoline-2-on, 3.0 g of 2-methoxyethoxyethoxy-1-iodoethane (synthesized from methoxyethoxyethoxyethyl p-toluenesulfonate and sodium iodide), 0.6 g of potassium hydroxide and 20 ml of ethanol were fed into a 50 ml short-neck flask provided with a reflux condenser, and heated under reflux and under stirring for 4 hours. After cooling to room temperature followed by extraction with 300 ml of ethyl acetate and 150 ml of water, the thus-obtained ethyl acetate layer was dried over sodium sulfate, and ethyl acetate was distilled off under reduced pressure. The obtained compound was purified by column chromatography (hexane:ethyl acetate=1:1) to obtain the intended compound.

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