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

Reaction equation

[S:1]1[C:5]2[C:6]3[C:11]([CH:12]=[CH:13][C:4]=2[NH:3][C:2]1=[O:14])=[CH:10][CH:9]=[CH:8][CH:7]=3.[CH3:15][O:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][O:22][CH:23](I)[CH3:24].[OH-].[K+]>C(O)C>[CH3:15][O:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][O:22][CH2:23][CH2:24][N:3]1[C:4]2[CH:13]=[CH:12][C:11]3[C:6]([C:5]=2[S:1][C:2]1=[O:14])=[CH:7][CH:8]=[CH:9][CH:10]=3

Participants

Procedure

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.