Sodium Hydroxide → HCID 11350681, compound

Participants

Reaction Conditions

Reaction Steps

N-(4-chloro-3-methylisothiazol-5-yl)-[2-(2-methylpropyl)indazol-5-yl]acetamide (0.50 g, 0.0014 mol) was dissolved in dichloromethane (15 ml) and the solution was cooled to 5° C. Chloromethyl ethyl ether (0.32 ml, 0.0035 mol), 50% aqueous sodium hydroxide solution (0.56 ml) and benzyltriethylammonium chloride (0.018 g) were added sequentially and then the mixture was stirred for 2 hours. The mixture was diluted with dichloromethane, washed with water, dried over anhydrous magnesium sulfate, filtered and the filtrate was evaporated in vacuo. The residue was purified by flash column chromatography on silica gel, initially eluting with 3:1 diethyl ether:hexane, then with diethyl ether and finally with ethyl acetate to give N-(4-chloro-3-methylisothiazol-5-yl)-N-(ethoxymethyl)-[2-(2-methylpropyl)indazol-5-yl]acetamide (0.16 g) as a yellow oil and N-[2-ethoxymethyl-4-chloro-3-methylisothiazolin-5-ylidene]-[2-(2-methylpropyl)indazol-5-yl) acetamide (0.20 g) as a cream-coloured solid (m.p. 105–106° C.).

Provenance & Evidence