Hydrochloric Acid → HCID 11695088, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-ethoxy-7-methoxy-3-(4-methoxyphenyl)-4(3H)-quinazolinone (0.0080 g, 0.0245 mmol), as prepared in Example 41, in dimethylformamide (0.25 mL), was added sodium ethanethiolate (0.0047 g, 0.0563 mmol). The resulting suspension was warmed to 120° C. to form a solution. After each hour (for 7 hours) additional sodium ethanethiolate (0.0047, 0.0563 mmol) was added. After 7 hrs, the cloudy orange reaction solution was cooled to room temperature and diluted with water (0.75 mL). The resulting yellow solution was acidified with 1.0N HCl to pH 3 wherein the reaction solution became cloudy. Extraction was performed with EtOAc (3×) and dichloromethane (3×). The combined organic layers were washed with brine (1×), dried over MgSO4, filtered, and concentrated. Column chromatography (5% MeOH in CH2Cl2) gave 0.0017 g (23%) of 5-ethoxy-7-hydroxy-3-(4-hydroxyphenyl) quinazoline-4-one, as a white solid.

Provenance & Evidence