4-Methylmorpholine → HCID 44132729, compound

Participants

Reaction Steps

100 mg (0.874 mmol) of 1,3-cyclohexanedione, 150 mg (0.874 mmol) of 4-(hydroxyethoxy)benzaldehyde and 92 mg (0.874 mmol) of 2-cyanoethanethioamide were initially charged in 2.9 ml of ethanol and stirred with 179 mg (1.748 mmol) of N-methylmorpholine at RT overnight. 213 mg (0.874 mmol) of 4-(chloromethyl)-2-(4-chlorophenyl)-1,3-thiazole were then added, and the mixture was stirred at RT for a further 2.5 hours. The reaction mixture was diluted with water and dichloromethane, the two phase were separated and the aqueous phase was extracted four times with dichloromethane. The combined organic phases were washed in each case once with 0.5 N hydrochloric acid and saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered and concentrated. The crude product was purified by preparative HPLC [Chromasil, water/acetonitrile+0.15% hydrochloric acid].

Provenance & Evidence