Hydrochloric Acid → HCID 21997539, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of a mixture of methyl 4-[5-(4-hydroxyphenyl)-1,3,4-thiadiazol-2-yl]benzoate and 4-[5-(4-hydroxyphenyl)-1,3,4-thiadiazol-2-yl]benzoic acid (3.12 g), potassium carbonate (22.07 g) and N,N-dimethylformamide (15 ml) was added 1,5-dibromopentane (15 ml) and the mixture was stirred at 100° C. (bath temperature) for 5 hours. The resulting mixture was neutralized by 0.1N hydrochloric acid and extracted with dichloromethane. The organic layer was washed with brine and dried over magnesium sulfate. The solvents were removed under reduced pressure and the residue was triturated with n-hexane. The solid was collected by filtration and dried to give a crude powder (3.71 g). To the crude powder (2.11 g) was added methanol (100 ml) and sodium methoxide (28% in methanol) (10 ml), and refluxed for 2 hours. Then to the reaction mixture was added sodium methoxide (28% in methanol) (5 ml) and refluxed for 1.5 hours. After cooling, the reaction mixture was added to water and tetrahydrofuran, stirred overnight and adjusted to pH 2 with 4N hydrochloric acid. The resulting precipitate was collected by filtration, washed with acetonitrile and dried under reduced pressure to give 4-[5-[4-(5-methoxy-n-pentyloxy) phenyl]-1,3,4-thiadiazol-2-yl]benzoic acid (1.34 g).

Provenance & Evidence