Methanol → HCID 19802731, compound

Participants

Reaction Steps

A solution of 200 mg (0.52 mmol) of 3-butyl-5-(4-chlorobenzylthio)-4-(4-hydroxybenzyl) -4H-1,2,4-triazole (from Step A) in 2 ml of dry DMF was treated with 21 mg (0.52 mmol) of sodium hydride (60% in oil), and the mixture was stirred under N2 at room temperature for a few minutes until H2 evolution had ceased and a clear solution had resulted. To this was added 119 mg (0.52 mmol) of methyl α-bromophenylacetate, and stirring was continued under N2 at room temperature for 10 minutes and then at 65° C. for 6 hours. The cooled mixture was treated with 1 ml of MeOH and then concentrated in vacuo. The residue was partitioned between 25 ml of EtOAC and 30 ml of H2O. The EtOAc phase was washed with 2×25 ml of H2O and then with 25 ml of saturated NaCl. The organic solution was dried over MgSO4, filtered, and concentrated. Column chromatography of the residue on silica gel (gradient elution with 0.75-1.2% MeOH in CH2Cl2) yielded 191 mg (69%) of the title compound as a glass; homogeneous by TLC in 97:3 CH2Cl2 -MeOH.

Provenance & Evidence