Triethylamine → HCID 19802761, compound

Participants

Reaction Steps

A suspension of 3-butyl-4-[[4-[1-carbamoyl-1-phenylmethoxy]phenyl]methyl]-5-(4-nitrobenzylthio)-4H-1,2,4-triazole (from Example 3, Step A) in phosphorus oxychloride (25-30 equivalents) is stirred at 0° C. under N2 as triethylamine (2.2 equivalents) is added dropwise over about 1 hours. After the addition is complete, the mixture is gradually warmed to room temperature and then heated to reflux for about 45 minutes or until TLC indicates complete reaction. The cooled mixture is concentrated in vacuo, and the residue is partitioned between ice-water and an organic solvent, such as ether, ethyl acetate, or toluene. The organic phase is washed with dilute NaOH and then with H2O. The organic solution is dried over MgSO4, filtered, and concentrated to give the title compound, which is used directly or may be purified by chromatography on silica gel.

Provenance & Evidence