Hydrochloric Acid → 3-[5-(4-Cyano-phenyl)-[1,3,4]thiadiazol-2-ylmethyl]-benzoic acid

Participants

Reaction Conditions

Reaction Steps

Suspend 3-[5-(4-cyano-phenyl)-[1,3,4]thiadiazol-2-ylmethyl]-benzoic acid methyl ester (0.15 g, 0.45 mmol) in 10 mL of a 1:1 mixture of H2O:MeOH, add 10% aqueous solution of NaOH (0.48 mL, 1.20 mmol) and heat to 60° C. After stifling for 3 h add 5 mL of THF to the reaction mixture causing all of the solids to go into solution. Heat the mixture at 60° C. for an additional 2 h then cool to room temperature. Adjust the pH to slightly acidic by the addition of a 2N solution of HCl. Dilute the mixture with H2O and wash with CH2Cl2. Wash the combined organics with brine, dry over anhydrous sodium sulfate and concentrate to provide 0.13 g, 57% yield of 3-[5-(4-cyano-phenyl)-[1,3,4]thiadiazol-2-ylmethyl]-benzoic acid as a solid.

Provenance & Evidence