反应详情

To a solution of 2-Benzoylsulfanyl-benzoic acid (as prepared in step 1 above; 1 g, 3.88 mmol) in anhydrous CH2Cl2 (40 mL), was added oxalyl chloride (2 mL, 22.5 mmol) followed by 2 drops of DMF. The suspension was stirred at room temperature until a clear solution was obtained. The solvent was evaporated under reduced pressure and the remaining crude solid was dissolved in anhydrous THF (40 mL). NEt3 (0.29 g, 2.5 mmol) and 2,5-Dimethyl-2H-pyrazol-3-ylamine (0.432 g, 3.88 mmol) were then added and the solution was allowed to stir at 50° C. overnight. The reaction mixture was diluted with EtOAc (60 mL) and extracted with H2O (3×50 mL) and saturated NaHCO3(aq). The organics were then dried over Na2SO4, filtered, concentrated in vacuo. The crude residue was purified via column chromatography (30% EtOAc/Hexanes) to give pure thiobenzoic acid S-[2-(2,5-dimethyl-2H-pyrazol-3-ylcarbamoyl)-phenyl]ester in 71% yield (0.966 g, 2.75 mmol).

1. customwas obtained
2. customThe solvent was evaporated under reduced pressure
3. dissolutionthe remaining crude solid was dissolved in anhydrous THF (40 mL)
4. stirringto stir at 50° C. overnight
5. extractionextracted with H2O (3×50 mL) and saturated NaHCO3(aq)
6. dry with materialThe organics were then dried over Na2SO4
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. customThe crude residue was purified via column chromatography (30% EtOAc/Hexanes)