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0 °C

2-{{1-(1-Naphthalenyl)-1H-tetrazol-5-yl}thio}acetic acid (500 mg, 1.75 mmol) and 2-chloroaniline (202 μL, 1.92 mmol) were dissolved in dry pyridine (8 mL). This solution was cooled to 0° C. and POCl3 (0.179 mL) was added dropwise. The mixture was stirred at 0° C. for 1 h, quenched with a few drops of water, and concentrated under reduced pressure. The crude product was dissolved in CH2Cl2 (100 mL) and the resulting solution was successively washed with water (2×30 ml) and brine (30 ml), dried (MgSO4), filtered and concentrated under reduced pressure. The crude product was purified by flash column chromatography (CH2Cl2:(CH3)2CO, 95:5) to afford the title compound (643 mg, 85% yield) as a solid.

1. customquenched with a few drops of water
2. concentrationconcentrated under reduced pressure
3. dissolutionThe crude product was dissolved in CH2Cl2 (100 mL)
4. washthe resulting solution was successively washed with water (2×30 ml) and brine (30 ml)
5. dry with materialdried (MgSO4)
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure
8. customThe crude product was purified by flash column chromatography (CH2Cl2:(CH3)2CO, 95:5)