Ethanol → 5-Ethylsulfonyl-1-phenyl-1H-tetrazole

Participants

Reaction Steps

To a solution of 1-Phenyl-5-mercaptotetrazole (25 g, 140 mmol) in ethanol (250 mL) was added powdered potassium hydroxide (9.5 g). The resulting mixture was refluxed for 1 h, and ethyl iodide (12 mL, 150 mmol) was added drop wise. The reaction proceeded under reflux for 18 h. After cooling, the volatiles were removed under reduced, pressure and the residue was partitioned between water (300 mL) and ether (300 mL). The organic layer was washed with sat. NaHCO3 (2×120 mL) and brine (100 mL). After concentration in vacuo, the residue (28.71 g) was taken up in methanol (250 mL) and water (250 mL). After cooling to 0 C, Oxone (400 g) was added portion wise. The mixture was then stirred for 1 h at room temperature before refluxing for 18 h. After cooling, ether (300 mL) was added and the solids were removed by filtration. The filtrate was then concentrated in vacuo, and the white solid was filtered. The latter was thoroughly washed with water and dried under reduced pressure over night to yield 5-Ethylsulfonyl-1-phenyl-1H-tetrazole (27.7 g, 116 mmol) as a white solid.

Provenance & Evidence