Sulfuric Acid → HCID 86730870, compound

Participants

Reaction Steps

1-methyl-3-(1-methylpropyl)tetrazolium-5-thiolate (173.7 mg, 1.0 mmol) was introduced into a recovery flask; concentrated sulfuric acid (1.7 mL) and C2H5(CH3)CHOH (s-BuOH, 92.0 μL, 1.0 mmol) were added to this; and stirring was performed for 13 hours. Then, while on an ice bath, an aqueous sodium hydroxide solution (30.0 mmol, 10 mL) and aqueous sodium bicarbonate (30.0 mmol, 10.0 mL) were added dropwise using a dropping funnel. More aqueous sodium bicarbonate was added to bring to neutrality (pH=6-7). Extraction with methylene chloride, washing with an aqueous sodium carbonate solution, drying over anhydrous sodium sulfate, and distillation of the solvent yielded a yellow liquid. On the other hand, sodium fluoroborate (165.0 mg, 1.5 mmol) was added to the water layer followed by extraction with methylene chloride, drying over anhydrous sodium sulfate, and removal of the solvent by distillation to obtain 1-methyl-3-(1-methylpropyl)-5-(1-methylpropylthio)tetrazolium tetrafluoroborate (yield=237.1 mg, 75%).

Provenance & Evidence