Hydrochloric Acid → HCID 57709598, compound

1-Phenyl-2-(2H-tetrazol-5-yl)-ethanone (3.3 g, 17.5 mmol), ethyl iodide (1.4 g, 17.5 mmol) and potassium carbonate (2.4 g, 17.5 mmol) was heated at reflux in acetone (50 mL) for 5 h under argon. The reaction mixture was then poured into water, made acidic with 6M HCl and extracted with diethyl ether. The organic extract was dried and evaporated to a red/orange oil. The oil was dissolved in diethyl ether (100 mL) and bromine (17.5 mmol) was added. The mixture was stirred over night at ambient temperature, then the solvent was removed in vacuo and the residue was redissolved in ethanol (100 mL). Thiourea (35 mmol) was added, and the resulting mixture was heated at reflux for 10 min., after which a solid precipitated. The reaction mixture was poured into water containing NaOH (17.5 mmol), and the orange crude product was recovered by filtration. The crude product was recrystallized from acetonitrile to give pale yellow solid. Yield: 0.6 g, 17%.

1. extractionextracted with diethyl ether
2. extractionThe organic extract
3. customwas dried
4. customevaporated to a red/orange oil
5. dissolutionThe oil was dissolved in diethyl ether (100 mL)
6. customthe solvent was removed in vacuo
7. dissolutionthe residue was redissolved in ethanol (100 mL)
8. temperaturethe resulting mixture was heated
9. temperatureat reflux for 10 min.
10. customafter which a solid precipitated
11. additionThe reaction mixture was poured into water
12. filtrationthe orange crude product was recovered by filtration
13. customThe crude product was recrystallized from acetonitrile
14. customto give pale yellow solid

ORD record

ord-3cc470bf08de49578e814dc0c3afa2c6

Source dataset

uspto-grants-2011_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07910613B2