Benzyl Bromide → 2-(Benzylthio)-5-phenyl-1,3,4-oxadiazole

Temperature

0 °C

5-Phenyl-[1,3,4]oxadiazole-2-thiol (Aldrich, 3.1 g, 17.4 mmol) was added to EtOH (30 mL) and cooled to 0° C. while stirring. Diisopropylethylamine (3.1 mL, 17.4 mmol) was then added and the mixture became a clear solution. Benzyl bromide (2.08 mL, 17.4 mmol) was added and the resulting mixture was allowed to warm to room temperature while stirring. After 45 min, a thick white precipitate formed. The mixture was stirred an additional 1 hr followed by the addition of 1M NaOH (3 mL). The mixture was filtered, washed with 1M NaOH (2×20 mL), 3% citric acid (2×20 mL), H2O (2×20 mL) and the precipitate was dried under vacuum to afford 4.31 g (92%) 2-benzylsulfanyl-5-phenyl-[1,3,4]oxadiazole as a white solid. 1H NMR (CDCl3, 300 MHz) δ 4.57 (s, 2H), 7.37 (m, 3H), 7.48 (m, 5H), 7.99 (m, 2H); MS (DCl/NH3) m/z 269 (M+H)+.

1. temperatureto warm to room temperature
2. stirringwhile stirring
3. customa thick white precipitate formed
4. stirringThe mixture was stirred an additional 1 hr
5. filtrationThe mixture was filtered
6. washwashed with 1M NaOH (2×20 mL), 3% citric acid (2×20 mL), H2O (2×20 mL)
7. customthe precipitate was dried under vacuum

ORD record

ord-6eaad836a3b5496698812e6d8455ff1a

Source dataset

uspto-grants-2011_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07872010B2