Benzothiazole → HCID 44239811, compound

Temperature

60 °C

H2O2 (30% in H2O; 0.31 mL, 3.0 mmol) was added dropwise over 1-2 min to a stirred solution of benzothiazole 1f (108 μL, 1.0 mmol), concentrated H2SO4 (107 μL, 2.0 mmol), 3-iodooxetane (368 mg, 2.0 mmol) and iron(II) sulfate heptahydrate (80 mg, 0.3 mmol) in DMSO (10 mL) at 60 °C. After 1-2 min a further portion of iron(II) sulfate heptahydrate (80 mg, 0.3 mmol) was added and the mixture was stirred at 60 °C for 30 min. Further H2O2 (0.31 mL, 3.0 mmol) and iron(II) sulfate heptahydrate (80 mg, 0.3 mmol) was added, and the mixture was stirred at 60 °C for 60 min. After allowing to cool, the mixture was poured into a 0.2 M solution of NaOH (30 mL) and Et2O (50 mL). The aqueous and organic layers were partitioned and the aqueous layer was extracted - 7 -with Et2O (2 x 25 mL). The combined organic extracts were washed with brine (1 x 30 mL), dried (MgSO4), filtered and the solvent removed under vacuum to leave a crude oil. The oil was purified by preparative thin-layer chromatography using EtOAc / hexanes (3:7) as eluent to give recovered benzothiazole 1f (60 mg, 44%), and the desired product 2f (58 mg, 30%).

ORD record

ord-065a25a8e27e42e0a91bfb691ac92afa

Source dataset

Minisci dataset from Roche

DOI

10.1021/jo9010624