Methyl iodide → 2-(Methylthio)-5-nitrobenzo[d]oxazole

Participants

Reaction Conditions

Reaction Steps

Suspend 5-nitro-3H-benzooxazole-2-thione (5.15 g, 26.3 mmol) in THF (150 mL). Cool in an ice bath to 5° C. and add sodium hydride (60% dispersion in mineral oil) (1.7 g, 42.5 mmol). Stir for 15 min at 5° C. Add dropwise iodomethane (5.0 mL, 80.1 mmol) dissolved in THF (30 mL) over 1 h. Continue to stir at room temperature for 4 h. Absorb the reaction mixture onto silica gel, and purify using silica gel chromatography, eluting with a gradient of EtOAc in hexane (0-60%) to afford the title compound (4.75 g, 86%). 1H NMR (400 MHz, DMSOd6): δ 8.47 (d, 1H, J=3.1 Hz), 8.24 (dd, 1H, J=9.0, 2.4 Hz), 7.89 (d, 1H, J=8.8 Hz), 2.81 (s, 3H).

Provenance & Evidence