N-bromobutanimide → HCID 57550202, compound

Participants

Reaction Steps

A solution of 1-{4-[4-(chloromethyl)-1,3-oxazol-2-yl]benzyl}-1H-benzimidazole (0.40 g, 1.24 mmol) in dry chloroform was treated with N-bromosuccinimide (NBS) (0.24 g, 1.36 mmol), stirred at room temperature for 1 h and concentrated in vacuo. The resultant residue was partitioned between CH2Cl2 and water. The organic phase was separated, washed with brine, dried over Na2SO4 and concentrated under reduced pressure. This residue was purified by column chromatography (silica, CH2Cl2:MeOH 98:2) to afford the title compound in 56% yield, identified by NMR and mass spectral analyses. 1H NMR (300 MHz, DMSO-d6): 8.43 (s, 1H), 7.93 (m, 2H), 7.59-7.76 (m, 1H), 7.47-7.53 (m, 1H), 7.45 (m, 2H), 7.10-7.31 (m, 2H), 5.60 (s, 2H), 4.65 (s, 2H). LCMS (ESI+) 402, 404 (MH+).

Provenance & Evidence