Potassium Carbonate → HCID 71620987, compound

Participants

Reaction Conditions

Reaction Steps

A 50 mL flask fitted with a stir-bar and a septum with an Ar inlet was charged with 2-(phenoxymethyl)-1 H-benzimidazole (61) (1.00 g, 4.46 mmol), K2CO3 (1.23 g, 8.92 mmol), and DMF (12 mL). 3-Methoxybenzyl chloride (769 mg, 4.91 mmol) was added, and the suspension was heated in a 100° C. bath for 2 hr. The mixture was cooled, and the solids were filtered off and rinsed with EtOAc (50 mL). The filtrate was then washed with sat'd NH4Cl (2×30 mL), H2O (2×30 mL), and brine (20 mL), filtered through phase separation paper, and concentrated in vacuo to a yellow oil. Upon standing the oil crystallized, and was subsequently collected with hexanes:EtOAc 30:1 (15 mL). Upon drying, 1.41 g of Compound #11 were obtained as an off-white crystalline solid (92%). 1H NMR (300 MHz, CDCl3): δ 7.84 (m, 1H), 7.36-7.25 (m, 5H), 7.21 (t, 1H), 6.82 (dd, 1H), 6.68 (d, 1H), 6.62 (m, 1H), 5.52 (s, 2H), 5.36 (s, 2H), 3.64 (s, 3H) ppm. HPLC analysis (5:10:85 H2O:A1:MeOH) showed a purity of greater than 99% with a retention time of 4.8 min.

Provenance & Evidence