Nitrogen → 475648-88-5

Participants

Reaction Steps

To a three-necked, 12 L flask, flushed with N2, 2-(chloromethyl)benzimidazole (75 g, 0.45 mmol) and THF (10 L) were added, and the slurry was stirred for one hour at room temperature. Using an ice bath, the slurry was cooled to 0° C. and NaH (5.7 g, 95%, 0.23 mmol) was added. The slurry temperature increased to 4.5° C. The reaction mixture was stirred for 3 h and quenched with 150 g of silica gel. The slurry was concentrated to dryness under reduced pressure and purified using column chromatography (loaded with 40% EtOAc/hexanes, the eluting solvent started with 40% EtOAc/hexanes to end with 75% EtOAc/hexanes). 14.8 g of 1-benzimidazolylmethyl-2-(chloromethyl)benzimidazole 1 was obtained.

Provenance & Evidence