Dimethylamine → 1H-benzoimidazole-4-carboxylic acid dimethylamide

Participants

Reaction Steps

To a stirred solution of 1H-benzoimidazole-4-carboxylic acid hydrochloride (1 g, 5.04 mmol), dimethylamine (2M in THF; 3.78 mL, 7.55 mmol) and ethyldiisopropylamine (3.51 mL, 20.1 mmol) in DMF (5.0 mL) at room temperature was added O-benzotriazole-N,N,N′,N′-tetramethyl-uronium-hexafluoro-phosphate (1.95 g, 5.14 mmol) in a single portion. The mixture was stirred at room temperature overnight then concentrated in vacuo. The product was purified by SiO2 chromatography followed by trituration with Et2O providing 1H-benzoimidazole-4-carboxylic acid dimethylamide (730 mg).

Provenance & Evidence