Imidazole → HCID 18930613, compound

Participants

Reaction Steps

Phosphorus oxychloride (2.2 ml, 24 mmol), imidazole (2.7 g, 40 mmol), and N-benzyloxycarbonylglycine (5.0 g, 24 mmol) are added to dimethylacetamide (32 ml) under ice cooling and stirring. After stirring for 5 minutes, a solution of 2-iodoaniline (4.4 g, 20 mmol) in DMA (10 ml) is added dropwise. The reaction mixture is stirred at 50° C. for 3 hours. After allowing to cool, water and ethyl acetate are added to the reaction mixture, and a saturated aqueous solution of sodium hydrogencarbonate is added to make pH 9, and the aqueous phase is extracted twice with ethyl acetate. The organic layer is washed with a saturated saline, dried over anhydrous magnesium sulfate, and then concentrated. To the residue is added isopropylether (40 ml), and the precipitated solid is filtered off to obtain the objective compound (7.10 g). Yield 86%.

Provenance & Evidence