1,1'-Carbonyldiimidazole → HCID 66813314, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-(4-bromobenzylamino)-N-cyclopropylacetamide (7H4) (28.3 mmol, 8.0 g) in acetonitrile (200 ml) was added carbonyldiimidazole (56.5 mmol, 9.16 g) and 4-dimethylaminopyridine (56.5 mmol, 6.90 g). The reaction mixture was heated to 60° C. and stirred overnight before cooling to room temperature. Saturated sodium bicarbonate solution was added and the mixture extracted with EtOAc (×3). The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated and the residue purified on silica eluting with heptane/acetone 9:1 to 7:3 to give 1-(4-bromobenzyl)-3-cyclopropylimidazolidine-2,4-dione (7H5) 8.3 g (98%); 1H NMR (400 MHz, CDCl3) δ 7.50 (d, 2H) 7.13 (d, 2H) 4.50 (s, 2H) 3.66 (s, 2H) 2.62 (m, 1H) 0.97 (d, 4H).

Provenance & Evidence