Bromoacetyl chloride → Acetanilide

Participants

Reaction Conditions

Reaction Steps

To a 100 mL flask was added 4-ethylamino-3-nitroaniline (1.1 g, 6.3 mmol) and anhydrous CHCl3 (45 mL). The solution was cooled to 0° C. prior to the addition of bromoacetyl chloride (0.62 mL, 7.5 mmol) and TEA (1.7 mL, 13 mmol) under a nitrogen atmosphere. The reaction mixture was allowed to warm to ambient temperature over 1 h before the solvent was removed under reduced pressure. The crude material was chromatographed (SiO2, 0–40% EtOAc/Hex) to provide the intermediate acetanilide (540 mg, 1.8 mmol) as a red solid. To a solution of the intermediate in anhydrous DMF (25 mL) was added sodium acetate (1.41 g, 17.2 mmol). The suspension was heated at 100° C. for 4 h. After cooling, the reaction mixture was diluted with EtOAc (25 mL), and the excess sodium acetate was removed by filtration under reduced pressure. The filtrate was concentrated under reduced pressure to provide the title compound (420 mg). 1H-NMR (CDCl3): δ 8.13 (1H, br s), 8.11 (1H, d), 7.90 (1H, br s), 7.79 (1H, dd), 6.80 (1H, d), 4.68 (2H, s), 3.33 (2H, m), 2.21 (3H, s), 1.35 (3H, t); MS(ESI): 282 (MH+).

Provenance & Evidence