Water → HCID 11771561, compound

Participants

Reaction Steps

To a solution of 5-amino-2-bromo-N, 4-dimethylbenzamide (3A) (94 mg, 0.38 mmol) in acetone (4 mL) at 0° C. was added DIPEA (68 μL, 0.39 mmol) followed by 2-chloroacetylchloride (31 μL, 0.39 mmol). The solution was stirred for 60 minutes and another aliquot of 2-chloroacetylchloride (4 μL) was added. Water was added (94 mL) and the acetone removed in vacuo. The solids were stirred rapidly for 1 h, filtered and washed with water to give 104 mg (84% yield) of 2-bromo-5-(2-chloroacetamido)-N-methyl-4-methylbenzamide, 1H NMR: (CDCl3, 400 MHz) δ 8.28 (s, 1H), 8.03 (s, 1H), 7.44 (s, 1H), 6.01 (br s, 1H), 4.23 (s, 2H), 3.01 (d, J=5.0 Hz, 3H), 2.17 (s, 3H); LCMS 320.99 (M+H).

Provenance & Evidence