Dimethylamine → 2-amino-3-fluoro-5-iodo-N,N-dimethyl-benzamide

Participants

Reaction Conditions

Reaction Steps

550 mg (1.79 mmol) of 8-fluoro-6-iodo-1H-benzo[d][1,3]oxazine-2,4-dione was combined with 4 mL tetrahydrofuran in a 15 mL-sized sealed tube. To the solution was added 1.79 mL (3.58 mmol) of a 2.0 M dimethylamine solution in tetrahydrofuran. The sealed tube was capped and heated in an oil bath at 60° C. for 48 hours. The solution was concentrated down and then purified by flash chromatography on silica gel. A gradient of ethyl acetate and hexanes was used to afford 368 mg (1.19 mmol, 67% yield) of 2-amino-3-fluoro-5-iodo-N,N-dimethyl-benzamide as a golden oil. 1H NMR (500 MHz, CDCl3) δ 7.29 (dd, 1H), 7.19 (s, 1H), 4.50 (s, br., 2H), 3.03 (s, br., 6H).

Provenance & Evidence