Sodium Bicarbonate → HCID 178495897, 화합물

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N-Hydroxy-4-[(2-methoxyethyl)amino]-1,2,5-oxadiazole-3-carboximidoyl chloride (46.0 g, 0.208 mol) was mixed with water (300 mL). The mixture was heated to 60° C. 3-Bromo-4-fluoroaniline [Oakwood products, product #013091] (43.6 g, 0.229 mol) was added and stirred for 10 min. A warm sodium bicarbonate (26.3 g, 0.313 mol) solution (300 mL water) was added over 15 min. The reaction was stirred at 60° C. for 20 min. LCMS indicated reaction completion. The reaction solution was cooled to room temperature and extracted with ethyl acetate (2×300 mL). The combined ethyl acetate solution was dried over sodium sulfate and concentrated to give the desired product (76.7 g, 98%) as a crude brown solid. LCMS for C12H14BrFN5O3 (M+H)+: m/z=374.0, 376.0. 1H NMR (400 MHz, DMSO-d6): δ 11.55 (s, 1 H), 8.85 (s, 1 H), 7.16 (t, J=8.8 Hz, 1 H), 7.08 (dd, J=6.1, 2.7 Hz, 1 H), 6.75 (m, 1 H), 6.14 (t, J=5.8 Hz, 1 H), 3.48 (t, J=5.2 Hz, 2 H), 3.35 (dd, J=10.8, 5.6 Hz, 2 H), 3.22 (s, 3 H).

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