反应详情

To a solution of 5-amino-3-methylisoxazole (0.165 g, 1.67 mmol) in anhydrous toluene (6.5 ml) and anhydrous pyridine (0.18 ml, 2.0 mmol) cooled in an ice/water bath (T=˜10° C.) was slowly added bromoacetyl bromide (0.402 g, 2.0 mmol). The reaction mixture was stirred for 1.5 h under argon, then poured into water (20 ml), and extracted with ethyl acetate (2×40 ml). The combined organics were washed with water (30 ml), brine (30 ml), dried (Na2SO4), and concentrated in vacuo. The residue was triturated with diethyl ether, the precipitate was removed by filtration, and the filtrate was concentrated in vacuo to afford the title compound as a white solid (0.200 g, 55%); 1H-NMR (500 MHz, DMSO-d6) 2.18 (s, 3H, CH3), 4.08 (s, 2H, CH2Br), 6.15 (s, 1H, isoxazole C—H), 11.94 (s, 1H, CONH);

1. extractionextracted with ethyl acetate (2×40 ml)
2. washThe combined organics were washed with water (30 ml), brine (30 ml)
3. dry with materialdried (Na2SO4)
4. concentrationconcentrated in vacuo
5. customThe residue was triturated with diethyl ether
6. customthe precipitate was removed by filtration
7. concentrationthe filtrate was concentrated in vacuo