Dimethylformamide dimethyl acetal → HCID 67519860, compound

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Reaction Steps

A 50 ml round bottom flask is charged with the 1-[6-(2-chlorophenyl)imidazo[2,1-b][1,3]oxazol-5-yl]ethanone (952 mg, 3.65 mmol) and dimethylformamide dimethylacetal (22 ml). The mixture is refluxed for 5 hours and then cooled to room temperature. The mixture is diluted with ethyl acetate (150 ml) and washed three times with 100 ml each of a saturated sodium chloride solution. The organic phase is dried with magnesium sulfate, filtered and concentrated in vacuo, to give a brown oil. The product is purified by flash chromatography on silica gel (ethyl acetate), yielding 604 mg of a pale brown solid (52%). M.p.=187-189° C.; 300 MHz 1H NMR (CDCl3) δ: 8.07 (d, J=1.6 Hz, 1H), 7.62-7.35 (m, 6H), 4.78 (d, J=12.5 Hz), 1H), 3.04-3.01 (m, 3H), 2.4-2.32 (m, 3H). LCMS: 316[M+H]; calc. for C16H14ClN3O2: C, 60.76; H, 4.49; N, 13.28; found. C, 60.81; H, 4.39; N, 13.35.

Provenance & Evidence