Acetonitrile, 2,2-diethoxy- → Methyl 2,2-diethoxyethanecarboximidate

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Reaction Steps

To a stirred solution of diethoxyacetonitrile (5 g, 38.75 mmol) in dry methanol (80 mL) was added 1 mL of a 20% solution of sodium methoxide. After the addition, the reaction mixture was stirred at RT for 24 h, quenched with solid CO2, and then concentrated. The resulting residue was diluted with water and extracted with chloroform. The organic layer was washed with brine and dried over Na2SO4 to yield methyl 2,2-diethoxyacetimidate (6 g, 96%). 1H NMR (400 MHz, DMSO-d6) δ (ppm): 7.95 (s, 1H),), 4.82 (s, 1H), 3.66 (s, 3H), 3.49 (q, 4H, J=7.2 Hz); 1.16-1.13 (t, 3H, J=7.2 Hz).

Provenance & Evidence