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

In a 2 L three-neck flask, a solution of diethoxyacetonitrile (125 g, 968 mmol) in methanol (300 mL, anhydrous) was treated with a 25 wt % solution of sodium methoxide (21.0 g, 389 mmol) in methanol, producing a slightly exothermic reaction. After cooling, the mixture was stirred at room temperature for 15 h. Upon completion of the reaction, the solvent was slowly evaporated under vacuum. The remaining brown-colored residue was solvated with diethyl ether (1 L), then washed with water (3×500 mL), followed by brine (1×200 mL). The organic layer was dried using magnesium sulfate, the salts filtered, and the solvent evaporated carefully under vacuum to afford 132 g (85% yield) of methyl 2,2-diethoxyethanimidoate as a colorless liquid.

1. customproducing
2. customa slightly exothermic reaction
3. temperatureAfter cooling
4. customUpon completion of the reaction
5. customthe solvent was slowly evaporated under vacuum
6. washwashed with water (3×500 mL)
7. customThe organic layer was dried
8. filtrationthe salts filtered
9. customthe solvent evaporated carefully under vacuum

ORD record

ord-bcf974819f8845118aa829256d9e8d38

Source dataset

uspto-grants-2006_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07151105B2