Methanol → HCID 69417510, compound

Participants

Reaction Conditions

Reaction Steps

To a dried round bottom flask was added NaH (3.73 g in 60% disp.; 93.3 mmol), DMF (100 mL), and methanol (3.78 mL; 93.3 mmol) under a nitrogen atmosphere. To this suspension was added a solution of 2-cyanoacetamide (3.92 g; 46.6 mmol) in DMF (30 mL) via syringe. Then a solution of the crude product of Step B (42.4 mmol) in DMF (30 mL) was added via syringe. The resulting reaction mixture was heated to 95° C. and stirred for 3 hours. The reaction was quenched with saturated aq. NaHSO4 solution and extracted with methylene chloride (3×). The combined extracts were dried (Na2SO4), filtered, and concentrated in vacuo. Purification was done by trituration in ethanol. The precipitate was collected and washed with cold ethanol to afford the desired product: m/e=355 (M+1) Rt=3.3 min on LCMS.

Provenance & Evidence