Methyl iodide → HCID 627529, compound

Participants

Reaction Steps

3-oxo-3-phenylpropanenitrile (0.725 g, 5.0 mmol) was added to a suspension of potassium carbonate (1.98 g, 15.0 mmol) in N,N-dimethylformide (4.5 mL) and allowed to stir at ambient temperature. After 10 minutes, carbon disulfide (0.57 g, 7.5 mmol) was added in one portion and the resulting mixture stirred at ambient temperature for an additional 10 minutes then a solution of ethyl 2-chloroacetate (0.61 g, 5.0 mmol) in N,N-dimethylformide (5.0 mL) was added. After 1 hour, a solution of iodomethane (0.78 g, 5.0 mmol) in N,N-dimethylformide (2 mL) was added in a dropwise fashion then, after 30 minutes, the mixture was poured onto water and the resulting mixture was stirred for 16 hours to afford a suspension of the title product. The resulting precipitate was collected by filtration, washed with water (10 mL) and dried in vacuo overnight. The title product was obtained as a white solid (0.86 g, 56% yield). MS m/z: 326.89, 328.89 [M+Na]+.

Provenance & Evidence