Methanol → m-ethylphenyl-N-methylcyanamide

Participants

Reaction Steps

A suspension of 3-ethylphenylcyanamide (4.65 g, 31.8 mmol) and sodium hydride (2.55 g of 80% NaH in mineral oil suspension, 63.6 mmol of NaH) in dried THF was heated at reflux for 3 hours. The reaction mixture was cooled in an ice bath and methyl iodide (11.28 g, 79.5 mmol) was added dropwise with stirring to the mixture. The reaction mixture was then allowed to stir for 15 hours, followed by the successive addition of MeOH (10 mL). The reaction mixture was then concentrated to dryness to give the crude product. Distilled water (40 mL) was added to this crude product and the aqueous mixture was extracted with CH2Cl2 (4×40 mL). The combined organic extracts were washed with water (3×30 mL) and then dried over MgSO4. The solvent was removed to afford the crude product as an amber syrup. Flash chromatography (SiO2, CH2Cl2) of the crude product afforded 4.2 g (75% yield) of the desired product.

Provenance & Evidence