Dimethyl Sulfate → HCID 53633407, compound

Participants

Reaction Steps

A solution of 3-(dimethylamino)-2-(methoxymethyl)-2-propenal, (E)-- and (Z)-- (53.06 g, 0.37 mol) and sodium hydroxide solution (29.7 g, 50%, 0.37 mol) in methanol (60 mL) is refluxed for 20 minutes and concentrated in vacuo to obtain a white solid. A solution of the solid in water (250 mL) is treated dropwise with dimethyl sulfate (46.75 g, 0.37 mol), stirred at room temperature for one hour and extracted with methylene chloride. The organic extract is dried over anhydrous sodium sulfate, concentrated in vacuo and distilled to give the title product as a colorless liquid (19.66 g, bp 80° C./0.5 mm Hg, 41% yield).

Provenance & Evidence