Methyl iodide → HCID 53686750, compound

Participants

Reaction Steps

A mixture of 5.0 g (0.015 mole) of N,N-dimethylalpha-ethoxycarbonyl-beta-hydroxy-2,4-dichlorocinnamamide and 4.14 g (0.03 mole) anhydrous powdered K2CO3 in 100 ml MEK was heated to reflux for 30 minutes then cooled to room temperature. To the slurry was added 2.44 g (0.0165 mole) CH3I dropwise. The reaction mixture was stirred at room temperature an additional 30 minutes then heated to reflux for 2 hours and then cooled again to room temperature. The reaction was worked-up by diluting with 200 ml ether washing successively with water (2×100 ml) and 10% NaHCO3 (2×100 ml) and then drying the organic phase over anhydrous MgSO4, filtering, and stripping off the ether to yield 5.2 g of a semi-solid. The semi-solid was crystallized from ether/hexanes to yield 4.0 g of the product, mp 88°-92°.

Provenance & Evidence