Acetonitrile → 1-(6-(2-Cyanoacetyl)-2-benzothiazolyl)-3-ethylurea

Participants

Reaction Conditions

Reaction Steps

A solution of 1-(6-ethoxycarbonyl-2-benzothiazolyl)-3-ethylurea (1.20 g, 4.09 mmol) in 5 mL of anhydrous DMF was treated with 2 mL of acetonitrile, cooled down to about 0° C., followed by treatment with 1 M LiHMDS in THF (13.1 mL, 13.1 mmol, 3.2 eq). It was stirred at the temperature for about 0.5 hour, then warmed up to room temperature, and stirred for another 4 hours. More LiHMDS (4 mL, 4.0 mmol, 1.0 eq) was added after the first hour. The mixture was quenched with MeOH and water, concentrated, and purified by flash chromatography on SiO2 with MeOH and methylene chloride (1/50) to give the desired compound 0.640 g (54%). LC/MS 288.9 (M+1); LC retention time 2.56 min.

Provenance & Evidence