Potassium Carbonate → HCID 15005406, compound

Reaction equation

[CH:1]([C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][CH:4]=1)=[O:2].[N+:11]([CH:13](S(C1C=CC(C)=CC=1)(=O)=O)[CH3:14])#[C-:12].C(=O)([O-])[O-].[K+].[K+]>CO>[CH3:14][C:13]1[N:11]=[CH:12][O:2][C:1]=1[C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][CH:4]=1

Participants

Procedure

4-Formylbenzonitrile (1.61 g, 12.3 mmol), 1-(1-isocyanoethylsulfonyl)-4-methylbenzene (2.58 g, 12.3 mmol), and potassium carbonate (3.39 g, 24.5 mmol) in methanol (60 mL) was heated to reflux overnight. The reaction mixture was cooled and the volatiles evaporated. The residue was partitioned between water and ethyl acetate. The organic phase was washed with water and brine, dried over Na2SO4, filtered, and evaporated. The solid was chromatographed on silica gel, eluting with 10% to 50% ethyl acetate:hexanes to afford 1.70 g (75% yield) of the title compound as a white solid.