Methyl 4-chloroacetoacetate → HCID 22638557, compound
Reaction equation
[CH3:1][CH2:2][C:3]1[CH:4]=[C:5]([C:9]([NH2:11])=[S:10])[CH:6]=[CH:7][N:8]=1.Cl[CH2:13][C:14](=O)[CH2:15][C:16]([O:18][CH3:19])=[O:17]>CO>[CH2:2]([C:3]1[CH:4]=[C:5]([C:9]2[S:10][CH:13]=[C:14]([CH2:15][C:16]([O:18][CH3:19])=[O:17])[N:11]=2)[CH:6]=[CH:7][N:8]=1)[CH3:1]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of ethionamide (Aldrich) (1.65 g, 10.0 mmol) and methyl 4-chloroacetoacetate (Fluka) (1.41 g, 10.0 mmol) in 50 mL of anhydrous MeOH was heated at reflux for 18 h. The solvent was evaporated to give an oily residue that was purified by chromatography (gradient elution: 10-50% EtOAc in hexanes) to afford the title compound as a light brown oil. MS m/z: 263 (M+1). Calc'd for C13H14N2O2S: 262.08.