Thioacetamide → Ethyl 2-methyl-5-(1-methylethyl)-1,3-thiazole-4-carboxylate
Reaction equation
[C:1]([NH2:4])(=[S:3])[CH3:2].Br[CH:6]([CH:14]([CH3:16])[CH3:15])[C:7](=O)[C:8]([O:10][CH2:11][CH3:12])=[O:9]>C(O)C>[CH3:2][C:1]1[S:3][C:6]([CH:14]([CH3:16])[CH3:15])=[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[N:4]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
To a solution of thioacetamide (158 mg) in ethanol (20 ml) was added ethyl 3-bromo-4-methyl-2-oxopentanoate (500 mg) in ethanol (0.5 ml). Molecular sieves (100 mg) were added and the mixture was heated at 80° C. for 18 h. The mixture was filtered, washing with ethanol (5 ml) and the solvent removed in vacuo. The residue triturated with DCM and the solid removed by filtration. The filtrate was concentrated to ˜5 ml and purified by column chromatography on silica gel (10 g silica), eluting with a gradient of 0-100% ethyl acetate in cyclohexane to give the title compound as a yellow oil (280 mg).