Dimethylformamide → 3-Methyl-5-phenyl-isoxazole-4-carboxylic acid methylamide

Participants

Reaction Steps

To a suspension of 6.0 g (29.6 mmol) of 3-methyl-5-phenyl-isoxazole-4-carboxylic acid in 150 ml DCE is added 0.3 ml of DMF and 2.6 ml (35.5 mmol, 1.2 eq.) of thionyl chloride. The mixture is stirred for 2 h at reflux until a brown solution is formed. The solution is cooled to room temperature and then slowly added to a 8M solution of methylamine in ethanol (18 ml) at 5° C. The suspension is poured onto methylene chloride, washed with sat. NaHCO3-solution, dried over Na2SO4 and concentrated. This yields 6.7 g (quant.) of the title compound as brown solid, which is used for further reactions without purification. Mass spectrum: m/z (M+H)+: 217.2

Provenance & Evidence