反応 #8405

反応方程式

DMF

thionyl chloride

3-methyl-5-phenyl-isoxazole-4-carboxylic acid

methylamine

→

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

溶媒

DCE

ethanol

反応条件

後処理

1. 1
   温度at reflux until a brown solution
2. 2
   その他is formed
3. 3
   workup.ADDITIONThe suspension is poured onto methylene chloride
4. 4
   洗浄washed with sat. NaHCO3-solution
5. 5
   乾燥dried over Na2SO4
6. 6
   濃縮concentrated
7. 7
   その他This yields 6.7 g (quant.) of the title compound as brown solid, which is used for further reactions without purification

実験手順

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

出典