反応 #8403

反応方程式

dimethyl formamide

thionyl chloride

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

methylamine

→

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

溶媒

1,2-dichloroethane

ethanol

反応条件

後処理

1. 1
   温度at reflux until a clear, yellow 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 52.3 g (99%) of the title compound as light brown solid, which is used for further reaction without purification

実験手順

To a suspension of 50.0 g (0.25 mol) of 5-methyl-3-phenyl-isoxazole-4-carboxylic acid in 1.2 l of 1,2-dichloroethane (DCE) is added 1.9 ml dimethyl formamide (DMF) and 21.4 ml (0.3 mol, 1.2 eq.) of thionyl chloride. The mixture is stirred for 2 h at reflux until a clear, yellow solution is formed. The solution is cooled to room temperature and then slowly added to a 8M solution of methylamine in ethanol (146 ml) at 5° C. The suspension is poured onto methylene chloride, washed with sat. NaHCO3-solution, dried over Na2SO4 and concentrated. This yields 52.3 g (99%) of the title compound as light brown solid, which is used for further reaction without purification. Mass spectrum: m/z (M+H)+: 217.1

出典