反应 #1244295

反应方程式

4-methyl-3-nitrobenzoic acid

N,N-dimethylformamide

N,N-di-n-propylamine

thionyl chloride

→

N,N-dipropyl-4-methyl-2-nitrobenzamide

溶剂

toluene

ethyl acetate

反应条件

后处理

1. 1
   温度at gentle reflux for four hours
2. 2
   workup.DISTILLATIONdistilled to approximately half the volume (67.77 g residual net weight)
3. 3
   其他to remove excess thionyl chloride
4. 4
   其他resulting in immediate formation of a slurry that
5. 5
   workup.STIRRINGwas stirred at ambient temperature overnight
6. 6
   其他This was then quenched into water (150 mL)
7. 7
   洗涤The organic layer was washed with cold 0.5 N hydrochloric acid (100 mL)
8. 8
   干燥with 5% aqueous sodium bicarbonate, dried (MgSO4)
9. 9
   其他evaporated
10. 10
    其他to give a colorless oil

实验过程

To a mixture of 4-methyl-3-nitrobenzoic acid (36.23 g, 0.2 mmol), N,N-dimethylformamide (5 mL), and toluene (85 mL) was added with stirring thionyl chloride (30 mL, 48.8 g, 0.41 mole). The mixture was stirred at gentle reflux for four hours, then distilled to approximately half the volume (67.77 g residual net weight) to remove excess thionyl chloride. This solution was cooled to 20° C., and 22.6 grams of it (nominally 6.67 mmol) was added to a solution of N,N-di-n-propylamine (22.0 g, 0.22 mole) in ethyl acetate (100 mL) resulting in immediate formation of a slurry that was stirred at ambient temperature overnight. This was then quenched into water (150 mL). The organic layer was washed with cold 0.5 N hydrochloric acid (100 mL), then with 5% aqueous sodium bicarbonate, dried (MgSO4) and evaporated to give a colorless oil weighing 16.55 g (94.0%). This was characterized by proton and carbon nmr, as well as electrospray mass spectrum (M+1 at m/e 265.1).

来源