反応 #725875

反応方程式

diethylamine

thionyl chloride

benzoic acid

benzoic acid

→

N,N-diethyl benzamide

溶媒

H2O

反応条件

後処理

1. 1
   workup.DISSOLUTIONdissolved
2. 2
   その他Excess thionyl chloride was removed under reduced pressure
3. 3
   その他leaving the crude acid chloride as a low melting solid which
4. 4
   その他was used without further purification
5. 5
   workup.DISSOLUTIONThe crude acid chloride was dissolved in CH2Cl2(20 mL)
6. 6
   workup.ADDITIONTo this stirred solution was added triethylamine (4 mL)
7. 7
   温度to warm to room temperature
8. 8
   その他The reaction mixture was transferred to a separatory funnel
9. 9
   その他The organic layer was separated
10. 10
    洗浄washed with 5% HCl (2×25 mL), H2O (25 ml)
11. 11
    乾燥dried over Na2SO4
12. 12
    その他The solvent was removed under reduced pressure

実験手順

A mixture of thionyl chloride (6 mL) and the benzoic acid was heated at reflux until the starting benzoic acid dissolved. Excess thionyl chloride was removed under reduced pressure leaving the crude acid chloride as a low melting solid which was used without further purification. The crude acid chloride was dissolved in CH2Cl2(20 mL) and cooled to −10° C. To this stirred solution was added triethylamine (4 mL), followed by the dropwise addition of diethylamine (1.4 equivalents). The heterogeneous reaction mixture was allowed to warm to room temperature and was stirred for 30 minutes. The reaction mixture was transferred to a separatory funnel containing H2O (20 mL). The organic layer was separated and washed with 5% HCl (2×25 mL), H2O (25 ml), and dried over Na2SO4. The solvent was removed under reduced pressure to afford the product N,N-diethyl benzamide.

出典