反応 #2512

反応方程式

thionyl chloride

4-cyanobenzoic acid

o-anisidine

sodium hydroxide

→

title compound

収率 93.6%

4-Cyano-N-(2-methoxyphenyl)benzamide

収率 93.6%

溶媒

methylene chloride

DMF

benzene

反応条件

後処理

1. 1
   温度of heating
2. 2
   温度under reflux
3. 3
   その他After removing the solvent
4. 4
   その他by evaporation
5. 5
   その他to obtain a yellow solid which
6. 6
   温度with cooling in an ice bath
7. 7
   抽出the resulting mixture was extracted with methylene chloride
8. 8
   洗浄washed with 1N hydrochloric acid, water and saturated brine in that order
9. 9
   乾燥After drying on anhydrous magnesium sulfate
10. 10
    その他the solvent was removed by evaporation
11. 11
    その他the resulting light yellow solid was purified by recrystallization (methylene chloride-ether)

実験手順

In an atmosphere of dry air, 4-cyanobenzoic acid (1.5 g, 10 mmol) was dissolved in benzene (5 ml), and DMF (0.1 ml) and thionyl chloride (2.2 ml, 30 mmol) were added dropwise to the resulting solution at room temperature, followed by 30 minutes of heating under reflux. After removing the solvent by evaporation, the resulting residue was subjected to azeotropy using benzene (10 ml×2) to obtain a yellow solid which was subsequently dissolved in methylene chloride (10 ml) and mixed with o-anisidine (1.16 ml, 10 mmol) and 20% sodium hydroxide aqueous solution (4 ml) with cooling in an ice bath. After 20 minutes of stirring at the same temperature, the resulting mixture was extracted with methylene chloride and then washed with 1N hydrochloric acid, water and saturated brine in that order. After drying on anhydrous magnesium sulfate, the solvent was removed by evaporation, and the resulting light yellow solid was purified by recrystallization (methylene chloride-ether) to obtain 2.36 g (93.6%) of the title compound in the form of creamy-colored crystals.

出典