反応 #50170

反応方程式

1-bromododecane

2-aminothiophenol

ethanol

sodium hydroxide

→

2-(dodecylthio)aniline

収率 75.0%

溶媒

water

反応条件

後処理

1. 1
   その他Into a 2-liter 3-necked round bottomed flask equipped with condenser, stirrer
2. 2
   温度heating mantle
3. 3
   温度Heating
4. 4
   温度the solution heated
5. 5
   温度at reflux overnight
6. 6
   温度Upon cooling
7. 7
   その他solvent was removed at reduced pressure and water (500 ml) and dichloromethane (500 ml)
8. 8
   workup.ADDITIONwere added
9. 9
   その他The mixture was transferred to a 2-liter separatory funnel
10. 10
    その他the layers separated
11. 11
    洗浄the organic layer washed with 500 ml of aqueous sodium chloride solution
12. 12
    乾燥dried over anhydrous magnesium sulfate
13. 13
    その他was removed at reduced pressure
14. 14
    workup.DISTILLATIONthe material distilled under vacuum

実験手順

Into a 2-liter 3-necked round bottomed flask equipped with condenser, stirrer and heating mantle, were placed 125.0 g (1.0 mol) of 2-aminothiophenol, 350 ml of ethanol and 40 g (1.0 mol) of sodium hydroxide dissolved in 40 ml of water. Stirring was begun and after 15 min, 249.24 g (1.0 mol) of 1-bromododecane was added. Heating was begun and the solution heated at reflux overnight. Upon cooling, solvent was removed at reduced pressure and water (500 ml) and dichloromethane (500 ml) were added. The mixture was transferred to a 2-liter separatory funnel and the layers separated. The aqueous layer was discarded, the organic layer washed with 500 ml of aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The crude material was passed through a bed of silica, solvent was removed at reduced pressure, and the material distilled under vacuum to afford 220 g (75%) of 2-(dodecylthio)aniline (b.p. 180° C. at 0.25 mm).

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