Ethanol → 2-(Dodecylthio)-aniline

HRID 21892

反応式

HRID 21892 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[SH:8].C(O)C.[OH-].[Na+].Br[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]>O>[CH2:26]([S:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[NH2:1])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH3:15]

参加物

6

反応物 4

HCID 702EthanolHCID 87132-AminothiophenolHCID 89191-BromododecaneHCID 14798Sodium Hydroxide

生成物 1

HCID 46703792-(Dodecylthio)-aniline収率 75%

試薬・触媒・溶媒 1

HCID 962Water溶媒

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).

後処理

  1. customInto a 2-liter 3-necked round bottomed flask equipped with condenser, stirrer
  2. temperatureheating mantle
  3. temperatureHeating
  4. temperaturethe solution heated
  5. temperatureat reflux overnight
  6. temperatureUpon cooling
  7. customsolvent was removed at reduced pressure and water (500 ml) and dichloromethane (500 ml)
  8. additionwere added
  9. customThe mixture was transferred to a 2-liter separatory funnel
  10. customthe layers separated
  11. washthe organic layer washed with 500 ml of aqueous sodium chloride solution
  12. dry with materialdried over anhydrous magnesium sulfate
  13. customwas removed at reduced pressure
  14. distillationthe material distilled under vacuum

出典と根拠

ORDレコード
ord-52d74d5b84944a6991c4b43912ef7c00
出典データセット
uspto-grants-1995_06
特許番号
US05426085

関連ノート

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