{[(2-Methyl-1-nitropropan-2-yl)sulfanyl]methyl}benzene → 2-Methyl-2-(benzylthio)propylamine

HRID 1033823ノート

反応式

HRID 1033823 の反応式
[CH2:1]([S:8][C:9]([CH3:15])([CH3:14])[CH2:10][N+:11]([O-])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>CCOCC>[CH2:1]([S:8][C:9]([CH3:15])([CH3:14])[CH2:10][NH2:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

4

反応物 2

HCID 14613816{[(2-Methyl-1-nitropropan-2-yl)sulfanyl]methyl}benzeneHCID 21226445Aluminium lithium hydride

生成物 1

HCID 4235832-Methyl-2-(benzylthio)propylamine収率 46%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒2 回

実験手順

A solution of 2-benzylthio-1-nitro-2-methylpropane (19 g) in dry ether (75 cm3) was added dropwise over a period of about 1 h to a stirred suspension of lithium aluminium hydride (9.6 g) in dry ether (500 cm3), cooled in an ice bath. When the addition was complete the mixture was heated under reflux for an additional hour. Excess lithium aluminium hydride was destroyed by the careful addition of water, and then an aqueous solution of sodium potassium tartrate (500 cm3, 20% w/w) was added. The mixture was stirred until the solids had dissolved and the ether layer was then separated. The aqueous solution was then extracted with ether (3×50 cm3) and the combined extracts then dried (MgSO4). Removal of the ether under reduced pressure gave the crude product which was purified via recrystallisation of its hydrochloride salt from isopropanol. The purified amine (7.5 g, 46%) was obtained as a yellow oil.

後処理

  1. temperaturecooled in an ice bath
  2. additionWhen the addition
  3. temperaturewas heated
  4. temperatureunder reflux for an additional hour
  5. customExcess lithium aluminium hydride was destroyed by the careful addition of water
  6. additionan aqueous solution of sodium potassium tartrate (500 cm3, 20% w/w) was added
  7. dissolutionhad dissolved
  8. customthe ether layer was then separated
  9. extractionThe aqueous solution was then extracted with ether (3×50 cm3)
  10. dry with materialthe combined extracts then dried (MgSO4)
  11. customRemoval of the ether under reduced pressure
  12. customgave the crude product which
  13. customwas purified via recrystallisation of its hydrochloride salt from isopropanol

出典と根拠

ORDレコード
ord-93c31ce256744c6280bc9f304d831925
出典データセット
uspto-grants-1994_05
特許番号
US05312904

反応ノート

読み込み中…