Tetrahydrofuran → 2-(Methylthio)benzylamine

HRID 1954769Notes

Reaction equation

HRID 1954769 reaction equation
[CH3:1][S:2][C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[C:5]#[N:6].[H-].[Al+3].[Li+].[H-].[H-].[H-].C1COCC1.[OH-].[Na+]>CCOCC.O>[CH3:1][S:2][C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[CH2:5][NH2:6]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 1387812-(Methylthio)benzonitrileHCID 21226445Aluminium lithium hydride

Product 1

HCID 27369812-(Methylthio)benzylamine

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 2-(methylthio)benzonitrile (29.8 g) in dry ether (150 ml) was added dropwise to a stirred suspension of lithium aluminium hydride (1.16 g) in dry ether (360ml) under nitrogen. A thick gum formed which was dissolved by the addition of dry THF (100 ml). The mixture was stirred at room temperature for 2 hours. Water (12 ml) was then carefully added followed by a 15% aqueous solution of sodium hydroxide (36 ml) and more water (12 ml). The mixture was filtered, the filtrate washed with water, dried and evaporated in vacuo. The residue was distilled in vacuo to give a colourless oil. Yield=20.9 g.

Workup

  1. customA thick gum formed which
  2. filtrationThe mixture was filtered
  3. washthe filtrate washed with water
  4. customdried
  5. customevaporated in vacuo
  6. distillationThe residue was distilled in vacuo
  7. customto give a colourless oil

Sources & evidence

ORD record
ord-db817dd51ed94672a4fc6fdb7898191b
Source dataset
uspto-grants-2000_09
Patent number
US06124288

Reaction notes

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