{[(2-Methyl-1-nitropropan-2-yl)sulfanyl]methyl}benzene → 2-benzylsulfanyl-2-methylpropan-1-amine

HRID 1033823Notes

Reaction equation

HRID 1033823 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

HCID 4235832-benzylsulfanyl-2-methylpropan-1-amineYield 46%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-93c31ce256744c6280bc9f304d831925
Source dataset
uspto-grants-1994_05
Patent number
US05312904

Reaction notes

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