Stannous Chloride → 2-Benzyloxy-4-methylsulfanylmethylphenylamine

HRID 660688Notes

Reaction equation

HRID 660688 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([CH2:15][S:16][CH3:17])[CH:12]=[CH:11][C:10]=1[N+:18]([O-])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[Sn]Cl>CCO>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([CH2:15][S:16][CH3:17])[CH:12]=[CH:11][C:10]=1[NH2:18])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 24479Stannous ChlorideHCID 688400562-Benzyloxy-4-methylsulfanylmethyl-1-nitrobenzene

Product 1

HCID 689977902-Benzyloxy-4-methylsulfanylmethylphenylamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 2-benzyloxy-4-methylsulfanylmethyl-1-nitrobenzene (900 mg, 3.11 mmol) EtOH (80 mL) is added SnCl2 (3.53 g, 18.7 mmol) and the solution is refluxed for 2 h. After the mixture cools to RT the EtOH is removed under reduced pressure and EtOAc is added. The solution is washed with 1N NaOH, water, brine and dried over sodium sulfate. The solvent is removed under reduced pressure and the residue is purified by flash chromatography using hexane/EtOAc (5:1) as eluent to give the title compound as a yellow liquid. NMR (CDCl3): 7.44-7.31 (m, 5H), 6.85 (d, J=1.77 Hz, 1H), 6.72-6.70 (dd, J=1.77 Hz, 7.83 Hz, 1H), 6.66-6.64 (d, J=7.84 Hz, 1H), 5.08 (s, 2H), 3.59 (s, 2H), 1.95 (s, 3H): (M+1)+=260.

Workup

  1. temperaturethe solution is refluxed for 2 h
  2. customcools to RT
  3. customis removed under reduced pressure and EtOAc
  4. additionis added
  5. washThe solution is washed with 1N NaOH, water, brine
  6. dry with materialdried over sodium sulfate
  7. customThe solvent is removed under reduced pressure
  8. customthe residue is purified by flash chromatography

Sources & evidence

ORD record
ord-969312c8d9c04a05a677482749c073c5
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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