Stannous Chloride → 5-Methyl-2-phenylsulfanyl-phenylamine

HRID 2197694Notes

Reaction equation

HRID 2197694 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[C:4]([N+:15]([O-])=O)[CH:3]=1.Cl[Sn]Cl>CCO>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)=[C:4]([NH2:15])[CH:3]=1

Participants

4

Reactant 2

HCID 24479Stannous ChlorideHCID 596452024-Methyl-2-nitro-1-phenylsulfanyl-benzene

Product 1

HCID 433496035-Methyl-2-phenylsulfanyl-phenylamineYield 82%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of the product from Example 1e (1.17 g, 7.0 mmol) in 25 mL of absolute EtOH and SnCl2 (3.58 g, 29.8 mmol) was stirred at room temperature for 16 h. Adjusted to pH 12 with 1N NaOH and extracted with EtOAc. Dried over Na2SO4, filtered and concentrated under vacuum giving the title compound (835 mg, 82%) 1H NMR (300 MHz, CDCl3) δ ppm: 2.30 (2, 3H) 6.62 (d, J=8.83 Hz, 1H) 6.69 (s, 1H) 7.10 (m, 3H) 7.21 (m, 2H) 7.54 (d, J=7.72 Hz, 2H).

Workup

  1. extractionAdjusted to pH 12 with 1N NaOH and extracted with EtOAc
  2. dry with materialDried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-05735070af364f9f806eed4665df22b1
Source dataset
uspto-grants-2012_12
Patent number
US08338605B2

Reaction notes

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