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

HRID 607144Notes

Reaction equation

HRID 607144 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 5H (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-116835e9eb274a158ab85ec9cc970fe2
Source dataset
uspto-grants-2011_03
Patent number
US07915411B2

Reaction notes

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