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

HRID 883843Notes

Reaction equation

HRID 883843 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 7e (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, 3 H) 6.62 (d, J=8.83 Hz, 1 H) 6.69 (s, 1 H) 7.10 (m, 3 H) 7.21 (m, 2 H) 7.54 (d, J=7.72 Hz, 2 H).

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-8fb54a29e040440f825190c8ad1dd869
Source dataset
uspto-grants-2012_08
Patent number
US08236950B2

Reaction notes

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