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

HRID 2358529Notes

Reaction equation

HRID 2358529 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-d1cc24d45c934e388bc59944b50ab86c
Source dataset
uspto-grants-2010_07
Patent number
US07763731B2

Reaction notes

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