Sodium Hydroxide → 3,5-Dichloro-4-(napthalen-2-ylsulfanyl)-phenylamine

HRID 1865493Notes

Reaction equation

HRID 1865493 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[C:4]([Cl:11])[C:3]=1[S:12][C:13]1[CH:22]=[CH:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=1.O.O.[Sn](Cl)Cl.[OH-].[Na+]>CCOC(C)=O>[Cl:11][C:4]1[CH:5]=[C:6]([NH2:8])[CH:7]=[C:2]([Cl:1])[C:3]=1[S:12][C:13]1[CH:22]=[CH:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 61436Stannous chloride dihydrateHCID 221488772-(2,6-Dichloro-4-nitro-phenylsulfanyl)-napthalene

Product 1

HCID 221488343,5-Dichloro-4-(napthalen-2-ylsulfanyl)-phenylamineYield 84%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a 0.1M solution 2-(2,6-Dichloro-4-nitro-phenylsulfanyl)-napthalene (89) (774 mg, 2.2 mmol), in EtOAc was added tin(II) chloride dihydrate, obtained from Aldrich, (2.49 g, 11.05 mmol). The resulting mixture was refluxed for 2 hour. The crude reaction mixture was cooled to ambient temperature and excess 2M aqueous NaOH was added and allowed to stir for 15 minutes. Solid tin salts precipitated from the solution, were filtered off through a pad of celite and washed with EtOAc (200 mL). The organic layer was washed twice with brine (200 mL), dried over Na2SO4, and concentrated under vacuum to yield 592 mg (84%) of (90) which was used without further purification.

Workup

  1. temperatureThe resulting mixture was refluxed for 2 hour
  2. customThe crude reaction mixture
  3. customSolid tin salts precipitated from the solution
  4. filtrationwere filtered off through a pad of celite
  5. washwashed with EtOAc (200 mL)
  6. washThe organic layer was washed twice with brine (200 mL)
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-7b8a6bb09213405491eabfd4f5c08ae1
Source dataset
uspto-grants-2009_12
Patent number
US07626033B2

Reaction notes

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