Ethyl Acetate → 4-(2-Amino-4-nitro-phenylsulfanyl)-phenol

HRID 605162Notes

Reaction equation

HRID 605162 reaction equation
Cl[C:2]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:3]=1[NH2:4].[OH:12][C:13]1[CH:18]=[CH:17][C:16]([SH:19])=[CH:15][CH:14]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C(OCC)(=O)C>CN(C)C=O>[NH2:4][C:3]1[CH:5]=[C:6]([N+:9]([O-:11])=[O:10])[CH:7]=[CH:8][C:2]=1[S:19][C:16]1[CH:17]=[CH:18][C:13]([OH:12])=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 226912-Chloro-5-nitroanilineHCID 2401474-Mercaptophenol

Product 1

HCID 668084214-(2-Amino-4-nitro-phenylsulfanyl)-phenol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-Chloro-5-nitroaniline (3 g, 17.4 mmole), 4-hydroxythiophenol (2.4 g, 19.0 mmol), cesium carbonate (12.35 g, 38 mmol) in dimethylformamide (35 ml) was heated at 100° C. for 16 hours. Afterwards ice water (200 mL) was added to the solution and to the resultant slurry was added ethyl acetate (200 ml). The layers were separated and the organic layer was washed with 10% sodium bicarbonate and 10% sodium chloride, dried over anhydrous sodium sulfate. The drying agent was filtered and solvent was removed under vacuum leaving a yellow oil. The oil was purified by silica gel chromatography eluting with methylene chloride/methanol (97:3), to provide a yellow solid (4-(2-Amino-4-nitro-phenylsulfanyl)-phenol) (2.1g, 46%).

Workup

  1. customThe layers were separated
  2. washthe organic layer was washed with 10% sodium bicarbonate and 10% sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationThe drying agent was filtered
  5. customsolvent was removed under vacuum
  6. customleaving a yellow oil
  7. customThe oil was purified by silica gel chromatography
  8. washeluting with methylene chloride/methanol (97:3)

Sources & evidence

ORD record
ord-dace3570d59840688872489724b6f76f
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

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