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

HRID 607206Notes

Reaction equation

HRID 607206 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)-phenolYield 46%

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 as the title compound (2.1 g, 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-464b8c0f0d594079837483b259aecc5c
Source dataset
uspto-grants-2011_03
Patent number
US07915411B2

Reaction notes

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