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

HRID 2358592Notes

Reaction equation

HRID 2358592 reaction equation
Cl[C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[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>CS(C)=O>[NH2:6][C:5]1[CH:7]=[CH:8][C:2]([S:19][C:16]2[CH:17]=[CH:18][C:13]([OH:12])=[CH:14][CH:15]=2)=[C:3]([N+:9]([O-:11])=[O:10])[CH:4]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 124774-Chloro-3-nitroanilineHCID 2401474-Mercaptophenol

Product 1

HCID 668084374-(4-Amino-2-nitro-phenylsulfanyl)-phenolYield 95.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 4-chloro-3-nitro aniline (1.0 g, 5.79 mmol), 4-hydroxythiophenol (0.75 g, 6.00 mmol), cesium carbonate (3.9 g, 12 mmol) in DMSO (10 mL) was heated at 100° C. for 16 hours. Afterwards ice water (50 mL) was added to the solution and the resultant slurry was treated with ethyl acetate (100 mL). The layers were separated and the organic layer washed with 10% sodium bicarbonate and 10% sodium chloride, then dried over anhydrous sodium sulfate. The drying agent was filtered and concentrated under vacuum giving the title compound as a red solid (1.45 g, 92%).

Workup

  1. customThe layers were separated
  2. washthe organic layer washed with 10% sodium bicarbonate and 10% sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationThe drying agent was filtered
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-47546b6fc9e94818b6b8b8ad62a6faa0
Source dataset
uspto-grants-2010_07
Patent number
US07763731B2

Reaction notes

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