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

HRID 883957Notes

Reaction equation

HRID 883957 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 dimethylsulfoxide (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 was washed with 10% sodium bicarbonate and 10% sodium chloride, then dried over anhydrous sodium sulfate. The drying agent was filtered and solvent was removed under vacuum leaving a red solid as the title compound, (1.45 g, 92%).

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

Sources & evidence

ORD record
ord-a396bf1764db4856add05c86e285ade4
Source dataset
uspto-grants-2012_08
Patent number
US08236950B2

Reaction notes

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