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

HRID 2197757Notes

Reaction equation

HRID 2197757 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-d3ee3007613f471e8d63d47cac4bbb4c
Source dataset
uspto-grants-2012_12
Patent number
US08338605B2

Reaction notes

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