Water → 5-Chloro-2-nitrodiphenylamine

HRID 1496964Notes

Reaction equation

HRID 1496964 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4](F)[CH:3]=1.[NH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+].O>CS(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([CH:3]=1)[NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6115AnilineHCID 11430Potassium CarbonateHCID 696914-Chloro-2-fluoro-1-nitrobenzene

Product 1

HCID 1176355-Chloro-2-nitrodiphenylamine

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
50 °C

Procedure

4-chloro-2-fluoronitrobenzene (250 mg), aniline (0.40 mL) and potassium carbonate (500 mg) were dissolved in dimethyl sulfoxide (1.5 mL) and stirred at 50° C. overnight. The mixture was added with water, extracted with ethyl acetate, and the organic layer was washed with saturated brine, and the water was removed with sodium sulfate. The reaction solution was removed of the solvent by distillation under reduced pressure, and the subsequent reaction was proceeded without further purification of the thus obtained compound.

Workup

  1. extractionextracted with ethyl acetate
  2. washthe organic layer was washed with saturated brine
  3. customthe water was removed with sodium sulfate
  4. customThe reaction solution was removed of the solvent by distillation under reduced pressure
  5. customthe subsequent reaction
  6. customwas proceeded without further purification of the thus obtained compound

Sources & evidence

ORD record
ord-be6fe9f2d8924de3acbbb0d7c4798f9a
Source dataset
uspto-grants-2015_12
Patent number
US09199944B2

Reaction notes

Loading…