Benzene → HCID 19841450, compound

HRID 1638746Notes

Reaction equation

HRID 1638746 reaction equation
[Cl:1][C:2]1[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:3]=1[O:4][C:5]1[C:11]([CH3:12])=[CH:10][C:8]([NH2:9])=[CH:7][C:6]=1[CH3:13].C1C=CC=CC=1.[Cl:25]N1C(=O)CCC1=O>C(OCC)(=O)C>[Cl:25][C:10]1[C:11]([CH3:12])=[C:5]([O:4][C:3]2[CH:14]=[CH:15][C:16]([Cl:18])=[CH:17][C:2]=2[Cl:1])[C:6]([CH3:13])=[CH:7][C:8]=1[NH2:9]

Participants

5

Reactant 3

HCID 241BenzeneHCID 31398ChlorosuccinimideHCID 54037426HCID 54037426, compound

Product 1

HCID 19841450HCID 19841450, compoundYield 85.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Into a 200 milliliter three-necked, round bottom reaction flask was charged 6.76 grams (24.0 mmol) of 4-(2,4-dichlorophenoxy)-3,5-dimethyl aniline and 48 milliliters of benzene. N-chlorosuccinimide (3.85 grams, 28.8 mmol) was then added and the resultant heterogeneous mixture was stirred at room temperature for 1 hour. The reaction mixture was diluted with ethyl acetate, washed (2x) with saturated Na2SO3 solution and dried over Na2SO4. Concentration under reduced pressure afforded the crude product as a dark oil. This material was filtered through a short column of silica gel using 9:1 hexane: ethyl acetate as an eluant. Solvent removal under reduced pressure afforded 2-chloro-4-(2,4-dichlorophenoxy)-3,5-dimethylaniline (6.5 grams) contaminated with at least three other products. This material was placed in a Parr bottle and dissolved in toluene (50 milliliters). The Parr bottle was purged with nitrogen, 5% platinum on carbon (650 milligrams) was added and the mixture was hydrogenated for 1 hour at 40-50 psi and room temperature on a rocking Parr hydrogenator. Filtration through a pad of celite, solvent removal and flash chromatography (9:1 hexane: ethyl acetate afforded pure 2-chloro-4-(2,4-dichlorophenoxy)-3,5-dimethyl aniline (3.1 grams, 9.8 mmol, 41%) as a crystallized solid having a melting point of 89° C.-93° C. Elemental analysis of the crystalline solid indicated the following:

Workup

  1. washwashed (2x) with saturated Na2SO3 solution
  2. dry with materialdried over Na2SO4
  3. concentrationConcentration under reduced pressure
  4. customafforded the crude product as a dark oil
  5. filtrationThis material was filtered through a short column of silica gel using 9:1 hexane
  6. customSolvent removal under reduced pressure

Sources & evidence

ORD record
ord-aaadfaa117224915b32a0d6c56ebda74
Source dataset
uspto-grants-1989_11
Patent number
US04880838

Reaction notes

Loading…