4-Chloroaniline → 1,2-Bis(4-chlorophenyl)-5-methylpyrrole

HRID 638797Notes

Reaction equation

HRID 638797 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH2:9][CH2:10][C:11](=O)[CH3:12])=[CH:4][CH:3]=1.[Cl:15][C:16]1[CH:22]=[CH:21][C:19]([NH2:20])=[CH:18][CH:17]=1>C1C=CC=CC=1>[Cl:15][C:16]1[CH:22]=[CH:21][C:19]([N:20]2[C:11]([CH3:12])=[CH:10][CH:9]=[C:8]2[C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 78124-ChloroanilineHCID 51687791-(4-Chlorophenyl)pentane-1,4-dione

Product 1

HCID 4569171,2-Bis(4-chlorophenyl)-5-methylpyrroleYield 39.45%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 1-(4-chlorophenyl)pentane-1,4-dione (5.0 g., 0.024 mol, as obtained in Step-1) and 4-chloroaniline (3.33 g, 0.026 mol) in benzene (5.0 ml) was refluxed either over molecular sieves or using a Dean Stark apparatus. After three hours, benzene was removed under reduced pressure and the residue dissolved in ethyl acetate, washed with water (2×100 ml.) and brine (1×50 ml). The ethyl acetate layer was dried over anhydrous sodium sulfate, and the solvent evaporated off. The solid so obtained was washed with hexane to give 2.83 g (39.45%) of the title compound.

Workup

  1. temperaturewas refluxed either over molecular sieves
  2. custombenzene was removed under reduced pressure
  3. dissolutionthe residue dissolved in ethyl acetate
  4. washwashed with water (2×100 ml.) and brine (1×50 ml)
  5. dry with materialThe ethyl acetate layer was dried over anhydrous sodium sulfate
  6. customthe solvent evaporated off
  7. customThe solid so obtained
  8. washwas washed with hexane

Sources & evidence

ORD record
ord-5252293331a143d4a8dd3dfb52e85592
Source dataset
uspto-grants-2010_04
Patent number
US07691837B2

Reaction notes

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