Acetic Acid → 1-(2,6-Dichlorophenyl)-1H-pyrrole

HRID 251972Notes

Reaction equation

HRID 251972 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([Cl:9])[C:3]=1[NH2:4].CO[CH:12]1[CH2:16][CH2:15][CH:14](OC)O1.C(O)(=O)C>O>[Cl:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([Cl:9])[C:3]=1[N:4]1[CH:12]=[CH:16][CH:15]=[CH:14]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 118462,6-DichloroanilineHCID 790982,5-Dimethoxytetrahydrofuran

Product 1

HCID 207882021-(2,6-Dichlorophenyl)-1H-pyrroleYield 83.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 5 g of 2,6-dichloroaniline, 4.5 g of 2,5-dimethoxytetrahydrofuran and 30 ml of acetic acid was heated to reflux for 10 hours. The reaction mixture was allowed to cool, poured into water, and extracted with ethyl acetate two times. The organic layers were combined, washed successively with water and an aqueous saturated sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel chromatography to obtain 5.45 g of 1-(2,6-dichlorophenyl)-1H-pyrrole of the formula:

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 10 hours
  3. temperatureto cool
  4. extractionextracted with ethyl acetate two times
  5. washwashed successively with water
  6. dry with materialan aqueous saturated sodium chloride solution, dried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-13168e9060b74d3393cfa02a32df9201
Source dataset
uspto-grants-2011_01
Patent number
US07867949B2

Reaction notes

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