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

HRID 2427082Notes

Reaction equation

HRID 2427082 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-a6b6043e2d0f491995891e3a03b3c4b9
Source dataset
uspto-grants-2011_06
Patent number
US07968573B2

Reaction notes

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