Phosphorus oxychloride → 4,5-Dichloro-1-(chloromethyl)-2-(3,4-dichlorophenyl)pyrrol-3-carbonitrile

HRID 654133Notes

Reaction equation

HRID 654133 reaction equation
[Cl:1][C:2]1[N:3]([CH2:18]NC(=O)C)[C:4]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]([Cl:17])[CH:11]=2)=[C:5]([C:8]#[N:9])[C:6]=1[Cl:7].P(Cl)(Cl)([Cl:25])=O>O>[Cl:7][C:6]1[C:5]([C:8]#[N:9])=[C:4]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]([Cl:17])[CH:11]=2)[N:3]([CH2:18][Cl:25])[C:2]=1[Cl:1]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 19888638N-{[2,3-dichloro-4-cyano-5-(3,4-dichlorophenyl)pyrrol-1-yl]methyl}acetamide

Product 1

HCID 198886374,5-Dichloro-1-(chloromethyl)-2-(3,4-dichlorophenyl)pyrrol-3-carbonitrileYield 78%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of N-{[2,3-dichloro-4-cyano-5-(3,4-dichlorophenyl)pyrrol-1-yl]methyl}acetamide (3.2 g, 0.0085 mol) and phosphorus oxychloride (6.51 g, 4 mL, 0.0424 mol) is heated at reflux temperature for 40 minutes, cooled, diluted with water and extracted with ethyl acetate. The combined organic extracts are washed sequentially with water and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to obtain a solid. Recrystallization of the solid from an ethyl acetate/heptane solution gives the title product as a pale brown solid (2.35 g, mp 153°-156.0° C.) which is identified by IR and NMR spectral analyses.

Workup

  1. temperatureis heated
  2. temperatureat reflux temperature for 40 minutes
  3. temperaturecooled
  4. extractionextracted with ethyl acetate
  5. washThe combined organic extracts are washed sequentially with water and brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customto obtain a solid
  9. customRecrystallization of the solid from an ethyl acetate/heptane solution

Sources & evidence

ORD record
ord-68756b3ddc04470482f86913d6c4577a
Source dataset
uspto-grants-1992_07
Patent number
US05130328

Reaction notes

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