Pyrrole → 4,5-Dichloro-2-(3,4-dichlorophenyl)-1-(2-hydroxyethyl)-pyrrole-2-carbonitrile

HRID 1651690Notes

Reaction equation

HRID 1651690 reaction equation
[Cl:1][C:2]1[C:3](C#N)=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[C:10]([Cl:15])[CH:9]=2)[NH:5][C:6]=1[Cl:7].[CH3:18][C:19](C)([O-:21])C.[K+].BrC(O)C.[NH:28]1C=CC=[CH:29]1>O1CCOCC1.O.C(OCC)(=O)C>[Cl:1][C:2]1[CH2:3][C:4]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[C:10]([Cl:15])[CH:9]=2)([C:29]#[N:28])[N:5]([CH2:18][CH2:19][OH:21])[C:6]=1[Cl:7]

Participants

8

Reactant 4

HCID 8027PyrroleHCID 1835554,5-dichloro-2-(3,4-dichlorophenyl)-1H-pyrrole-3-carbonitrileHCID 14202443Ethanol, 1-bromo-HCID 23665647Potassium tert-butoxide

Product 1

HCID 190263774,5-Dichloro-2-(3,4-dichlorophenyl)-1-(2-hydroxyethyl)-pyrrole-2-carbonitrile

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

To a stirred mixture of 2.0 g (6.5 mmol) of 4,5-dichloro-2-(3,4-dichlorophenyl)-pyrrole-3-carbonitrile and 0.88 g (7.8 mmol) of potassium tert-butoxide heated at reflux in 50 mL of dioxane is added 0.98 g (7.8 mmol) of bromoethanol. The mixture is stirred at reflux for 12 hours, cooled, diluted with 50 mL of water, and extracted several times with chloroform. The combined chloroform extracts are dried over magnesium sulfate and concentrated in vacuo to leave a solid which, on warming and dissolving in ethyl acetate, deposits on cooling mostly starting pyrrole. Concentration of the mother liquor and recrystallization of the residual solid from 20% ethyl acetate in hexane gives 0.31 g of a white solid, mp 143°-145° C.; IR 5077A.

Workup

  1. temperatureheated
  2. temperatureat reflux for 12 hours
  3. temperaturecooled
  4. extractionextracted several times with chloroform
  5. dry with materialThe combined chloroform extracts are dried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customto leave a solid which
  8. temperatureon warming
  9. customConcentration of the mother liquor and recrystallization of the residual solid from 20% ethyl acetate in hexane

Sources & evidence

ORD record
ord-53a210bfaf204068b448828cd32b02aa
Source dataset
uspto-grants-1990_05
Patent number
US04929634

Reaction notes

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