Ethanol → 4-Chloro-2-(p-chlorophenyl)-1-(ethoxymethyl)-5-(trifluoromethyl)pyrrole-3-carbonitrile

HRID 2379431

Reaction equation

HRID 2379431 reaction equation
[Cl:1][C:2]1[C:3]([C:20]#[N:21])=[C:4]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)[N:5]([CH2:11]Cl)[C:6]=1[C:7]([F:10])([F:9])[F:8].[O-:22][CH2:23][CH3:24].[Na+].C(O)C>O1CCCC1.[O-]CC.[Na+].O>[Cl:1][C:2]1[C:3]([C:20]#[N:21])=[C:4]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)[N:5]([CH2:11][O:22][CH2:23][CH3:24])[C:6]=1[C:7]([F:10])([F:9])[F:8]

Participants

7

Reactant 3

HCID 702EthanolHCID 2723922Sodium ethoxideHCID 110356014-Chloro-1-(chloromethyl)-2-(p-chlorophenyl)-5-(trifluoromethyl)pyrrole-3-carbonitrile

Product 1

HCID 111112464-Chloro-2-(p-chlorophenyl)-1-(ethoxymethyl)-5-(trifluoromethyl)pyrrole-3-carbonitrileYield 60%

Reagents, catalysts & solvents 3

HCID 2723922Sodium ethoxideCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-chloro-1-(chloromethyl)-2-(p-chlorophenyl)-5-(trifluoromethyl)pyrrole-3-carbonitrile (2.6 g, 0.0074 mol) in tetrahydrofuran is treated with sodium ethoxide as a 21% wt/wt solution in denatured ethanol (3.6 mL, 0.0096 mol), stirred at room temperature for 1 hour, treated with an additional 2-3 drops of the sodium ethoxide solution, heated at reflux temperature for 1 hour, cooled and poured in water. The resultant precipitate is filtered, dried and recrystallized from isopropanol to afford the title product as a white solid, 1.6 g (60% yield), mp 104.0°-104.5 C.

Workup

  1. temperatureheated
  2. temperatureat reflux temperature for 1 hour
  3. temperaturecooled
  4. filtrationThe resultant precipitate is filtered
  5. customdried
  6. customrecrystallized from isopropanol

Sources & evidence

ORD record
ord-82d875e4f8b14386b9d6db11e516a684
Source dataset
uspto-grants-1994_11
Patent number
US05362746

Linked notes

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