Water → 5-Amino-1-((4-fluorophenyl)(phenyl)methyl)-1H-pyrrole-3-carbonitrile

HRID 730424Notes

Reaction equation

HRID 730424 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([NH:15][CH:16]=[C:17]([CH2:20][C:21]#[N:22])[C:18]#[N:19])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.[O-]CC.[K+].O>O1CCCC1.C(O)C>[NH2:22][C:21]1[N:15]([CH:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:16]=[C:17]([C:18]#[N:19])[CH:20]=1

Participants

6

Reactant 3

HCID 962WaterHCID 23670592Potassium ethoxideHCID 690558642-({[(4-Fluorophenyl)(phenyl)methyl]amino}methylidene)butanedinitrile

Product 1

HCID 690583295-Amino-1-((4-fluorophenyl)(phenyl)methyl)-1H-pyrrole-3-carbonitrile

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-({[(4-fluorophenyl)(phenyl)methyl]amino}methylene)butanedinitrile (13.9 g, 47.7 mmol) in tetrahydrofuran (50 ml) and ethanol (50 ml) was slowly added potassium ethoxide (7.05 g, 83.8 mmol), the mixture was stirred at room temperature for 1 hour and poured into iced water. The product was extracted with ethyl acetate, the extract was washed with water, dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure to give the objective product as oily matter.

Workup

  1. extractionThe product was extracted with ethyl acetate
  2. washthe extract was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customto give the objective product as oily matter

Sources & evidence

ORD record
ord-3fa949b04f154c71aa98cf877af98d0e
Source dataset
uspto-grants-2009_09
Patent number
US07582651B2

Reaction notes

Loading…