Water → 5-Amino-1-[bis(4-fluorophenyl)methyl]-1H-pyrrole-3-carbonitrile

HRID 730432Notes

Reaction equation

HRID 730432 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([NH:16]/[CH:17]=[C:18](\[CH2:21][C:22]#[N:23])/[C:19]#[N:20])[C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.[O-]CC.[K+].O>O1CCCC1.C(O)C>[NH2:23][C:22]1[N:16]([CH:8]([C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)[C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)[CH:17]=[C:18]([C:19]#[N:20])[CH:21]=1

Participants

6

Reactant 3

HCID 962WaterHCID 23670592Potassium ethoxideHCID 69063437HCID 69063437, compound

Product 1

HCID 230746485-Amino-1-[bis(4-fluorophenyl)methyl]-1H-pyrrole-3-carbonitrile

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2E)-2-({[bis(4-fluorophenyl)methyl]amino}methylene)butanedinitrile (13.9 g, 45.1 mmol) in tetrahydrofuran (48 ml) and ethanol (48 ml) was slowly added potassium ethoxide (6.67 g, 79.2 mmol), which 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-42a05f27fc5242338c475acdb3ce56de
Source dataset
uspto-grants-2009_09
Patent number
US07582651B2

Reaction notes

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