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Sodium Iodide → 1-(4-Fluorobenzoyl)-2-oxo-3-pyrrolidinecarbonitrile

HRID 714777
Notes
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Reaction equation

HRID 714777 reaction equation
[C:1]([C:3]1[CH2:7][CH2:6][O:5][C:4]=1[NH:8][C:9](=[O:17])[C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=1)#[N:2].[I-].[Na+]>CN(C)C=O>[F:16][C:13]1[CH:14]=[CH:15][C:10]([C:9]([N:8]2[CH2:6][CH2:7][CH:3]([C:1]#[N:2])[C:4]2=[O:5])=[O:17])=[CH:11][CH:12]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 7655792N-(3-Cyano-4,5-dihydro-2-furanyl)-4-fluorobenzamide

Product 1

HCID 114361891-(4-Fluorobenzoyl)-2-oxo-3-pyrrolidinecarbonitrileYield 26%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of N-(3-cyano-4,5-dihydrofuran-2-yl)-4-fluorobenzamide (5.0 g) obtained in Step E in N,N-dimethylformamide (30 mL) was added sodium iodide (6.5 g), and the mixture was stirred at 150° C. for 30 min. The solvent was evaporated under reduced pressure, and to the residue was added ice water. The resulting solid was collected by filtration, and washed with water. The residue was purified by silica gel column chromatography (hexane/ethyl acetate), and the resulting solid was washed with diisopropyl ether to give the title compound (1.3 g).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. additionto the residue was added ice water
  3. filtrationThe resulting solid was collected by filtration
  4. washwashed with water
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)
  6. washthe resulting solid was washed with diisopropyl ether

Sources & evidence

ORD record
ord-53acff91ea2745cf9fbd875b5355a078
Source dataset
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09187453B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes